TETRA-NUCLEAR NEUTRAL COPPER (I) COMPLEXES

Abstract

The invention relates to tetra-nuclear neutral copper (I) complexes of Formula (A) that have a cubane-like structure, wherein said complexes comprise phosphine ligands which bear one or more aldehyde or ester groups. Furthermore, the present invention refers to methods for generating such copper (I) complexes of Formula (A) and to uses thereof. Each L is independently from each other a ligand that has a structure of Formula (A1): P(Ar).sub.m(CHR2-CHR1-CO—Y-Rx).sub.n.

##STR00001##

Claims

1. A copper (I) complex of Formula (A) ##STR00062## wherein: each Cu is copper (I); each X is independently from each other halogen; each L is independently from each other a ligand that has a structure of Formula (A1):
P(Ar).sub.m(CHR2-CHR1-CO—Y-Rx).sub.n  (A1), wherein: P is phosphorous; each Ar is independently from each other an unsubstituted or substituted aryl residue; each R1 is independently from each other hydrogen, —R.sup.a—R.sup.b, —O—R.sup.b, —R.sup.a—CO—O—R.sup.b—R.sup.a—O—R.sup.b, —R.sup.a—CO—NH—R.sup.b, —R.sup.a—NH—CO—R.sup.b, —R.sup.a—NH—R.sup.b, —R.sup.a—CO—R.sup.b, deuterium, or halogen; each R2 is independently from each other hydrogen, —R.sup.a—CO—O—R.sup.b, —R.sup.a—O—CO—R.sup.b, —R.sup.a—CO—NH—R.sup.b, —R.sup.a—NH—CO—R.sup.b, —R.sup.a—NH—R.sup.b, or —R.sup.a—CO—R.sup.b, deuterium, or halogen; Y is O, NH or a bond to a carbon atom of residue Rx or is N bound to two independent Rx Rx is an unsubstituted or substituted hydrocarbon residue comprising from 1 to 30 carbon atoms, a polymeric moiety, or a solid support, wherein Rx may optionally be or contribute to a linker that interconnects two ligands L with another; m is an integer from 0 to 2; n is an integer from 1 to 3; the sum of n and m is 3; R.sup.a at each occurrence independently from each other is a single bond, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)alkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkinylene residue, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)cycloalkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkinylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)arylene residue, or an unsubstituted or substituted C.sub.2-C.sub.20-alk(hetero)arylene residue; and R.sup.b at each occurrence independently from each other is an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)alkyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkenyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkinyl residue, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)cycloalkyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkenyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkinyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)aromatic residue, or an unsubstituted or substituted C.sub.2-C.sub.20-alk(hetero)aromatic residue, wherein the phosphorous is bound to Cu, and wherein said copper (I) complex has a neutral net charge.

2. The copper (I) complex of claim 1, wherein each X is iodine.

3. The copper (I) complex of claim 1, wherein each ligand L is a monovalent ligand of the same kind.

4. The copper (I) complex of claim 1, wherein each L is independently from each other a diarylphosphine residue of Formula (A2):
P(Ar).sub.m(CHR2-CHR1-CO—Y—R13).sub.n  (A2), wherein: R13 is —R.sup.a—R.sup.b, —R.sup.b—CO—O—R.sup.b, —R.sup.b—O—CO—R.sup.b, —R.sup.b—O—R.sup.b, —R.sup.c—CO—NH—R.sup.b, —R.sup.c—NH—CO—R.sup.b, —R.sup.c—NH—R.sup.b, —R.sup.c—CO—R.sup.b, di- or polyethylene glycol, di- or polypropylene glycol, a polymeric moiety, or a solid support; and R.sup.c at each occurrence independently from another is an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)alkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkinylene residue, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)cycloalkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkinylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)arylene residue, or an unsubstituted or substituted C.sub.2-C.sub.20-alk(hetero)arylene residue, P, Ar, R1, R2, Y, R.sup.a, R.sup.b, m and n are defined as in claim 1, and wherein the phosphorous is bound to Cu.

5. The copper (I) complex of claim 1, wherein each L is a diphenylphosphine residue of Formula (A4): ##STR00063## wherein P, R1, R2, Y, R13, R.sup.a, R.sup.b and R.sup.c are defined as in claim 1, and wherein: R3 to R12 are independently from each other selected from hydrogen, a C.sub.1-C.sub.18-alkyl residue and a C.sub.1-C.sub.12-alkoxy residue, and wherein the phosphorous is bound to Cu.

6. The copper (I) complex of claim 1, wherein two ligands L are interconnected with another, thereby forming a bivalent ligand.

7. The copper (I) complex of claim 1, wherein two L are interconnected with another, thereby forming a bivalent ligand of Formula (A3): ##STR00064## wherein: o and o′ are the same or different and are independently from each other an integer from 0 to 2; p and p′ are the same or different and are independently from each other an integer from 0 to 2; the sum of o and p is 2 and the sum of o′ and p′ is 2; R1 and R1′ are the same or different and are independently from each other selected from hydrogen, —R.sup.a—R.sup.b, —R.sup.a—CO—O—R.sup.b, —R.sup.a—O—CO—R.sup.b, —R.sup.a—O—R.sup.b, —R.sup.a—CO—NH—R.sup.b, —R.sup.a—NH—CO—R.sup.b, —R.sup.a—NH—R.sup.b, and —R.sup.a—CO—R.sup.b; R2 and R2′ are the same or different and are independently from each other selected from hydrogen, —R.sup.a—R.sup.b, —R.sup.a—CO—O—R.sup.b, —R.sup.a—O—CO—R.sup.b, —R.sup.a—O—R.sup.b, —R.sup.a—CO—NH—R.sup.b, —R.sup.a—NH—CO—R.sup.b, —R.sup.a—NH—R.sup.b, and —R.sup.a—CO—R.sup.b; Y and Y′ are the same or different and are independently from each other selected from O and a single bond to a carbon atom of residue Rx; R14 is a bivalent linker comprising 1 to 30 carbon atoms; R15 is —R.sup.a—R.sup.b, —R.sup.c—CO—O—R.sup.b, —R.sup.c—O—CO—R.sup.b, —R.sup.c—O—R.sup.b, —R.sup.c—CO—NH—R.sup.b, —R.sup.c—NH—CO—R.sup.b, —R.sup.c—NH—R.sup.b, —R.sup.c—CO—R.sup.b, di- or polyethylene glycol, di- or polypropylene glycol, a polymeric moiety, or a solid support; P, Ar, R.sup.a, R.sup.b and R.sup.c are defined as in claim 1, wherein phosphorous is each bound to a Cu.

8. The copper (I) complex of claim 1, wherein two L are interconnected with another, thereby forming a bivalent ligand of Formula (A5): ##STR00065## wherein: R3 to R12 and R3′ to R12′ are independently from each other selected from hydrogen, a C.sub.1-C.sub.18-alkyl residue, and a C.sub.1-C.sub.12-alkoxy residue; and R14 is selected from —R.sup.c—, —R.sup.a—O—R.sup.a—, a di- or polyethylene glycol linker, a di- or polypropylene glycol linker, —R.sup.c—CO—O—R.sup.c—, —R.sup.c—CO—O—R.sup.c—O—CO—R.sup.c—, —R.sup.c—O—CO—R.sup.c—, —R.sup.c—O—CO—R.sup.c—CO—O—R.sup.a—, —R.sup.c—CO—NH—R.sup.c—, —R.sup.c—CO—NH—R.sup.c—NH—CO—R.sup.c—, —R.sub.c—NH—CO—R.sup.c—, —R.sup.c—NH—CO—R.sup.c—CO—NH—R.sup.c—, —R.sup.c—NH—R.sup.c—, —R.sup.c—CO—R.sup.c—, and —R.sup.c—NH—R.sup.c—NH—R.sup.c—; R.sup.c at each occurrence independently from another is an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)alkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkinylene residue, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)cycloalkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkinylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)arylene residue, or an unsubstituted or substituted C.sub.2-C.sub.20-alk(hetero)arylene residue; and P, R1, R1′, R2, R2′ Y, Y′, R14, R.sup.a and R.sup.b are defined as in claim 1, wherein phosphorous is each bound to a Cu.

9. The copper (I) complex of claim 1, wherein at least one mono- or bivalent ligand L is selected from the swam consisting of: ##STR00066## wherein the phosphorous is bound to Cu.

