NON-LINEAR DIELECTRIC MATERIALS AND CAPACITOR

Abstract

A composite organic compound characterized by polarizability and resistivity that has a general structural formula: where C is a chromophore fragment, P is an optionally connected rylene fragment, D and A are electron donating and accepting groups respectively, and R represents resistive substituents optionally connected directly or via dopant connecting groups.

Claims

1. A composite organic compound characterized by polarizability and resistivity that has a general structural formula: where C is a chromophore fragment comprises an aromatic substituent independently selected from the group consisting of six-membered aromatic rings, five-membered heteroaromatic rings, fused ring systems containing at least one six-membered aromatic ring, and fused ring systems containing at least one five-membered heteroaromatic ring having one heteroatom selected from the group consisting of O, N, S and Se, wherein C has the general structure: wherein each Q comprises an aromatic substituent independently selected from the group consisting of six-membered aromatic rings, five-membered heteroaromatic rings, fused ring systems of at least one six-membered aromatic ring, and fused ring systems of at least one five-membered heteroaromatic ring having one heteroatom selected from the group consisting of O, N, S and Se, B comprises a conjugated functional group, the value of i for each B is an integer between zero and three, inclusively, and j is from one to nine, inclusive; and R, D, A, and B may independently be attached to a member of a heteroaromatic ring alpha to a heteroatom, and when Q is an aromatic ring, B is attached to a member of said aromatic ring para to R or another B, and where D and A can independently be ortho, meta, or para to B on Q. D comprises an electron donating group capable of releasing electrons into said conjugated aromatic system; l is an integer between zero and three, inclusively, A comprises an electron accepting group capable of pulling electrons from said conjugated aromatic system; m is an integer between zero and three, inclusively, R is selected from the group consisting of straight-chained or branched alkyl, alkoxy, alkylthio, alkylamino, and fluoro-alkyl group containing from one to thirty carbon atoms attached to said composite organic compound wherein R may independently be attached to C and P by an alkyl moiety or connecting group, k is the number of R groups attached to the composite organic compound wherein R may independently be attached to C and P by an alkyl moiety or a connecting group, the value of k is an integer between 0 and 15, inclusively, S comprises a heteroaromatic substituent selected from the group consisting of five-membered heteroaromatic rings having one heteroatom selected from the group consisting of O, N, S and Se, fused ring systems containing at least one five-membered heteroaromatic ring having one heteroatom selected from the group consisting of O, S and Se, fused ring systems containing at least one five-membered heteroaromatic ring having two to four N heteroatoms, fused ring systems containing all five-membered heteroaromatic rings having one heteroatom selected from the group consisting of O, N, S and Se, pyrimidine and purine, so that S is tricyanovinylated at a ring position alpha to a heteroatom; where P is a polycyclic conjugated molecular fragments having two-dimensional flat form and self-assembling by pi-pi stacking in a column-like supramolecule, n is the number of the polycyclic conjugated molecular fragments which is equal to 0, 2, or 4.

2. The composite organic compound of claim 1 wherein the chromophore further comprises more than one electron donor-conjugated bridge-electron acceptor combination in series or in parallel.

3. The composite organic compound of claim 1 wherein the chromophore (C) further comprises more than one electron donor-conjugated bridge-electron acceptor combination in series and in parallel.

4. The composite organic compound of claim 1 wherein the conjugated bridge (B) is selected from the group consisting of alkenes, dienes, trienes, polyenes, 1,2-diphenylethene, 1,2-diphenyldiazene, styrene, hexa-1,3,5-trienylbenzene, 1,4-di(thiophen-2-yl)buta-1,3-diene and combinations thereof.

5. The composite organic compound of claim 1 wherein the electron donor (D) is selected from the group consisting of —O.sup.− (phenoxides, like —ONa or —OK), —NH.sub.2, —NHR, —NR.sub.2, —OH, —OR (ethers), —NHCOR (amides, from amine side), —OCOR (esters, from alcohol side), alkyls, —C.sub.6H.sub.5, vinyls, wherein R is radical selected from the list comprising alkyl (methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, cyclohexyl etc.), allyl (—CH2-CH═CH2), benzyl (—CH2C6H5) groups, phenyl (+substituted phenyl) and other aryl (aromatic) groups and combinations thereof.

