Synthesis of Poly(arylene vinylene)s Containing Carbazole, Triphenylamine, and Phenothiazine Rings in the Backbone by Cascade Suzuki-Heck Reactions

Abstract Three new conjugated poly(arylene vinylene) structures containing triphenylamine, carbazole, or phenothiazine as aromatic units in the main chain and connected by vinyl segments have been synthesized by a cascade Suzuki-Heck reactions. The best reaction yields were obtained by coupling of the dibromoarylamines with vinyl segments via Suzuki-Heck reaction cascade using Pd(OAc)2 as catalyst and triethylamine as solvent. The polymers were obtained as fully or partially soluble materials in chlorinated or aprotic polar solvents. They were characterized by 1H-NMR, FT-IR, UV-Vis, and photoluminescence spectroscopy. Cyclic voltammetry characteristics were studied in solution and as solid thin films deposited on the electrode surface. Keywords: Arylaminescarbazoleoptoelectronic propertiesphenothiazinepoly(arylenevinylene)sSuzuki-Heck reactiontriphenylamine Acknowledgements The authors wish to express their gratitude to the Romanian National Authority for Scientific Research (UEFISCSU) for financial support (Grant PN II-IDEI-993, Contract 649/2009). Notes A) Using Pd(PPh3)4/ K2CO3/dioxane system. B) Using Pd(AcO)2, P(o-Tol)3/Et3 N/dioxane system. a) Number-average molecular weights. PDI = Mw/Mn. a Determined in diluted CHCl3 solution;. b Eg = 1240/ λ onset obtained from UV-Vis spectra. Eg = EHOMO - ELUMO.