10. The copper (I) complex of claim 1, wherein said copper (I) complex is selected from the group consisting of: ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## wherein Ph is an unsubstituted phenyl residue.

11. A method for generating a copper (I) complex of claim 1, said method comprising the following steps: (i) providing, in an inert atmosphere: (a) copper (I) halide, (b) an electronically neutral substituted ligand L as defined in claim 1, and (c) a solvent in which components (a) and (b) are dissolved; (ii) incubating the composition of step (i) at conditions allowing the formation of the copper (I) complex; (iii) optionally removing the solvent and obtaining a solid residue; and (iv) optionally mixing the composition of step (ii) or a solution obtained by dissolving the solid residue of step (iii) with an anti-solvent, thereby forming a precipitate, and subsequently drying the precipitate.

12. A method for generating a copper (I) complex of claim 1, said method comprising the following steps: (i) providing, in an inert atmosphere: (a′) copper (I) halide, (b′) educts of the ligand L: (b1′) an electronically neutral phosphine ligand precursor of formula (L1):
PH(Ar).sub.o(CHR2-CHR1-CO—Y-Rx).sub.p  (L1), wherein: o is an integer from 0 to 2; and p is an integer from 0 to 2; the sum of o and p is 2, and P, H, Ar, R1, R2, Y and Rx are defined as in claim 1; and (b2′) an unbound (meth)acrylate derivative AD compound; (c′) a solvent in which components (a′), (b1′) and (b2′) are dissolved; (ii) incubating the composition of step (i) at conditions allowing the formation of the copper (I) complex; (iii) optionally removing the solvent and obtaining a solid residue; and (iv) optionally mixing the composition of step (ii) or a solution obtained by dissolving the solid residue of step (iii) with an anti-solvent, thereby forming a precipitate, and subsequently drying the precipitate.

13. A method for generating a copper (I) complex of claim 1, said method comprising the following steps: (i) providing, in an inert atmosphere: (a″) a copper (I) complex precursor of Formula (A′) ##STR00075## wherein: each Cu is copper (I); each X is independently from another halogen, each L is independently from each other a ligand of formula (L1):
PH(Ar).sub.o(CHR2-CHR1-CO—Y-Rx).sub.p  (L1), wherein: o is an integer from 0 to 2; and p is an integer from 0 to 2; the sum of o and p is 2, and P, H, Ar, R1, R2, Y and Rx are defined as in claim 1; and wherein said copper (I) complex has a neutral net charge, (b″) an unbound (meth)acrylate derivative AD compound, and (c″) a solvent in which components (a″) and (b″) are dissolved; (ii) incubating the composition of step (i) at conditions allowing the formation of the copper (I) complex; (iii) optionally removing the solvent and obtaining a solid residue; and (iv) optionally mixing the composition of step (ii) or a solution obtained by dissolving the solid residue of step (iii) with an anti-solvent, thereby forming a precipitate, and subsequently drying the precipitate.

14. The method of claim 12, wherein the (meth)acrylate derivative AD compound is a compound of Formula (B): ##STR00076## wherein: R1 is hydrogen, —R.sup.a—R.sup.b, —O—R.sup.b, —R.sup.a—CO—O—R.sup.b, —R.sup.a—O—CO—R.sup.b, —R.sup.a—O—R.sup.b, —R.sup.a—CO—NH—R.sup.b, —R.sup.a—NH—CO—R.sup.b, —R.sup.a—NH—R.sup.b, —R.sup.a—CO—R.sup.b, deuterium, or halogen; R2 is hydrogen, —O—R.sup.b, —R.sup.a—R.sup.b, —R.sup.a—CO—O—R.sup.b, —R.sup.a—O—CO—R.sup.b, —R.sup.a—O—R.sup.b, —R.sup.a—CO—NH—R.sup.b, —R.sup.a—NH—CO—R.sup.b, —R.sup.a—NH—R.sup.b, or —R.sup.a—CO—R.sup.b, deuterium, or halogen; Y is O, NH or a bond to a carbon atom of residue Rx or is N bound to two independent Rx; Rx is a residue comprising from 1 to 30 carbon atoms, a polymeric moiety, or a solid support, wherein Rx may optionally be or contribute to a linker that interconnects two ligands L with another; R.sup.a at each occurrence independently from each other is a single bond, at each occurrence independently from another is an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)alkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkinylene residue, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)cycloalkylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkenylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkinylene residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)arylene residue, or an unsubstituted or substituted C.sub.2-C.sub.20-alk(hetero)arylene residue; and R.sup.b at each occurrence independently from each other is an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)alkyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkenyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)alkinyl residue, an unsubstituted or substituted C.sub.1-C.sub.20-(hetero)cycloalkyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkenyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)cycloalkinyl residue, an unsubstituted or substituted C.sub.2-C.sub.20-(hetero)aromatic residue, or an unsubstituted or substituted C.sub.2-C.sub.20-alk(hetero)aromatic residue.

15. An opto-electronic device containing a copper (I) complex of claim 1.

16. (canceled)

17. The copper (I) complex of claim 1, wherein Y is O or a bond to a carbon atom of residue Rx.

18. The method of claim 14, wherein Y is O or a bond to a carbon atom of residue Rx.

Description

BRIEF DESCRIPTION OF THE FIGURES

[0209] FIG. 1 shows the three-dimensional structure of a copper (I) complex of the present invention: Example Complex 2.

[0210] FIG. 2 shows the three-dimensional structure of a copper (I) complex of the present invention: Example Complex 3.

[0211] FIG. 3 shows the three-dimensional structure of a copper (I) complex of the present invention: Example Complex 23.

[0212] FIG. 4 shows the three-dimensional structure of a copper (I) complex of the present invention: Example Complex 33.

EXAMPLES

[0213] Synthesis of the Copper (I) Complexes of the Present Invention:

[0214] Process A)

[0215] Copper(I) Iodide, phosphine and dry toluene* were placed in a flame-dried Schlenck tube under argon. The solution was heated at 110° C. during 24 hours. Then the mixture was cooled down to the room temperature and the solvent was removed under vacuum. The solid residue was dissolve in dichloromethane (CH.sub.2Cl.sub.2) and the solution was poured into diethyl ether (Et.sub.2O). The complex precipitates directly and was filtrate and washed several times with Et.sub.2O. The product was dried under vacuum. * Other solvents can be used (Dichloromethane or THF) depending of the solubility of phosphines

[0216] Process B)

[0217] Copper(I) Iodide, diphenylphosphine, acrylate derivative and dry toluene were placed in a flame-dried Schlenck tube under argon. The solution was heated at 110° C. during 24 hours. Then the mixture was cooled down to the room temperature and the solvent was removed under vacuum. The solid residue was dissolve in CH2Cl.sub.2 and the solution was poured into Et.sub.2O. The complex precipitates directly and was filtrate and washed several times with Et.sub.2O and hexane. The product was dried under vacuum.

[0218] Process C)

[0219] CuI-diphenylphosphine complex was dissolved in dry acetonitrile (or CH2Cl2) and placed in a flame-dried Schlenck tube under argon. The acrylate derivative was added and the solution was heated at 70° C. during 7 hours. Then the mixture was cooldown to the room temperature and the solvent was removed under vacuum. The solid residue was dissolve in CH.sub.2Cl.sub.2 and the solution was poured into Et.sub.2O. The complex precipitates directly and was filtrate and washed several times with Et2O and hexane. The product was dried under vacuum.

[0220] Process D)

[0221] CuI-diphenylphosphine complex was dissolved in dry dichloromethane and placed in a flame-dried Schlenck tube under argon. The acrylate derivative was added and the solution was exposed to UV light using an light-emitting diode (LED) at, for example, 365 nm during 6 hours. Then the mixture was cooled down to the room temperature and the solvent was removed under vacuum. The solid residue was dissolve in CH2Cl2 and the solution was poured into Et.sub.2O or Hexane. The complex precipitates directly and was filtrate and washed several times with Et.sub.2O and hexane. The product was dried under vacuum.