6. The composite organic compound of claim 1 wherein the electron acceptor (A) is selected from the group consisting of —NO.sub.2, —NH.sub.3.sup.+ and —NR.sub.3.sup.+ (quaternary nitrogen salts), counterion Cl.sup.− or Br.sup.−, —CHO (aldehyde), —CRO (keto group), —SO.sub.3H (sulfonic acids), —SO.sub.3R (sulfonates), —SO.sub.2NH.sub.2 (sulfonamides), —COOH (carboxylic acid), —COOR (esters, from carboxylic acid side), —COCl (carboxylic acid chlorides), —CONH.sub.2 (amides, from carboxylic acid side), —CF.sub.3, —CCl.sub.3, —CN, wherein R is radical selected from the list comprising alkyl (methyl, ethyl, iso-propyl, tent-butyl, neo-pentyl, cyclohexyl etc.), allyl (—CH.sub.2—CH═CH.sub.2), benzyl (—CH.sub.2C.sub.6H.sub.5) groups, phenyl (+substituted phenyl) and other aryl (aromatic) groups and combinations thereof

7. The composite organic compound of claim 1 wherein the electron donor is an amino group, the electron acceptor is selected from the group consisting of nitro, carbonyl and cyano groups and the conjugated bridge is selected from the group consisting of alkenes, diphenyldiazene, 1,2-diphenylethene and combinations thereof.

8. The composite organic compound of claim 1 wherein the electron donor (D) and electron acceptor (A) groups are arranged on the chromophore fragment such that the fragment is non-centrosymmetric.

9. The composite organic compound of claim 1 wherein the polycyclic organic molecule fragment (P) is comprised of rylene fragments meeting the formula ##STR00036## wherein n=1-10, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 independently are selected from the group consisting of hydrogen atom, double bonded oxygen, and groups joining with R.sub.1 and R.sub.2 to form polycyclic heterocycles structures, R1 and R2 are independently selected from the group consisting of aryl, heteroaryl, or groups joining with R.sub.3, R.sub.4, R.sub.5, and R.sub.6 to form polycyclic heterocycles.

10. The composite organic compound of claim 1 wherein the polycyclic organic molecule fragment (P) is comprised of rylene fragments selected from structures 1 to 21: ##STR00037## ##STR00038## ##STR00039##

11. The composite organic compound of claim 1, wherein the connecting groups on R are independently selected from a single bond and the list comprising the following structures: 29-39, where W is hydrogen (H) or an alkyl group: ##STR00040##

12. A metadielectric layer comprising of one or more of the type of composite organic compound as in claim 1, wherein the nonliearly polarizable fragments comprising a chromophore molecule with at least two dopant groups, the resistive dielectric envelope formed by resistive substituents providing solubility of the organic compound in a solvent and electrically insulating the column-like supramolecules from each other, and wherein the metadielectric layer's relative permittivity is greater than or equal to 1000 and resistivity is greater than or equal to 10.sup.16 Ohm cm.

13. The metadielectric layer according to claim 12, wherein the column-like supramolecules are formed by the polycyclic conjugated molecule comprising rylene fragments of same and different length.

14. A meta-capacitor comprising two metal electrodes positioned parallel to each other and which can be rolled or flat and planar and metadielectric layer between said electrodes, wherein the layer comprises the polarizable compound according to claim 1, wherein the nonlinearly polarizable fragments comprising chromophore molecule with at least one dopant group are placed into the resistive dielectric envelope formed by resistive substituents providing solubility of the organic compound in a solvent and electrically insulating the column-like supramolecules from each other.

15. A capacitor comprising: a first electrode, a second electrode, and a metadielectric film as in claim 15.

16. The capacitor of claim 15 wherein the metadielectric film comprises of composite organic compound according to claim 1, and which demonstrates a non-linear effect.

17. The capacitor of claim 15 wherein the dielectric film comprises a polycyclic conjugated molecule fragment that exhibits pi-pi stacking.

18. A multilayer capacitor comprising a plurality of layers wherein each layer comprises a metadielectric film of any combination of the composite organic compounds according to claim 1 between a first electrode and a second electrode.

