Synthesis of heterocyclic unit substituted carbazole derivatives and their electrochemical polymerization

Oğuztürk, Hatice Esra
The study comprises synthesis of 3,6 and 2,7 substituted carbazole derivatives. Substitution was done by furan groups. The main purpose to conduct this study is to synthesize new low band gap donor-acceptor type monomers and analyze the differences stem from the substitution site difference and alkyl chain effect attached to the nitrogen atom. For this aim, four monomers; 3,6-Di(2-furyl)-9H-carbazole (3,6-F-Cz-F), 3,6-Di(2-furyl)-9-ethyl-carbazole (3,6-F-N-et-F), 2,7-Di(2-furyl)-9-H-carbazole (2,7-F-Cz-F) , 2,7-Di(2-furyl)-9-(tridecan-7-yl)-9H-carbazole (2,7-F-3DCN-F), were synthesized via Stille Cross Coupling reaction between brominated derivatives of carbazole and furan. The synthesized molecules were characterized by spectroscopic methods such as, NMR, UV-vis, and FTIR. The obtained molecules were investigated in terms of electrochemical polymerization conditions. Polymers of these monomers; poly(3,6-Di(2-furyl)-9H-carbazole) (P(3,6-F-Cz-F)), poly(3,6-Di(2-furyl)-9-ethyl-carbazole) (P(3,6-F-N-et-F)), poly(2,7-Di(2-furyl)-9-H-carbazole) (P(2,7-F-Cz-F), poly(2,7-Di(2-furyl)-9-(tridecan-7-yl)-9H-carbazole) (P(2,7-F-3DCN-F)), were synthesized by electrochemical polymerization with optimized conditions. The characterization of corresponding polymers included analytical and electrochemical methods like FTIR, UV-vis, cyclic voltammetry, spectroelectrochemical methods. After characterization of polymers, polymer films were obtained and optical, electrochemical, morphological and thermal properties of the polymers were investigated.


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Citation Formats
H. E. Oğuztürk, “Synthesis of heterocyclic unit substituted carbazole derivatives and their electrochemical polymerization,” M.S. - Master of Science, Middle East Technical University, 2013.