[0222] The following ligands were used:

TABLE-US-00001 TABLE 1 Ligands Ligand Olefin precursor (short name) State PPh2H Powder Ligand 2 acrolein Powder Ligand 3 isopentyl diacrylate Powder Ligand 4 propanediol diacrylate Powder Ligand 5 hexanediol diacrylate Powder Ligand 6 ethanediol dimetacrylate Powder Ligand 7 hexanediol dimetacrylate Powder Ligand 8 ditertbutylphenol acrylate Powder Ligand 9 methyl itaconate Powder Ligand 10 3-pentadecylphenyl acrylate Oil Ligand 11 3,4,5-tris(dodecyloxy)benzyl Oil acrylate Ligand 12 ortho-allyl-phenol acrylate Oil Ligand 13 Hex-1-yne acrylate Oil Ligand 14 Hydroxypivalyl hydroxypivalate Oil bis[6-(acryloyloxy)hexanoate] Ligand 15 Cyclohexyl metacrylate Oil Ligand 16 Furane metacrylate Oil Ligand 17 Ethylhexyl acrylate Oil Ligand 18 Perfluoroaryl acrylate Oil Ligand 19 4,6-di-ter-butylbenzene-1,3 diol Oil diacrylate Ligand 20 Tertiobutyl metacrylate Powder Ligand 21 Butyl acrylate Oil Ligand 22 Butyl metacrylate Oil Ligand 23 Ethyl acrylate Powder Ligand 24 Ethyl metacrylate Powder Ligand 29 PEG-9 acrylate Oil Ligand 30 Hexyl 1,6 diethylene glycol Powder acrylate Ligand 31 Thiophene acrylate Powder Ligand 32 Methyl acrylate

TABLE-US-00002 TABLE 2 Copper (I) complexes prepared with the corresponding ligands (monochelating as Cu.sub.4I.sub.4(RPPh.sub.2).sub.4 and bis chelating as Cu4I4(Ph.sub.2PRPPh.sub.2).sub.2) ID Phosphine used Coordination Procedure used state Complex 1 PPh2H mono A powder Complex 2 Ligand 2 mono A, B, C, D powder Complex 3 Ligand 3 bis A powder Complex 4 Ligand 4 bis A powder Complex 5 Ligand 5 bis A powder Complex 6 Ligand 6 bis A powder Complex 7 Ligand 7 bis A powder Complex 8 Ligand 8 mono A powder Complex 9 Ligand 9 mono A powder Complex 10 Ligand 10 mono A oil Complex 11 Ligand 11 mono A oil Complex 12 Ligand 12 mono A oil Complex 13 Ligand 13 mono A oil Complex 14 Ligand 14 bis A, D oil Complex 15 Ligand 15 mono A, B, C oil Complex 16 Ligand 16 mono A oil Complex 17 Ligand 17 mono A oil Complex 18 Ligand 18 mono A oil Complex 19 Ligand 19 mono A oil Complex 20 Ligand 20 mono A Powder Complex 21 Ligand 21 mono A, D oil Complex 22 Ligand 22 mono A oil Complex 23 Ligand 23 mono A, D Powder Complex 24 Ligand 24 mono A Powder Complex 25 Ligand 21 + mono A oil Ligand 23 Complex 26 Ligand 15 + mono A oil Ligand 16 Complex 27 Ligand 12 + mono A oil Ligand 17 Complex 28 Ligand 12 + mono A oil Ligand 13 Complex 29 Ligand 29 mono A oil Complex 30 Ligand 30 bis A, D Powder Complex 31 Ligand 31 mono A Powder Complex 32 Ligand 12 A Ligand 32

[0223] The chemical structures of several copper (I) complexes are depicted as follows:

##STR00029##

[0224] .sup.1H NMR (500 MHz, CDCl.sub.3): 5.82 (d, J=315.6 Hz, 4H), 7.18 (m, 16H), 7.26 (m, 8H), 7.49 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 128.57 (d, J=9 Hz), 129.59, 130.32 (d, J=29 Hz), 134.1 (d, J=12.4 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −39 (br) ppm. Anal. Calcd for C.sub.64H.sub.68Cu.sub.4I.sub.4O.sub.4P.sub.4: C, 38.26; H, 2.94. Found: C, 36.49; H, 2.82. IR (neat) v=2975, 1476, 1437, 1089, 887, 819, 725, 686 cm.sup.−1 ATG: 5% par mass lost at 257° C.

##STR00030##

[0225] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.60-7.50 (m, 16H), 7.39-7.32 (m, 8H), 7.31-7.25 (m, 16H), 2.69-2.56 (m, 8H), 2.51-2.51 (m, 8H), 1.91 (s, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 173.17; 133.65 (d); 133.24 (d); 129.76; 128.68 (d); 38.75 (d); 29.80 (d, J=8 Hz); 22.19 ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29.53 (br) ppm. Anal. Calcd for C.sub.64H.sub.68Cu.sub.4I.sub.4O.sub.4P.sub.4: C, 43.02; H, 3.84. Found: C, 43.61; H, 3.92. IR (neat) v=3053, 2912, 1710, 1575, 1487, 1434, 1356, 1215, 1159, 1099, 868, 739, 693 cm-.sup.1. ATG: 5% per mass lost at 317° C.

##STR00031##

[0226] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.63-7.54 (m, 16H), 7.43-7.36 (m, 8H), 7.34-7.27 (m, 16H), 3.91 (s, 8H), 2.69-2.53 (m, 16H), 0.91 (s, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 207.57; 133.65 (d); 133.24; 132.92; 129.76; 128.68 (d); 72.36; 35.09, 38.98 (d); 30.21; 20.95 (d) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −31.75 (br) ppm. Anal. Calcd for C.sub.71H.sub.80Cu.sub.4I.sub.4O.sub.8P.sub.4: C, 43,80; H, 4,14. Found: C, 44.63; H, 4,1. ATG: 5% per mass lost at 253° C.

##STR00032##

[0227] .sup.1H NMR 6 (500 MHz, CDCl.sub.3): δ 7.70-7.10 (m, 40H), 4.20 (br, 8H), 3.51 (br, 2H), 2.69-2.53 (br, 16H), 1.92 (br, 4H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): 173.05 (d); 133.00 (d); 132.72; 129,62; 128.49 (br); 64.33; 29.50; 27.67; 22.59 ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −31.82 (br) ppm.

##STR00033##

[0228] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.83-7.12 (m, 40H), 4.11-3.63 (br, 8H), 3.51 (br 2H), 3.51 (br 2H), 2.74 (br, 2H), 2.23 (br, 2H), 0.90 (br, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 173.32; 133.48 (d, J=13 Hz); 132.86 (d, J=25 Hz); 129.81; 128.59 (d, J=10 Hz); 64.74, 38.98 (d, J=9 Hz); 28.70; 26.46; 22.75 (d, J=21 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30.52 (br) ppm.

##STR00034##

[0229] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.83-7.12 (m, 40H), 4.11-3.63 (br, 8H), 3.51 (br 2H), 3.51 (br 2H), 2.74 (br, 2H), 2.23 (br, 2H), 0.90 (br, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 207.57; 133.65 (d); 133.24; 132.92; 129.76; 128.68 (d); 72.36; 35.09, 38.98 (d); 30.21; 20.95 (d) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −31.75 (br) ppm.

##STR00035##

[0230] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.83-7.12 (m, 40H), 4.11-3.63 (br, 8H), 3.51 (br 2H), 3.51 (br 2H, CH*), 2.74 (br, 2H, CH.sub.2—P), 2.23 (br, 2H, CH.sub.2—P), 0.90 (br, 12H, CH.sub.3) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 176.52; 134.18 (m); 133.12 (m); 129.70 (m); 128.5; 64.55, 36.67; 31.57 (m); 28.78; 26.96; 26.38, 20.12 (m) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30.18 (br) ppm.

##STR00036##

[0231] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.83-7.12 (m, 16H), 7.40-7.29 (m, 28H), 7.16 (dd, 4H), 6.77 (d, 4H), 2.86 (br, 8H), 2.74 (br, 8H), 1.27 (s, 36H), 1.19 (br, 36H) ppm. .sup.13C NMR 126 MHz, CDCl.sub.3): δ 170.62 (d); 146.92; 145.73; 138.88; 132.51 (d); 131.59; 128.82; 127.62; 123.002; 122.73; 122.153; 114.904; 33.62; 33.57; 30.48; 29.34; 28.66; 21.18 (br). .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29.80 (br) ppm.