Description

BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING

[0027] FIG. 1 shows a composite organic compound comprising a chromophore, two dopant groups and two resistive tails.

[0028] FIG. 2A shows a capacitor with two electrodes and a dielectric according to an aspect of the present disclosure.

[0029] FIG. 2B shows a coiled film capacitor according to an aspect of the present disclosure.

SUMMARY

[0030] According to an aspect of the present disclosure, a composite organic compound characterized by polarizability and resistivity has a general structural formula: [0031] C is a chromophore fragment comprising an aromatic substituent independently selected from the group consisting of six-membered aromatic rings, five-membered heteroaromatic rings, fused ring systems containing at least one six-membered aromatic ring, and fused ring systems containing at least one five-membered heteroaromatic ring having one heteroatom selected from the group consisting of O, N, S and Se, [0032] C has the general structure: [0033] each Q comprises an aromatic substituent independently selected from the group consisting of six-membered aromatic rings, five-membered heteroaromatic rings, fused ring systems of at least one six-membered aromatic ring, and fused ring systems of at least one five-membered heteroaromatic ring having one heteroatom selected from the group consisting of O, N, S and Se, [0034] B comprises a conjugated functional group, the value of i for each B is an integer between zero and three, inclusively, and j is from one to nine, inclusive; and [0035] R, D, A, and B may independently be attached to a member of a heteroaromatic ring alpha to a heteroatom, and when Q is an aromatic ring, B is attached to a member of said aromatic ring para to R or another B, and [0036] D and A can independently be ortho, meta, or para to B on Q. [0037] D comprises an electron donating group capable of releasing electrons into said conjugated aromatic system; l is an integer between zero and three, inclusively, [0038] A comprises an electron accepting group capable of pulling electrons from said conjugated aromatic system; m is an integer between zero and three, inclusively,

[0039] R is selected from the group consisting of straight-chained or branched alkyl, alkoxy, alkylthio, alkylamino, and fluoro-alkyl group containing from one to thirty carbon atoms attached to said composite organic compound wherein R may independently be attached to C and P by an alkyl moiety or connecting group, k is the number of R groups attached to the composite organic compound wherein R may independently be attached to C and P by an alkyl moiety or a connecting group, the value of k is an integer between 0 and 15, inclusively, [0040] S comprises a heteroaromatic substituent selected from the group consisting of five-membered heteroaromatic rings having one heteroatom selected from the group consisting of O, N, S and Se, fused ring systems containing at least one five-membered heteroaromatic ring having one heteroatom selected from the group consisting of O, S and Se, fused ring systems containing at least one five-membered heteroaromatic ring having two to four N heteroatoms, fused ring systems containing all five-membered heteroaromatic rings having one heteroatom selected from the group consisting of O, N, S and Se, pyrimidine and purine, so that S is tricyanovinylated at a ring position alpha to a heteroatom;

[0041] P is a polycyclic conjugated molecular fragments having two-dimensional flat form and self-assembling by pi-pi stacking in a column-like supramolecule, n is the number of the polycyclic conjugated molecular fragments which is equal to 0, 2, or 4.

[0042] Another aspect of the present disclosure is to provide a capacitor with a high power output. A further aspect of the present disclosure is to provide a capacitor featuring a high dielectric constant sustainable to high frequencies. A still further aspect of the present disclosure is to provide a capacitor featuring voltage dependent capacitance. In yet another aspect of the present disclosure, a method to make such a capacitor is provided.

[0043] The capacitor, in its simplest form, comprises a first electrode, a second electrode and a composite chromophore, comprising ordered resistive tails and dopant groups, between the first electrode and the second electrode. The dopant groups on the composite chromophore can be electron acceptor and/or electron donor groups separated by a conjugated bridge. The conjugated bridge comprises one or more double bonds that alternate with single bonds in an unsaturated compound. Among the many elements that may be present in the double bond, carbon, nitrogen, oxygen and sulfur are the most preferred heteroatoms. The π electrons in the conjugated bridge are delocalized across the length of the bridge. Among the many types of ordered resistive tails that may be present in the composite chromophore, alkyl chains, branched alkyl chains, fluorinated alkyl chains, branched flouroalkyl chains, poly(methyl methacrylate) chains are examples and are preferentially positioned on the terminal aromatic rings of a chromophore. When a bias is applied across the first and second electrodes, the composite chromophore becomes more or less polarized with electron density moving from the donor to acceptor or vice versa. When the bias is removed, the original charge distribution is restored. Typically, the capacitor comprises a plurality of composite chromophores as a dielectric film with lamella or micellular structures.

