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.


Fused structures in the polymer backbone to investigate the photovoltaic and electrochromic properties of donoracceptor-type conjugated polymers
CEVHER, ŞEVKİ CAN; UNLU, Naime Akbasoglu; OZELCAGLAYAN, Ali Can; APAYDIN, Dogukan Hazar; Udum, Yasemin Arslan; Toppare, Levent Kamil; Çırpan, Ali (Wiley, 2013-05-01)
In this study, two new benzotriazole (BTz) and dithienothiophene (DTT) containing conjugated polymers were synthesized. After successful characterizations of the monomers by proton-nuclear magnetic resonance (1H NMR) and carbon-NMR (13C NMR) techniques, poly(4-(dithieno[3, 2-b:2,3-d]thiophen-2-yl)-2-(2-octyldodecyl)-2H-benzo[d][1,2,3] triazole) P1 and poly(4-(5-(dithieno[3,2-b:2,3-d]thiophen-2-yl)thiophen-2-yl)-2-(2-octyldodecyl)-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole) P2 were synthesized via a typica...
Synthesis and optical properties of light-emitting π-conjugated polymers containing biphenyl and dithienosilole
LIAO, Liang; Çırpan, Ali; CHU, Qinghui; KARASZ, Frank E.; PANG, YI (Wiley, 2007-05-15)
Copolymers containing oligo(phenylene vinylene) (2.5), fluorene, and 4,4-dihexyldithienosilole (DTS) units were synthesized and characterized. The pi-conjugated monomers were joined with the palladium(0)-catalyzed Suzuki-Miyaura coupling reaction, thus forming either biphenyl- or phenyl-thiophene linkages. These polymers were photoluminescent, with the fluorescent quantum efficiency between 54 and 63% and with),lambda(max) for fluorescence at similar to 448 nm in tetrahydrofuran. The presence of 5% DTS in t...
Synthesis and characterization of thiophen-3-yl acetic acid 4-pyrrol-1-yl phenyl ester and its conducting polymers
BINGÖL, Bahar; GÜNER, Yusuf; Çırpan, Ali; Toppare, Levent Kamil (Informa UK Limited, 2005-08-01)
Thiophen-3-yl acetic acid 4-pyrrol-1-yl phenyl ester (TAPE) monomer was synthesized via reaction of thiophen-3-yl acetyl chloride with 4-pyrrol-1-yl phenol. Homopolymers were achieved by using electrochemical and chemical polymerization techniques. Copolymers of TAPE with bithiophene or pyrrole were synthesized by potentiostatic electrochemical polymerization in acetonitrile-tetrabutylammonium tetrafluoroborate (TBAFB) solvent-electrolyte couple. The chemical structures were confirmed by both Nuclear Magnet...
Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization
Yilmaz, F; Cianga, L; Guner, Y; Topppare, L; Yagci, Y (Elsevier BV, 2004-08-05)
A novel N-(4-(3-thienyl methylene)-oxycarbonylphenyl) maleimide (MBThi) monomer was synthesized by the esterification reaction of maleimidobenzoic acid (MBA) with 3-thiophene methanol. Photoinduced radical polymerization was employed to prepare the alternating copolymers of MBThi with styrene (St) at room temperature using omega,omega-dimethoxy-omega-phenylacetophenone (DMPA) as photoinitiator. Different copolymerization conditions were examined to estimate the influence of the used solvents and comonomers'...
Synthesis of conducting polysiloxane-polypyrrole graft copolymers
Gunaydin, O; Toppare, Levent Kamil; Yagci, Y; Harabagiu, V; Pintela, M; Simionescu, BC (Springer Science and Business Media LLC, 2002-02-01)
Polysiloxane-polypyrrole graft copolymers have been synthesized by a series of chemical reactions and subsequent electropolymerization. First, the hydrosilation of 4-vinyl aniline by dimethyl-methylhydrosiloxane copolymer gave the corresponding aminophenyl functional polydimethylsiloxane (PDMS-NH2). The side chain pyrrole functionalized. polysiloxanes were then prepared by the reaction of PDMS-NH2 with glycidylpyrrole. Finally, the synthesis of graft copolymers of polysiloxane and pyrrole has been achieved ...
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.