##STR00037##

[0232] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.65-7.50 (m, 16H), 7.40-7.25 (m, 24H), 3.38 (s, 24H), 3.29 (br, 4H), 2.90-2.70 (m, 4H), 2.65-2.45 (m, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 174.31 (d); 171.87; 133.56 (m); 132.39 (d), 129.89 (dd); 128.59 (d); 52.19; 51.64; 37.86 (d); 36.59 (d); 28.22 (d) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −28.66 (br) ppm. IR (neat) v=3033, 2946, 1730, 1579, 1487, 1477, 1436, 1366, 1191, 1099, 1011, 795, 688 cm.sup.−1

##STR00038##

[0233] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.70-7.57 (br, 16H), 7.37-7.27 (m, 24H), 7.20-7.14 (m, 4H), 7.00-6.95 (d, 4H), 6.79-6.72 (m, 8H) 2.90-2.74 (br, 8H), 2.73-2.63 (br, 8H), 2.52 (t, 8H), 1.54 (br, 8H), 1.25 (s, 96H), 0.86 (t, 12H) ppm .sup.13C NMR (126 MHz, CDCl.sub.3): δ 171.61 (d); 152.87; 144.66 (m); 133.49 (d), 132.89 (dd); 128.59 (d); 125.86, 124.49, 118.82, 36.01; 32.15; 31.43; 29.90; 29.82; 29.73; 29.58; 22.88; 14.28 ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29.76 (br) ppm.

##STR00039##

[0234] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.63-7.47 (br, 16H), 7.34-7.20 (m, 24H), 6.48 (s, 8H, .sub.1), 3.90 (br, 24H), 2.73-2.63 (br, 16H), 1.80-1.66 (br, 24H), 1.44 (br, 24H), 1.27 (s, 192H), 0.88 (t, 36H) ppm .sup.13C NMR (126 MHz, CDCl.sub.3): δ 171.75; 152.15; 137.08; 132.29 (d); 129.66; 128.72; 127.62 (d); 105.92; 72.39; 68.09; 65.85; 30.94; 29.91; 29.36; 28.76; 28.73; 28.67; 28.47; 28.38; 25.15; 21.70; 13.12 ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30.20 (br) ppm.

##STR00040##

[0235] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 2.63 (m, 8H), 2.77 (m, 8H), 3.05 (d, 8H), 4.84 (m, 8H), 5.68 (m, 4H), 6.80 (m, 4H), 7.06 (m, 12H), 7.26 (m, 24H), 7.55 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 23.12 (d, J=17.3 Hz), 29.65 (d, J=8 Hz), 34.57, 116.26, 122.37, 126.02, 127.30, 128.53 (d, J=9 Hz), 129.82, 130.28, 131.85, 132.62 (d, J=29 Hz), 133.28 (d, J=12.0 Hz)), 135.77, 148.91 171.34 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ: −30 (br) ppm. IR (neat) v=3070, 2985, 2910, 1751-1579, 1487, 1429, 1346, 1215, 1123, 912, 730, 686 cm.sup.−1

##STR00041##

[0236] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 1.53 (m, 8H), 1.66 (m, 8H), 1.94 (m, 4H), 2.17 (td, J=7.3 Hz, 8H), 2.57 (m, 16H), 4.01 (t, 8H), 7.32 (m, 24H), 7.60 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 18.08, 22.29 (d, J=17.3 Hz), 24.84, 27.55, 29.44 (d, J=8 Hz), 64.16, 68.81, 83.94, 128.79 (d, J=9 Hz), 129.67, 132.78 (d, J=29 Hz), 133.40 (d, J=12.0 Hz)), 173.03 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30 (br) ppm. IR (neat) v=3291, 3056, 2948, 1725, 1479,1429, 1344, 1220, 1169, 1094, 735, 684 cm.sup.−1

##STR00042##

[0237] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −31 (br) ppm

[0238] IR (neat) v=3055, 2951, 1730, 1475, 1429, 1218, 1147, 1031, 730, 693.cm.sup.−1

##STR00043##

[0239] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.70 (m, 8H), 7.65 (m, 8H), 7.31 (m, 24H), 4.44 (m, 4H), 2.96 (m, 8H), 2.80 (m, 8H), 2.31 (m, 4H), 1.72 (m, 8H), 1.51 (m, 8H), 1.27 (m, 16H), 1.15 (d, .sup.1J=7.0 Hz, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 18.76 (d, J=7 Hz), 23.56 (d, J=Hz), 25.39, 30.44 (d, J=15.5 Hz), 31.31 (d, J=6 Hz)), 36.35 (d, J=7.0 Hz), 72.57, 128.30 (t), 129.27 (d), 133.02 (d, J=12.6 Hz)), 134.24 (d, J=13.5 Hz)), 175.45 (d, J=9 Hz)) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30 (br) ppm. IR (neat) v=3069, 2928, 2855, 1722, 1450, 1430, 1194, 1153, 1012, 912, 740, 695 cm.sup.−1

##STR00044##

[0240] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 7.69 (m, 8H), 7.58 (m, 8H), 7.33 (m, 24H), 3.97 (m, 12H), 3.76 (m, 8H), 2.99 (m, 4H), 2.81 (m, 4H), 2.36 (m, 4H), 1.85 (m, 12H), 1.51 (m, 4H), 1.22 (d, .sup.1J=7.0 Hz, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 18.61 (d, J=7 Hz), 25.72 (d, J=9 Hz), 28.01 (d, J=4 Hz), 36.17 (d, J=7.7 Hz), 64.41 (d, J=11 Hz), 68.4 (d, J=7 Hz), 76.25 (d, 4 Hz), 128.48 (t), 129.27 (d), 133.02 (d, J=12.6 Hz)), 134.24 (d, J=13.5 Hz)), 175.45 (d, J=9 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30 (br) ppm. IR (neat) v=3065, 2970, 2861, 1715, 1480, 1446, 1429, 1164, 1111, 1016, 819, 737, 686 cm.sup.−1

##STR00045##

[0241] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 0.8 (m, 24H), 1.31 (m, 32H), 1.51 (m, 4H), 2.57 (m, 16H), 3.91 (dd, 8H), 7.33 (m, 24H), 7.60 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 9.95, 13.05, 21.30 (d, J=17.3 Hz), 21.94, 22.67, 28.96, 29.32 (d, J=8), 30.45, 37.67, 66.24, 127.76 (d, J=9 Hz), 128.59, 130.05 (d, J=28 Hz), 132.35 (d, J=12.1 Hz),), 1723.23 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30 (br) ppm. IR (neat) v=3054, 2958, 2864, 1730, 1456, 1431, 1378,1344, 1220, 1162, 1096, 737, 689 cm.sup.−1

##STR00046##

[0242] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 2.69 (m, 8H), 2.90 (m, 8H), 7.34 (m, 24H), 7.61 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 22.90 (d, J=17.3 Hz), 30.13 (d, J=8 Hz, 128.71 (d, J=9 Hz), 129.61, 130 (d), 132.85 (d, J=28 Hz), 133.38 (d, J=12.1 Hz), 139 (d), 134 (d), 142 (d), 169.32 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30 (br) ppm. IR (neat) v=2975, 2902, 1781, 1516, 1429, 1094, 1038, 987, 735, 688 cm.sup.−1

##STR00047##

[0243] .sup.1H NMR (300 MHz, CDCl.sub.3): δH=1.27 (s, 36H), 2.40 (m, 8H), 2.55 (m, 8H), 6.89 (s, 2H), 7.29 (m, 26H), 7.38 (m, 16H)

[0244] .sup.13C {1H} NMR (75 MHz, CDCl3): δ C=22.91 (d), 30.25, 31.49 (d) 34.65, 119.10, 125.55, 128.61 (d), 128.94, 132.83 (d), 137.60 (d), 146.69, 171.50 (d)

[0245] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −30.3

[0246] IR (neat) v=2956, 2900, 1754, 1480, 1479, 1434, 1354, 1210, 1099, 917, 735, 694 cm-1

##STR00048##

[0247] .sup.1H NMR (500 MHz, CDCl.sub.3) δ: 7.51 (m, 16H, C.sub.6H.sub.4), 7.28 (m, 24H, C.sub.6H.sub.4), 2.30 (m, 8H), 1.94 (m, 4H), 1.29 (s, 36H), 1.15 (d, 12H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 18.60, 27.96, 32.69, 37.91, 80.36, 128.45 (d, J=9 Hz), 129.65, 132.86 (d(d, J=29 Hz)), 133.20 (d, J=12.2 Hz)), 175.52 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −28 (br) ppm. IR (neat) v=3054, 2973, 1726, 1462, 1431, 1363, 1343, 1140, 1023, 846, 737, 696 cm.sup.−1