[0044] In one embodiment, a liquid or solid composite chromophore is placed between the first and second electrodes. A solid chromophore is, for example, pressed into a pellet and placed between the first electrode and the second electrode. The chromophore can be ground into a powder before pressing.

[0045] In another embodiment, the composite chromophore is dissolved or suspended in a solvent. Which can be used to spin coat or pulled to form a dielectric film.

[0046] In another embodiment, the tailless composite chromophore is dissolved or suspended in a polymer. This is termed a “guest-host” system where the chromophore is the guest and the polymer is the host. Polymer hosts include, but are not limited to, poly(methyl methacrylate), polyimides, polycarbonates and poly(ε-caprolactone). These systems are cross-linked or non-cross-linked.

[0047] In another embodiment, the tailless composite chromophore is attached to a polymer. This is termed a “side-chain polymer” system. This system has the advantages over guest-host systems because high composite chromophore concentrations are incorporated into the polymer without crystallization, phase separation or concentration gradients. Side chain polymers include, but are not limited to, poly[4-(2,2-dicyanovinyl)-N-bis(hydroxyethyl)aniline-alt-(4,4′-methylenebis(phenylisocyanate))]urethane, poly[4-(2,2-dicyanovinyl)-N-bis(hydroxyethyl)aniline-alt-(isophoronediisocyanate)]urethane, poly(9H-carbazole-9-ethyl acrylate), poly(9H-carbazole-9-ethyl methacrylate), poly(Disperse Orange 3 acrylamide), poly(Disperse Orange 3 methacrylamide), poly(Disperse Red 1 acrylate), poly(Disperse Red 13 acrylate), poly(Disperse Red 1 methacrylate), poly(Disperse Red 13 methacrylate), poly[(Disperse Red 19)-alt-(1,4-diphenylmethane urethane)], poly(Disperse Red 19-p-phenylene diacrylate), poly(Disperse Yellow 7 acrylate), poly(Disperse Yellow 7 methacrylate), poly[(methyl methacrylate)-co-(9-H-carbazole-9-ethyl acrylate)], poly[(methyl methacrylate)-co-(9-H-carbazole-9-ethyl methacrylate)], poly[methyl methacrylate-co-(Disperse Orange 3 acrylamide)], poly[methyl methacrylate-co-(Disperse Orange 3 methacrylamide)], poly[(methyl methacrylate)-co-(Disperse Red 1 acrylate)], poly[(methyl methacrylate)-co-(Disperse Red 1 methacrylate)], poly[(methyl methacrylate)-co-(Disperse Red 13 acrylate)], poly[(methyl methacrylate)-co-(Disperse Red 13 methacrylate)], poly[methyl methacrylate-co-(Disperse Yellow 7 acrylate)], poly[methyl methacrylate-co-(Disperse Yellow 7 methacrylate)], poly [[(S)-1-(4-nitrophenyl)-2-pyrrolidinemethyl]acrylate], poly[((S)-1-(4-nitrophenyl)-2-pyrrolidinemethyl)acrylate-co-methyl methacrylate], poly[((S)-(−)-1-(4-nitrophenyl)-2-pyrrolidinemethyl]methacrylate] and poly[((S)-(−)-1-(4-nitrophenyl)-2-pyrrolidinemethyl)methacrylate-co-methyl methacrylate]. These systems are cross-linked or non-cross-linked. In such embodiments the chromophore may be attached to the polymer directly via a single bond or through linking groups. Such linking groups may include but are not limited to the following.

TABLE-US-00001 TABLE 1 Examples of Suitable Linking Groups Between Polymer and Chromophore. —O— 29 [00001] 30 [00002] 31 [00003] 32 [00004] 33 [00005] 34 [00006] 35 [00007] 36 [00008] 36 [00009] 37 [00010] 38
Where W is hydrogen (H) or an alkyl group.

