Synthesis And Property Study Of New D-A Model Organic Photoelectricity Materials

D-A(Donor-Acceptor) binary system materials among all organic photovoltaic materials currently reported reveals excellent photoelectric performance and is receiving more and more attentions.D-A(Donor-Acceptor) binary system materials have many advantages to others. They process separation and transfer of holes and electrons at the same time and are freely soluble in the conventional organic solvents.Furthermore, spectrum and energy levels could be adjusted by changing the molecular structure and connection type of donor and acceptor. And photoinduced charge transfer and energy transfer can take place between donor and acceptor.Therefore, they have a very good application prospect. As electron donors,triphenylamine dyes have attracted a wide spread attention because of their high molar absorption coefficient, good electron-donating ability and hole migration performance.In this work, we synthesized a series of stytyl triphenylamine, carbazole and indoline derivatives connecting the triazine and systematically investigated their optical and electrochemical properties. Ullmann reaction was employed to realize the C-N coupling and the synthetic method has been optimized. Vilsmeier reaction has then been conducted to introduce aldehyde groups into the triphenylamine,9-phenylcarbazole and 4-phenylindole cores. The intermediates 3a,3b,3c,3d,3e and 3f of target compounds were eventually acquired by building styryl structures via Wittig reaction. The above reaction conditions was studied and explored. Afterwards, we introduced triazine onto styryl triarylamine and got target compounds 5a,5b,5c,5d,5e and 5f. The structures of the synthesized compounds have been characterized using 1H NMR,13 C NMR and HRMS. The monocrystal structure of the representative compound(E)-4-methyl-N-(4-(4-nitrostyryl)phenyl)-N-(p-tolyl) aniline(3b) has been determined to further confirm the structure of the target molecules.Upon synthesis, the optical and electrochemical properties of these molecules have been measured using UV-Vis absorption, steady fluorescence and cyclic voltammetry. All these results above showed that carbazole with coplanar structure possesses a weaker intramolecular charge transfer(ICT) character for triphenylamine;introducing electron-donating groups to triphenylamine could enhance its ICTcharacter; Additionally, indoline was found to show an even better ICT character than triphenylamine.