##STR00049##

[0248] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 0.85 (t, 12H), 1.29 (m, 8H), 1.55 (m, 8H), 2.55 (m, 16H), 3.96 (t, 8H), 7.31 (m, 24H), 7.60 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 13.74, 19.15, 20.02 (d, J=17.3 Hz), 26.94, 30.66 (d, J=8 Hz), 64.58, 128.52 (d, J=9 Hz), 129.73, 132.81 (d, J=29 Hz), 134.78 (d, J=12.0 Hz)), 173.34 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29 (br) ppm. IR (neat) v=3057, 2993, 2871, 1729, 1459, 1431, 1156, 1016, 734, 696 cm.sup.−1

##STR00050##

[0249] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 0.85 (t, 12H), 1.22 (d, 12H), 1.26 (m, 8H), 1.55 (m, 8H), 2.01 (m, 4H), 2.55 (m, 8H), 3.92 (m, 8H), 7.28 (m, 24H), 7.59 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 13.78, 18.67, 19.27, 30.68, 32.77, 37.16, 64.43, 128.48 (d, J=9 Hz), 129.75, 132.80 (d, J=29 Hz), 134.01 (d, J=12.0 Hz)), 176.15 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −30 (br) ppm. IR (neat) v=3065, 2954, 1732, 1475, 1434, 1344, 1218, 1165, 1066, 738, 686 cm.sup.−1

##STR00051##

[0250] .sup.1H NMR (500 MHz, CDCl.sub.3): δH=1.15 (t, 12H), 2.52 (m, 16H), 4.01 (m, 8H), 7.28 (m, 24H), 7.57 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 14.19, 22.39 (d, J=17.3 Hz), 29.5 (d, J=8 Hz), 60.59, 128.54 (d, J=9 Hz), 129.61, 132.85 (d, J=28 Hz), 133.38 (d, J=12.1 Hz),), 173.23 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29.69 ppm. IR (neat) v=3056, 2969, 2872, 1727, 1476, 1430, 1369, 1348, 1226, 1163, 1097, 1024, 733, 691 cm.sup.−1. Anal. Calcd for C.sub.64H.sub.68Cu.sub.4I.sub.4O.sub.4P.sub.4: C, 43,83; H, 4.02. Found: C, 41.76; H, 4.38. ATG: 5% lost of mass at 253° C. DSC: Pf: 128° C. recristallization at 61° C.

##STR00052##

[0251] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 1.1 (t, 12H), 1.23 (d, 12H), 2.1 (m, 4H), 2.41 (m, 8H), 3.97 (m, 8H), 7.28 (m, 24H), 7.50 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 14.22, 18.74, 32.70, 37.27 60.60, 128.50 (d, J=9 Hz), 129.69, 132.86 (d, J=28 Hz), 133.45 (d, J=12.2 Hz), 176.14 (d, J=17.2 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29 (br) ppm. IR (neat) v=3065, 2978, 2932, 1730, 1456, 1438, 1369, 1175, 1153, 1096, 1020, 732, 693 cm.sup.−1

##STR00053##

[0252] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −30 (br)

##STR00054##

[0253] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −29 (br)

##STR00055##

[0254] .sup.1H NMR (600 MHz, CDCl.sub.3): δH=0.94 (m, 12H), 1.23 (m, 16H), 1.51 (m, 2H), 2.56 (m, 8H), 2.72 (m, 4H), 2.85 (m, 4H), 3.16 (d, 4H), 3.90 (m, 4H), 4.93 (m, 4H), 5.77 (m, 2H), 6.94 (m, 2H), 7.19 (m, 6H), 7.34 (m, 24H), 7.63 (m, 16H)

[0255] .sup.13C {1H} NMR (75 MHz, CDCl3): δ C=10.93, 14.09, 22.21 (d), 22.34 (d), 22.96, 23.68, 28.87, 29.54 (d), 29.60 (d), 30.29, 34.56, 38.60, 67.29, 116.26, 122.37, 126.03, 127.29, 128.43 (d), 128.60 (d), 129.68, 129.81, 130.29, 131.87, 132.41, 132.62, 133.29 (d), 133.39 (d), 135.77, 148.93, 171.28 (d), 173.1 (d)

[0256] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −29.9 (br)

##STR00056##

[0257] .sup.1H NMR (600 MHz, CDCl.sub.3): δH=1.53 (m, 4H), 1.69 (m, 4H), 1.96 (br, 2H), 2.17 (td, 4H), 2.58 (m, 8H), 2.70 (m, 4H), 2.86 (m, 4H), 3.11 (d, 4H), 4.01 (t, 4H), 4.92 (m, 4H), 5.77 (m, 2H), 6.94 (m, 2H), 7.19 (m, 6H), 7.34 (m, 24H), 7.63 (m, 16H)

[0258] .sup.13C {1H} NMR (75 MHz, CDCl3): δ C=18.10, 22.24 (d), 22.41 (d), 24.83, 27.53, 29.46 (d), 29.63 (d), 31.61, 34.57, 64.15, 84.18, 116.24, 122.37, 126.04, 127.30, 128.45 (d), 128.61 (d), 129.71, 129.82, 130.30, 131.87, 132.42 (d), 132.70 (d), 133.30 (d), 133.40, 135.76, 148.93, 171.28 (d), 172.98 (d).

[0259] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −29.68 (br)

##STR00057##

[0260] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 2.50 (m, 16H), 2.37 (m, 8H), 3.32 (s, 12H), 3.49 (m, 8H), 3.59 (m, 112H), 4.12 (t, 8H), 7.28 (m, 24H), 7.54 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 22.27 (d, J=17 Hz), 29.33 (d, J=9 Hz), 59.04, 63.79, 68.7, 70.58, 71.95, 128.49 (d, J=9 Hz), 129.68, 132.73 (d, J=28 Hz), 133.40 (d, J=12.1 Hz), 172.92 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29.92 (br) ppm. IR (neat) v=3056, 2874, 1729, 1433, 1343, 1270, 1219, 1097, 951, 849, 730, 698 cm.sup.−1

##STR00058##

[0261] .sup.1H NMR (500 MHz, CDCl.sub.3) δ: 7.60 (m, 16H), 7.32 (m, 24H), 4.14 (m, 4H), 3.97 (m, 4H), 3.63 (m, 12H), 3.42 (m, 4H), 2.58 (m, 16H), 1.49 (m, 8H), 1.28 (m, 8H).

[0262] .sup.31P NMR (202 MHz, CDCl.sub.3) δ: −30.21 (br)

[0263] .sup.13C NMR (75 MHz, CDCl.sub.3): δ 21.64 (d), 24.96, 27.36, 30.58 (d), 63.46, 69.57, 69.71, 127.50 (d), 128.69, 131.80 (d) 132.33 (d), 172.10 (d)

##STR00059##

[0264] .sup.1H NMR (500 MHz, CDCl.sub.3): δ 2.60 (m, 16H), 5.18 (s, 8H), 6.93 (dd, J=5.93 Hz, 4H), 7.04 (d, J=3.4 Hz, 4H), 7.25 (dd, J=5.1 Hz, 4H), 7.29 (m, 24H), 7.58 (m, 16H) ppm. .sup.13C NMR (126 MHz, CDCl.sub.3): δ 22.23 (d, J=17 Hz), 29.51 (d, J=9 Hz), 60.73, 126.94 (d, J=6.1 Hz), 128.35, 128.54 (d, J=9 Hz), 129.7, 132.85 (d, J=28 Hz), 133.48 (d, J=12.1 Hz), 137.82, 172.82 (d, J=17 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): δ −29.78 (br) ppm. IR (neat) v=3064, 2937, 1729, 1481, 1435, 1335, 1263, 1219, 1158, 944, 852, 735 cm-1

##STR00060##

[0265] .sup.1H NMR (600 MHz, CDCl.sub.3): δH=1.94 (s, 6H), 2.50 (m, 4H), 2.63 (m, 8H), 2.80 (m, 4H), 3.19 (d, 4H), 4.98 (m, 4H), 5.80 (m, 2H), 6.91 (m, 2H), 7.16 (m, 6H), 7.29 (m, 24H), 7.58 (m, 16H)

[0266] .sup.13C {1H} NMR (75 MHz, CDCl3): δ C=21.36 (d), 22.71, 29.57 (d), 31.64, 34.81, 38.71 (d), 116.32, 122.39, 126.10, 127.34, 128.70 (d), 128.90 (d), 129.87, 129.98, 130.34, 131.87, 132.14 (d), 132.65 (d), 133.05 (d), 133.15, 135.87, 148.94, 171.27 (d), 207.30 (d).