[0048] In another embodiment, the tailless composite chromophore is incorporated into the polymer backbone. These systems are termed “main-chain polymer” systems. Main-chain polymers include, but are not limited to, 4-methoxy-4′-carbomethoxy-α-amino-α′-cyanostilbenes, the AB copolymer of α-cyano-m-methoxy-p-(ω-oxypropoxy)cinnamate with ω-hydroxydodecanoate, poly[(4-N-ethylene-N-ethylamino)-α-cyanocinnamate, bispheno A-4-amino-4′-nitrotolan, bisphenol A-4-nitroaniline and bisphenol A-N,N-dimethyl-4-nitro-1,2-phenylenediamine. These systems are cross-linked or non-cross-linked.

[0049] In another embodiment, the tailless composite chromophore is embedded in matrices such as oxides, halides, salts and organic glasses. An example of a matrix is inorganic glasses comprising the oxides of aluminum, boron, silicon, titanium, vanadium and zirconium.

[0050] The chromophore is aligned, partially aligned or unaligned. The composite chromophore is preferably aligned as this results in higher capacitance values in the capacitor. The preferred method of alignment is to apply a dc electric field to the composite chromophore at a temperature at which the composite chromophore can be oriented. This method is termed “poling.” Poling is generally performed near the glass transition temperature of polymeric and glassy systems. A preferred method of poling is corona poling.

[0051] A preferred capacitor further does not comprise a first insulator between the first electrode and the composite chromophore nor a second insulator between the second electrode and the composite chromophore.

[0052] Preferred electron donors include, but are not limited to, amino and phosphino groups and combinations thereof. Preferred electron acceptors include, but are not limited to, nitro, carbonyl, oxo, thioxo, sulfonyl, malononitrile, isoxazolone, cyano, dicyano, tricyano, tetracycano, nitrile, dicarbonitrile, tricarbonitrile, thioxodihydropyrimidinedione groups and combinations thereof. More conjugated bridges include, but are not limited to, 1,2-diphenylethene, 1,2-diphenyldiazene, styrene, hexa-1,3,5-trienylbenzene and 1,4-di(thiophen-2-yl)buta-1,3-diene, alkenes, dienes, trienes, polyenes, diazenes and combinations thereof.

[0053] The first and second electrodes are selected from the group consisting of conductors and semiconductors. Conductors include, but are not limited to, metals, conducting polymers, carbon nano-materials, and graphite including graphene sheets. Semiconductors include, but are not limited to, silicon, germanium, silicon carbide, gallium arsenide and selenium. The electrode may or may not be formed on a flat support. Flat supports may include, but are not limited to, glass, plastic, silicon, and metal surfaces.

[0054] FIG. 1 illustrates the components in a chromophore 8, an electron donor 4, a conjugated bridge 3, an electron acceptor 2, and tail 1. A composite chromophore can have more than one electron donor 4, electron acceptor 2, conjugated bridge 3, and tail 1. A composite chromophore can comprise a mixture of molecules.

[0055] In one embodiment of the present disclosure, the metadielectric layer comprises the column-like supramolecules formed by the electro-polarizable compounds comprising rylene fragments of a single or a variety of lengths. Some non-limiting embodiments are shown below.

TABLE-US-00002 TABLE 2 Rylene fragment examples. [00011] 1 [00012] 2 [00013] 3 [00014] 4 [00015] 5 [00016] 6 [00017] 7 [00018] 8 [00019] 9 [00020] 10 [00021] 11 [00022] 12 [00023] 13 [00024] 14 [00025] 15 [00026] 16 [00027] 17 [00028] 18 [00029] 19 [00030] 20 [00031] 21

[0056] In one embodiment of the present disclosure, the layer's relative permittivity is greater than or equal to 1000. In another embodiment of the present disclosure, the polarization (P) of the metadielectric layer comprises first-order (ε.sub.(1)) and second-order (ε.sub.(2)) and third order (ε.sub.(3)) permittivities according to the following formula:

P=ε.sub.0(ε.sub.1−1)E+ε.sub.0ε.sub.2E.sup.2+ε.sub.0ε.sub.3E.sup.3+ . . .

