The present invention relates to an electrode layer comprising a porous film made of oxide semiconductor fine particles sensitized with a quinolinium dye having a fluorinated counteranion. Moreover the present invention relates to a photoelectric conversion device comprising said electrode layer, a dye sensitized solar cell comprising said photoelectric conversion device and to novel quinolinium dyes having a fluorinated counteranion.

Photochromic tetrahydroindolizines (THIs) bearing dihydroisoquinoline derivatives as heterocyclic bases and central fluorene groups have been synthesized via different chemical and photochemical pathways. Three alternative pathways for the synthesis of the target photochromic THI-based pyridazinopyrrolo[1,2-b]isoquinolines via in situ trapping with hydrazine hydrate are also provided. High product yields are obtained using different Sonogashira-mediated coupling reactions provided herein. Low temperature multichannel UV-vis and flash photolysis techniques were used to detect the photochromic and kinetic properties of the synthesized system.

The present disclosure concerns the design, formulations, preparations and optical properties of compounds of Formulas (I) and (VI):
(charged dye.sup.m+).sub.x.Math.(counterion.sup.n).sub.y.Math.(counterion receptor).sub.z(I) and
(charged dye.sup.m).sub.x.Math.(counterion.sup.n+).sub.y.Math.(counterion receptor).sub.z(VI). The charged dye.sup.m+ is a cationic dye, counterion.sup.n is an anion, and counterion receptor is a binding ligand for the counterion.sup.n, wherein m, n, x and y are integers greater than or equal to 1, and products of x.Math.n and m.Math.y are identical for formula (I). The charged dye.sup.m is a anionic dye, counterion.sup.n+ is a cation, and counterion receptor is a binding ligand for the counterion.sup.n+, wherein m, n, x and y are integers greater than or equal to 1, and products of x.Math.n and m.Math.y are identical for formula (VI).

The present disclosure is directed, in general, to (1) nonlinear optical (NLO) chromophores, including (2) compositions/materials/resistive layers comprising NLO chromophores, and the methods of making the compositions/materials/resistive layers comprising NLO chromophores (e.g., methods of poling and/or drying, and the like), (3) uses of NLO chromophores in electro-optic devices (e.g., electro-optic modulators (EOMs)). NLO chromophores disclosed herein not only have large EO effect, but also have fast modulation speed. In addition, NLO chromophores disclosed herein have superior refractive index, photostability and thermal stability compared to other EO Materials. As a consequence, NLO chromophores herein are particularly suited for use as EO materials in connection with low power and small footprint devices, including devices used in data acquisition systems, analog I/O modules, field transmitters, lab and field instrumentation, servo drive control modules, direct current (DC) power supply, alternating current (AC), and/or electronic load.

The present disclosure is directed, in general, to nonlinear optical (NLO) chromophores comprising donating groups of the following general structure (D.sup.1):

##STR00001##

where R.sub.1 can be a substituted or unsubstituted aryl or a substituted or unsubstituted alkyl. R.sub.2 can be a substituted or unsubstituted aryl, a substituted or unsubstituted alkyl or a ring-locked structure. In some embodiments, R.sub.1 and R.sub.2 can together form a ring structure. In some embodiments, R.sub.2 can be a ring-locked structure forming a ring with the phenyl group of the formula (D.sup.1). In certain embodiments, n is 1 or 2.