[0267] .sup.31P NMR (161 MHz, CDCl.sub.3) δ: −30 (br)

[0268] Determining the Structure:

[0269] The three-dimensional (3D) (crystal) structure was determined by means of NMR. The results are depicted in FIGS. 1 to 4.

[0270] For Complex 2, the following distances and angles have been determined. The numbers correspond to those depicted in FIG. 1.

TABLE-US-00003 TABLE 3 Distances in the CuI cubane-like core structure of Complex 2: No. Objects Length 1 Cu1 P1  2.245(2) 2 Cu1 I1 2.7368(9) 3 Cu1 I4 2.7041(9) 4 Cu1 I3 2.7413(9) 5 Cu1 Cu4 2.7413(9) 6 Cu1 Cu3 2.7413(9) 7 Cu1 Cu2 2.7413(9) 8 Cu2 I1 2.7413(9) 9 Cu2 P2 2.7413(9) 10 Cu2 I2 2.7413(9) 11 Cu2 Cu4 2.7413(9) 12 Cu2 Cu3 2.7413(9) 13 Cu2 I4 2.7413(9) 14 Cu3 I1 2.7413(9) 15 Cu3 I2 2.7413(9) 16 Cu3 P3 2.7413(9) 17 Cu3 I3 2.7413(9) 18 Cu3 Cu4 2.7413(9) 19 Cu4 I3 2.7413(9) 20 Cu4 P4 2.7413(9) 21 Cu4 I2 2.7413(9) 22 2.7413(9) 2.7413(9) 2.7413(9)

TABLE-US-00004 TABLE 4 Angles determined for the CuI cubane-like core structure of Complex 2: No. compared objects Angle 1 Cu1 Cu2 Cu3  58.53(3) 2 Cu1 Cu2 Cu4  56.85(3) 3 Cu1 Cu2 I1  59.68(3) 4 Cu1 Cu2 I2 104.44(3) 5 Cu1 Cu2 I4  59.30(3) 6 Cu1 Cu3 Cu2  60.51(3) 7 Cu1 Cu3 Cu4  59.20(3) 8 Cu1 Cu3 I1  61.02(3) 9 Cu1 Cu3 I2 107.07(4) 10 Cu1 Cu3 I3  58.02(3) 11 Cu1 Cu4 Cu2  59.82(3) 12 Cu1 Cu4 Cu3  60.35(3) 13 Cu1 Cu4 I2 108.21(4) 14 Cu1 Cu4 I3  58.41(3) 15 Cu1 Cu4 I4  59.57(3) 16 Cu1 I1 Cu2  61.62(3) 17 Cu1 I1 Cu3  60.88(3) 18 Cu1 I3 Cu3  61.51(3) 19 Cu1 I3 Cu4  60.75(3) 20 Cu1 I4 Cu2  62.49(3) 21 Cu1 I4 Cu4  59.48(3) 22 Cu2 Cu1 Cu3  60.96(3) 23 Cu2 Cu1 Cu4  63.33(3) 24 Cu2 Cu1 I1  58.70(3) 25 Cu2 Cu1 I3 112.67(4) 26 Cu2 Cu1 I4  58.22(3) 27 Cu2 Cu3 Cu4  62.75(3) 28 Cu2 Cu3 I1  59.44(3) 29 Cu2 Cu3 I2  59.31(3) 30 Cu2 Cu3 I3 110.21(4) 31 Cu2 Cu4 Cu3  59.74(3) 32 Cu2 Cu4 I2  58.33(3) 33 Cu2 Cu4 I3 107.86(3) 34 Cu2 Cu4 I4  56.69(3) 35 Cu2 I1 Cu3  62.95(3) 36 Cu2 I2 Cu3  62.72(3) 37 Cu2 I2 Cu4  64.87(3) 38 Cu2 I4 Cu4  64.34(3) 39 Cu3 Cu1 Cu4  60.45(3) 40 Cu3 Cu1 I1  58.10(3) 41 Cu3 Cu1 I3  60.47(3) 42 Cu3 Cu1 I4 108.38(4) 43 Cu3 Cu2 Cu4  57.51(3) 44 Cu3 Cu2 I1  57.61(3) 45 Cu3 Cu2 I2  57.96(3) 46 Cu3 Cu2 I4 107.27(3) 47 Cu3 Cu4 I2  59.29(3) 48 Cu3 Cu4 I3  59.65(3) 49 Cu3 Cu4 I4 107.23(3) 50 Cu3 I2 Cu4  61.68(3) 51 Cu3 I3 Cu4  60.76(3) 52 Cu4 Cu1 I1 109.35(4) 53 Cu4 Cu1 I3  60.84(3) 54 Cu4 Cu1 I4  60.94(3) 55 Cu4 Cu2 I1 104.97(3) 56 Cu4 Cu2 I2  56.79(3) 57 Cu4 Cu2 I4  58.97(3) 58 Cu4 Cu3 I1 110.73(4) 59 Cu4 Cu3 I2  59.03(3) 60 Cu4 Cu3 I3  59.58(3) 61 I1 Cu1 I3 110.42(3) 62 I1 Cu1 I4 111.38(3) 63 I1 Cu2 I2 110.18(3) 64 I1 Cu2 I4 113.23(3) 65 I1 Cu3 I2 113.04(3) 66 I1 Cu3 I3 110.81(3) 67 I2 Cu2 I4 108.61(3) 68 I2 Cu3 I3 113.20(3) 69 I2 Cu4 I3 113.50(3) 70 I2 Cu4 I4 107.96(3) 71 I3 Cu1 I4 116.15(3) 72 I3 Cu4 I4 112.74(3) 73 P1 Cu1 Cu2 133.30(6) 74 P1 Cu1 Cu3 144.58(6) 75 P1 Cu1 Cu4 151.48(6) 76 P1 Cu1 I1  98.82(5) 77 P1 Cu1 I3 113.60(6) 78 P1 Cu1 I4 105.04(6) 79 P2 Cu2 Cu1 155.09(6) 80 P2 Cu2 Cu3 138.16(6) 81 P2 Cu2 Cu4 143.70(6) 82 P2 Cu2 I1 109.77(6) 83 P2 Cu2 I2 100.41(5) 84 P2 Cu2 I4 113.87(6) 85 P3 Cu3 Cu1 148.56(6) 86 P3 Cu3 Cu2 144.90(6) 87 P3 Cu3 Cu4 138.77(6) 88 P3 Cu3 I1 110.50(6) 89 P3 Cu3 I2 103.98(6) 90 P3 Cu3 I3 104.76(6) 91 P4 Cu4 Cu1 140.22(6) 92 P4 Cu4 Cu2 146.30(6) 93 P4 Cu4 Cu3 147.38(6) 94 P4 Cu4 I2 111.54(6) 95 P4 Cu4 I3 105.48(6) 96 P4 Cu4 I4 105.34(6)