[0057] where P is the polarization of the material, which also can be represented by the following formula:

P=NP.sub.induced

[0058] where P.sub.induced is the induced polarization which can be expressed by the formula:

P.sub.induced=αE.sub.loc+βE.sub.loc.sup.2+γE.sub.loc.sup.3+ . . .

[0059] where E.sub.loc is the localized field and is expressed by the formula:

E.sub.loc=E+P/(3ε.sub.0)

[0060] The real part of the relative permittivity (ε′) as can be seen from the above equations, also comprises first, second, and third order permittivities. Further, permittivity of a capacitor is a function of applied voltage and thickness of the capacitor's dielectric (d). Where voltage is the DC-voltage which is applied to the crystal metadielectric layer, and d is the layer thickness. In another embodiment of the present invention, the layer's resistivity is greater than or equal to 10.sup.13 ohm cm.

[0061] In one embodiment, the composite chromophore comprises more than one electron donor-conjugated bridge-electron acceptor combination in series. In another embodiment, the composite chromophore comprises more than one electron donor-conjugated bridge-electron acceptor combination in parallel. In yet another embodiment, the composite chromophore comprises electron donor-conjugated bridge-electron acceptor combinations both in parallel and in series. In still another embodiment, the composite chromophore comprises a more than one type of ordered resistive tails.

[0062] The present disclosure provides the meta-capacitor comprising two metal electrodes positioned parallel to each other and which can be rolled or flat and planar and a metadielectric layer between said electrodes. The layer comprises the electro-polarizable compounds as disclosed above.

[0063] A metadielectric layer maybe a film comprising the above described composite organic compound comprising chromophore fragments with dopants and ordered resistive tails.

[0064] The meta-capacitor comprises a first electrode 1, a second electrode 2, and a metadielectric layer 3 disposed between said first and second electrodes as shown in FIG. 1A. Electrodes 1 and 2 may be made of a metal, such as copper, zinc, or aluminum or other conductive material such as graphite or carbon nanomaterials and are generally planar in shape.

[0065] Electrodes 1 and 2 may be flat and planar and positioned parallel to each other. Alternatively, the electrodes may be planar and parallel, but not necessarily flat, they may be coiled, rolled, bent, folded, or otherwise shaped to reduce the overall form factor of the capacitor. It is also possible for the electrodes to be non-flat, non-planar, or non-parallel or some combination of two or more of these. By way of example and not by way of limitation, a spacing d between electrodes 1 and 2 may range from about 100 nm to about 100 μm. The maximum voltage V.sub.bd between electrodes 1 and 2 is approximately the product of the breakdown field E.sub.bd and the electrode spacing d. If E.sub.bd=0.1 V/nm and the spacing d between electrodes 1 and 2 is 100 microns (100,000 nm), the maximum voltage V.sub.bd would be 10,000 volts.

[0066] Electrodes 1 and 2 may have the same shape as each other, the same dimensions, and the same area A. By way of example, and not by way of limitation, the area A of each electrode 1 and 2 may range from about 0.01 m.sup.2 to about 1000 m.sup.2. By way of example and not by way of limitation for rolled capacitors, electrodes up to, e.g., 1000 m long and 1 m wide.

[0067] These ranges are non-limiting. Other ranges of the electrode spacing d and area A are within the scope of the aspects of the present disclosure.

[0068] If the spacing d is small compared to the characteristic linear dimensions of electrodes (e.g., length and/or width), the capacitance C of the capacitor may be approximated by the formula:

C=εε.sub.0A/d,   (V)

where ε.sub.o is the permittivity of free space (8.85×10.sup.−12 Coulombs.sup.2/(Newton.Math.meter.sup.2)) and ε is the dielectric constant of the dielectric layer. The energy storage capacity U of the capacitor may be approximated as:

U=½εε.sub.oAE.sub.bd.sup.2d   (VI)

[0069] The energy storage capacity U is determined by the dielectric constant ε, the area A, and the breakdown field E.sub.bd. By appropriate engineering, a capacitor or capacitor bank may be designed to have any desired energy storage capacity U. By way of example, and not by way of limitation, given the above ranges for the dielectric constant ε, electrode area A, and breakdown field E.sub.bd a capacitor in accordance with aspects of the present disclosure may have an energy storage capacity U ranging from about 500 Joules to about 2.Math.10.sup.16 Joules.

[0070] For a dielectric constant ε ranging, e.g., from about 100 to about 1,000,000 and constant breakdown field E.sub.bd between, e.g., about 0.1 and 0.5 V/nm, a capacitor of the type described herein may have a specific energy capacity per unit mass ranging from about 10 W.Math.h/kg up to about 100,000 W.Math.h/kg, though implementations are not so limited.

[0071] The present disclosure includes meta-capacitors that are coiled, e.g., as depicted in FIG. 1B. In this example, a meta-capacitor 20 comprises a first electrode 21, a second electrode 22, and a metadielectric material layer 23 of the type described hereinabove disposed between said first and second electrodes. Electrodes 21 and 22 may be made of a metal, such as copper, zinc, or aluminum or other conductive material such as graphite or carbon nanomaterials and are generally planar in shape. In one implementation, the electrodes and metadielectric material layer 23 are in the form of long strips of material that are sandwiched together and wound into a coil along with an insulating material, e.g., a plastic film such as polypropylene or polyester to prevent electrical shorting between electrodes 21 and 22.

[0072] In order that the invention may be more readily understood, reference is made to the following examples, which are intended to be illustrative of the invention, but are not intended to limit the scope.

EXAMPLE 1

[0073] ##STR00032##

[0074] 2-decyl-1-tetradecanol (1 equiv.), PPh.sub.3 (2 equiv.), and DIAD (2.3 equiv.) were dissolved in THF and stirred in an ice bath. Then, 2-amino-5-nitrophenol was added and the reaction was allowed to warm to ambient temperature and stirred for 24 h. The reaction mixture was diluted with hexanes and filtered through diatomaceous earth. The filtrate was concentrated and purified on silica gel to give 1.

##STR00033##

[0075] 2-(N-ethylanilino)ethanol (1 equiv.), NaH (2 equiv.), and tosyl chloride (1.2 equiv.) were dissolved in DMF and stirred at room temperature for 18 h. The solution was processed through an aqueous workup. The organics were dried over MgSO.sub.4 and the solvents were removed en vacuo.

##STR00034##

[0076] 2-decyl-1-tetradecanol (1 equiv.), NaH (2 equiv.), and tosylated 2-(N-ethylanilino)ethanol (1 equiv.) were dissolved in THF and stirred at room temperature for 18 h. The solution was processed through an aqueous workup. The organics were dried over MgSO.sub.4 and the solvents were removed en vacuo to give 2.

##STR00035##

[0077] Compound 1 (20 mmol) was dissolved in a solution of 35% hydrochloric acid and the mixture was stirred in an ice bath. Subsequently, a water solution of sodium nitrite (20 mmol) was added slowly and the resulting solution was stirred in the ice bath for 30 min, a solution of 2 (24 mmol) in distilled ethanol was added dropwise and stirred for 1 h. After pH of the resulting solution was adjusted to 7.0 with potassium carbonate, the reaction was stirred for another 30 min. The red solution was diluted with CH.sub.2Cl.sub.2 and washed with brine and deionized water. The crude product was purified by recrystallization.

[0078] While the above is a complete description of the preferred embodiment of the present invention, it is possible to use various alternatives, modifications and equivalents. Therefore, the scope of the present invention should be determined not with reference to the above description but should, instead, be determined with reference to the appended claims, along with their full scope of equivalents. Any feature described herein, whether preferred or not, may be combined with any other feature described herein, whether preferred or not. In the claims that follow, the indefinite article “A”, or “An” refers to a quantity of one or more of the item following the article, except where expressly stated otherwise. As used herein, in a listing of elements in the alternative, the word “or” is used in the logical inclusive sense, e.g., “X or Y” covers X alone, Y alone, or both X and Y together, except where expressly stated otherwise. Two or more elements listed as alternatives may be combined together. The appended claims are not to be interpreted as including means-plus-function limitations, unless such a limitation is explicitly recited in a given claim using the phrase “means for.”