TABLE-US-00005 TABLE 5 Angles determined for the copper (1) complex structure of Complex 2: No. Compared Objects Angle 1 C1 C2 H2 118.6 2 C1 C2 C3 122.8(8) 3 C1 C6 C5 121.3(9) 4 C1 C6 H6 119.4 5 C1 P1 C7 104.4(3) 6 C1 P1 C13 108.9(4) 7 C1 P1 Cu1 113.2(3) 8 C10 C11 H11 119.8 9 C10 C11 C12 120.6(8) 10 C11 C12 H12 119.7 11 C12 C7 P1 122.5(5) 12 C13 C14 H14A 109.0 13 C13 C14 H14B 109.1 14 C13 C14 C15 113.1(7) 15 C13 P1 Cu1 108.4(3) 16 C14 C13 P1 119.1(6) 17 C14 C15 C16 115.9(7) 18 C14 C15 O1 121.2(8) 19 C15 C16 H16A 109.6 20 C15 C16 H16B 109.5 21 C15 C16 H16C 109.5 22 C16 C15 O1 122.7(8) 23 C17 C18 H18 119.6 24 C17 C18 C19 121.0(7) 25 C17 C22 C21 120.5(7) 26 C17 C22 H22 119.7 27 C17 P2 C23 105.7(3) 28 C17 P2 C29 102.0(3) 29 C17 P2 Cu2 117.8(2) 30 C18 C17 C22 118.1(6) 31 C18 C17 P2 118.5(5) 32 C18 C19 H19 120.4 33 C18 C19 C20 119.2(8) 34 C19 C20 H20 119.3 35 C19 C20 C21 121.2(8) 36 C2 C1 C6 118.2(8) 37 C2 C1 P1 118.5(6) 38 C2 C3 H3 122 39 C2 C3 C4 116.7(9) 40 C20 C21 H21 120.0 41 C20 C21 C22 120.0(8) 42 C21 C22 H22 119.8 43 C22 C17 P2 123.1(5) 44 C23 C24 H24 119.9 45 C23 C24 C25 120.1(8) 46 C23 C28 C27 120.6(8) 47 C23 C28 H28 119.8 48 C23 P2 C29 103.1(3) 49 C23 P2 Cu2 113.2(2) 50 C24 C23 C28 118.7(7) 51 C24 C23 P2 120.3(6) 52 C24 C25 H25 120 53 C24 C25 C26 120(1)   54 C25 C26 H26 120 55 C25 C26 C27 120(1)   56 C26 C27 H27 120 57 C26 C27 C28 120(1)   58 C27 C28 H28 119.7 59 C28 C23 P2 120.6(6) 60 C29 C30 H30A 109.6 61 C29 C30 H30B 109.6 62 C29 C30 C31 110.4(6) 63 C29 P2 Cu2 113.5(2) 64 C3 C4 H4 119 65 C3 C4 C5 122(1)   66 C30 C29 P2 113.0(5) 67 C30 C31 C32 118.1(7) 68 C30 C31 O2 120.6(8) 69 C31 C32 H32A 109.4 70 C31 C32 H32B 109.4 71 C31 C32 H32C 109.5 72 C32 C31 O2 121.3(8) 73 C33 C34 H34 120.2 74 C33 C34 C35 119.7(8) 75 C33 C38 C37 120.5(8) 76 C33 C38 H38 119.7 77 C33 P3 C39 104.8(3) 78 C33 P3 C45 106.2(3) 79 C33 P3 Cu3 116.3(2) 80 C34 C33 C38 118.8(7) 81 C34 C33 P3 117.6(6) 82 C34 C35 H35 119.4 83 C34 C35 C36 121.2(9) 84 C35 C36 H36 120 85 C35 C36 C37 120(1)   86 C36 C37 H37 120 87 C36 C37 C38 120(1)   88 C37 C38 H38 119.8 89 C38 C33 P3 123.6(6) 90 C39 C40 H40 120.2 91 C39 C40 C41 119.7(7) 92 C39 C44 C43 119.8(6) 93 C39 C44 H44 120.1 94 C39 P3 C45 102.6(3) 95 C39 P3 Cu3 112.2(2) 96 C4 C5 H5 120 97 C4 C5 C6 119(1)   98 C40 C39 C44 119.5(6) 99 C40 C39 P3 123.3(5) 100 C40 C41 H41 119.8 101 C40 C41 C42 120.4(8) 102 C41 C42 H42 119.9 103 C41 C42 C43 120.3(8) 104 C42 C43 H43 119.9 105 C42 C43 C44 120.2(8) 106 C43 C44 H44 120.2 107 C44 C39 P3 117.1(5) 108 C45 C46 H46A 108.8 109 C45 C46 H46B 108.8 110 C45 C46 C47 113.9(7) 111 C45 P3 Cu3 113.5(2) 112 C46 C45 P3 113.5(5) 113 C46 C47 C48 118.6(8) 114 C46 C47 O3 121.4(8) 115 C47 C48 H48A 110 116 C47 C48 H48B 110 117 C47 C48 H48C 110 118 C48 C47 O3 120.0(9) 119 C49 C50 H50 119.0 120 C49 C50 C51 121.9(8) 121 C49 C54 C53 120.9(7) 122 C49 C54 H54 119.5 123 C49 P4 C55 104.6(3) 124 C49 P4 C61 104.5(3) 125 C49 P4 Cu4 116.0(2) 126 C5 C6 H6 119 127 C50 C49 C54 117.3(7) 128 C50 C49 P4 120.1(5) 129 C50 C51 H51 120.3 130 C50 C51 C52 119.6(8) 131 C51 C52 H52 120.4 132 C51 C52 C53 119.3(8) 133 C52 C53 H53 119.5 134 C52 C53 C54 121.1(8) 135 C53 C54 H54 119.6 136 C54 C49 P4 122.6(5) 137 C55 C56 H56 119.9 138 C55 C56 C57 120.2(8) 139 C55 C60 C59 121.6(7) 140 C55 C60 H60 119.2 141 C55 P4 C61 100.5(3) 142 C55 P4 Cu4 113.2(2) 143 C56 C55 C60 118.0(6) 144 C56 C55 P4 123.1(5) 145 C56 C57 H57 119.2 146 C56 C57 C58 121.4(8) 147 C57 C58 H58 120.3 148 C57 C58 C59 119.3(8) 149 C58 C59 H59 120.2 150 C58 C59 C60 119.5(7) 151 C59 C60 H60 119.1 152 C6 C1 P1 122.9(6) 153 C60 C55 P4 118.9(5) 154 C61 C62 H62A 109.0 155 C61 C62 H62B 108.9 156 C61 C62 C63 112.6(6) 157 C61 P4 Cu4 116.2(2) 158 C62 C61 P4 114.8(5) 159 C62 C63 C64 117.1(7) 160 C62 C63 O4 121.0(7) 161 C63 C64 H64A 109.5 162 C63 C64 H64B 109.5 163 C63 C64 H64C 109.5 164 C64 C63 O4 121.9(8) 165 C7 C8 H8 119.4 166 C7 C8 C9 121.5(6) 167 C7 C12 C11 120.7(7) 168 C7 C12 H12 119.6 169 C7 P1 C13 103.9(3) 170 C7 P1 Cu1 117.4(2) 171 C8 C7 C12 117.8(6) 172 C8 C7 P1 119.7(5) 173 C8 C9 H9 119.8 174 C8 C9 C10 120.2(7) 175 C9 C10 H10 120.3 176 C9 C10 C11 119.2(8) 177 Cu1 Cu2 Cu3 58.53(3) 178 Cu1 Cu2 Cu4 56.85(3) 179 Cu1 Cu2 I1 59.68(3) 180 Cu1 Cu2 I2 104.44(3) 181 Cu1 Cu2 I4 59.30(3) 182 Cu1 Cu3 Cu2 60.51(3) 183 Cu1 Cu3 Cu4 59.20(3) 184 Cu1 Cu3 I1 61.02(3) 185 Cu1 Cu3 I2 107.07(4) 186 Cu1 Cu3 I3 58.02(3) 187 Cu1 Cu4 Cu2 59.82(3) 188 Cu1 Cu4 Cu3 60.35(3) 189 Cu1 Cu4 I2 108.21(4) 190 Cu1 Cu4 I3 58.41(3) 191 Cu1 Cu4 I4 59.57(3) 192 Cu1 I1 Cu2 61.62(3) 193 Cu1 I1 Cu3 60.88(3) 194 Cu1 I3 Cu3 61.51(3) 195 Cu1 I3 Cu4 60.75(3) 196 Cu1 I4 Cu2 62.49(3) 197 Cu1 I4 Cu4 59.48(3) 198 Cu2 Cu1 Cu3 60.96(3) 199 Cu2 Cu1 Cu4 63.33(3) 200 Cu2 Cu1 I1 58.70(3) 201 Cu2 Cu1 I3 112.67(4) 202 Cu2 Cu1 I4 58.22(3) 203 Cu2 Cu3 Cu4 62.75(3) 204 Cu2 Cu3 I1 59.44(3) 205 Cu2 Cu3 I2 59.31(3) 206 Cu2 Cu3 I3 110.21(4) 207 Cu2 Cu4 Cu3 59.74(3) 208 Cu2 Cu4 I2 58.33(3) 209 Cu2 Cu4 I3 107.86(3) 210 Cu2 Cu4 I4 56.69(3) 211 Cu2 I1 Cu3 62.95(3) 212 Cu2 I2 Cu3 62.72(3) 213 Cu2 I2 Cu4 64.87(3) 214 Cu2 I4 Cu4 64.34(3) 215 Cu3 Cu1 Cu4 60.45(3) 216 Cu3 Cu1 I1 58.10(3) 217 Cu3 Cu1 I3 60.47(3) 218 Cu3 Cu1 I4 108.38(4) 219 Cu3 Cu2 Cu4 57.51(3) 220 Cu3 Cu2 I1 57.61(3) 221 Cu3 Cu2 I2 57.96(3) 222 Cu3 Cu2 I4 107.27(3) 223 Cu3 Cu4 I2 59.29(3) 224 Cu3 Cu4 I3 59.65(3) 225 Cu3 Cu4 I4 107.23(3) 226 Cu3 I2 Cu4 61.68(3) 227 Cu3 I3 Cu4 60.76(3) 228 Cu4 Cu1 I1 109.35(4) 229 Cu4 Cu1 I3 60.84(3) 230 Cu4 Cu1 I4 60.94(3) 231 Cu4 Cu2 I1 104.97(3) 232 Cu4 Cu2 I2 56.79(3) 233 Cu4 Cu2 I4 58.97(3) 234 Cu4 Cu3 I1 110.73(4) 235 Cu4 Cu3 I2 59.03(3) 236 Cu4 Cu3 I3 59.58(3) 237 H10 C10 C11 120.4 238 H11 C11 C12 119.7 239 H13A C13 H13B 107.2 240 H13A C13 C14 107.5 241 H13A C13 P1 107.6 242 H13B C13 C14 107.4 243 H13B C13 P1 107.5 244 H14A C14 H14B 107.6 245 H14A C14 C15 108.9 246 H14B C14 C15 108.9 247 H16A C16 H16B 109.5 248 H16A C16 H16C 109.4 249 H16B C16 H16C 109.4 250 H18 C18 C19 119.5 251 H19 C19 C20 120.4 252 H2 C2 C3 118.6 253 H20 C20 C21 119.5 254 H21 C21 C22 120.1 255 H24 C24 C25 120.0 256 H25 C25 C26 120 257 H26 C26 C27 120 258 H27 C27 C28 120 259 H29A C29 H29B 107.9 260 H29A C29 C30 108.9 261 H29A C29 P2 109.0 262 H29B C29 C30 108.9 263 H29B C29 P2 109.0 264 H3 C3 C4 122 265 H30A C30 H30B 108.1 266 H30A C30 C31 109.5 267 H30B C30 C31 109.6 268 H32A C32 H32B 109 269 H32A C32 H32C 110 270 H32B C32 H32C 110 271 H34 C34 C35 120.1 272 H35 C35 C36 119 273 H36 C36 C37 120 274 H37 C37 C38 120 275 H4 C4 C5 119 276 H40 C40 C41 120.2 277 H41 C41 C42 119.7 278 H42 C42 C43 119.8 279 H43 C43 C44 119.9 280 H45A C45 H45B 107.8 281 H45A C45 C46 108.8 282 H45A C45 P3 108.8 283 H45B C45 C46 109.0 284 H45B C45 P3 108.9 285 H46A C46 H46B 107.6 286 H46A C46 C47 108.8 287 H46B C46 C47 108.8 288 H48A C48 H48B 109 289 H48A C48 H48C 109 290 H48B C48 H48C 109 291 H5 C5 C6 120 292 H50 C50 C51 119.1 293 H51 C51 C52 120.1 294 H52 C52 C53 120.3 295 H53 C53 C54 119.4 296 H56 C56 C57 119.9 297 H57 C57 C58 119.3 298 H58 C58 C59 120.4 299 H59 C59 C60 120.3 300 H61A C61 H61B 107.7 301 H61A C61 C62 108.5 302 H61A C61 P4 108.7 303 H61B C61 C62 108.5 304 H61B C61 P4 108.6 305 H62A C62 H62B 108.0 306 H62A C62 C63 109.1 307 H62B C62 C63 109.1 308 H64A C64 H64B 110 309 H64A C64 H64C 110 310 H64B C64 H64C 109 311 H8 C8 C9 119.1 312 H9 C9 C10 119.9 313 I1 Cu1 I3 110.42(3) 314 I1 Cu1 I4 111.38(3) 315 I1 Cu2 I2 110.18(3) 316 I1 Cu2 I4 113.23(3) 317 I1 Cu3 I2 113.04(3) 318 I1 Cu3 I3 110.81(3) 319 I2 Cu2 I4 108.61(3) 320 I2 Cu3 I3 113.20(3) 321 I2 Cu4 I3 113.50(3) 322 I2 Cu4 I4 107.96(3) 323 I3 Cu1 I4 116.15(3) 324 I3 Cu4 I4 112.74(3) 325 P1 Cu1 Cu2 133.30(6) 326 P1 Cu1 Cu3 144.58(6) 327 P1 Cu1 Cu4 151.48(6) 328 P1 Cu1 I1 98.82(5) 329 P1 Cu1 I3 113.60(6) 330 P1 Cu1 I4 105.04(6) 331 P2 Cu2 Cu1 155.09(6) 332 P2 Cu2 Cu3 138.16(6) 333 P2 Cu2 Cu4 143.70(6) 334 P2 Cu2 I1 109.77(6) 335 P2 Cu2 I2 100.41(5) 336 P2 Cu2 I4 113.87(6) 337 P3 Cu3 Cu1 148.56(6) 338 P3 Cu3 Cu2 144.90(6) 339 P3 Cu3 Cu4 138.77(6) 340 P3 Cu3 I1 110.50(6) 341 P3 Cu3 I2 103.98(6) 342 P3 Cu3 I3 104.76(6) 343 P4 Cu4 Cu1 140.22(6) 344 P4 Cu4 Cu2 146.30(6) 345 P4 Cu4 Cu3 147.38(6) 346 P4 Cu4 I2 111.54(6) 347 P4 Cu4 I3 105.48(6) 348 P4 Cu4 I4 105.34(6)

[0271] The molecular structure of the other Complexes was found to be similar.

[0272] The photochemical (optical) properties were investigated, in particular the emission and excitation maxima and the quantum yields:

TABLE-US-00006 TABLE 6 Emission and excitation wavelengths of the cubanes and quantum yields (determined in dry state (i.e., without solvent). ID Emission max (nm) Excitation max (nm) Quantum yield Complex 1 570 340 17% Complex 2 606 344 74% Complex 3 514 364 70% Complex 4 568 310 67% Complex 5 563 310 76% Complex 6 571 320 56% Complex 7 566 310 47% Complex 8 563 310 85% Complex 9 557 330 49% Complex 10 591 320 25% Complex 11 576 330 11% Complex 12 563 300 62% Complex 13 570 310 40% Complex 14 565 310 30% Complex 15 569 300 61% Complex 16 566 320 50% Complex 17 604 310 15% Complex 18 580 333 18% Complex 19 566 320 61% Complex 20 566 300 18% Complex 21 569 310 60% Complex 22 569 310 24% Complex 23 560 320 99% Complex 24 589 310 22% Complex 25 572 310 27% Complex 26 572 310 45% Complex 27 575 320 46% Complex 28 575 310 51% Complex 29 570 320  6% Complex 30 560 330 52% Complex 31 570 320 38%

[0273] It was seen that the copper (I) complexes show an absorption maximum in the UV range and an emission maximum in the visible range.

##STR00061##

[0274] .sup.1H NMR (500 MHz, CDCl.sub.3): δH=1.19 (t, J=7.1 Hz, 24H), 2.33-2.72 (m, 32H), 4.05 (q, J=7.2 Hz, 16H), 7.41 (m, 12H), 7.80 (m, 8H) ppm.

[0275] .sup.13C NMR (126 MHz, CDCl.sub.3): δ 14.17, 22.02 (d, J=15.5 Hz), 29.53 (d, J=4.7 Hz), 60.66, 128.85 (d, J=8.5 Hz), 130.40, 133.16, 133.18, 172.72 (d, J=15 Hz) ppm. .sup.31P {.sup.1H} NMR (203 MHz, CDCl.sub.3): 0-35.28 ppm.

[0276] Complex 33 was found to have an excitation maximum of 360 nm and a quantum yield of 96%.

[0277] It was found that also ligands that have more than one aliphatic substituents to the phosphorous atoms in accordance with the present invention can very well be used in the context of the present invention, in particular as light-emitting compounds