Synthesis and electropolymerization of the phthaocyanines with 4-(2,5-di-2-thiophen-2-yl-pyrrol-1-yl) substituents

Yavuz, Arzu
Bezgin, Buket
Aras, Leyla
Önal, Ahmet Muhtar
Novel tetrakis (4-(2,5-di-2-thiophen-2-yl-pyrrol-1-yl)) substituted metal-free (H2Pc-SNS) and zinc phthalocyanine (ZnPc-SNS) complexes were synthesized and characterized by elemental analysis, Fourier Transform Infrared (FTIR) and UV-vis spectroscopies. The solution redox properties of these complexes were also studied by using cyclic voltammetry (CV) and differential pulse voltammetry (DPV) in dichloromethane (DCM) solution containing 0.1 M tetrabutylammonium perchlorate (TBAP) on platinum electrode. Both of the complexes showed two reversible reduction peaks having ligand-based character and one irreversible oxidation peak. Also, the electrochemical polymerization of these newly synthesized complexes were performed in DCM/TBAP solvent/electrolyte couple. Insoluble turquoise green and black films were deposited on the electrode surface both during repetitive cycling and constant potential electrolysis of H2Pc-SNS and ZnPc-SNS, respectively. Resulting polymer films, P(H2Pc-SNS) and P(ZnPc-SNS), were characterized by UV-vis and FTIR spectroscopic techniques and their electrochemical behavior was investigated utilizing CV. In situ spectroelectrochemical investigations revealed that both P(H2Pc-SNS) and P(ZnPc-SNS) films can be reversibly cycled and exhibit electrochromic behavior. Furthermore, the band gap of P(H2Pc-SNS) and P(ZnPc-SNS) were calculated as 2.38 eV and 2.25 eV, respectively from the on set of pi-pi* transition of the conjugated backbone. Moreover, the fluorescence property of the P(ZnPc-SNS) was investigated in dimethyl sulfoxide (DMSO) and toluene.


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Erden, Ayca; Sahin, Elif; Gullu, Mustafa; Toppare, Levent Kamil (Elsevier BV, 2006-08-01)
(3- {[4-(Thien-3-yl-methoxy)phenoxy]methyl} thiophene) (TMPMT) was synthesized via the reaction of 3-bromomethyl-thiophene with hydroquinone and characterized by nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FTIR). Electrochemical copolymerization of TMPMT with thiophene in acetonitrile/boron trifluoride diethyl etherate (AN/BFEE) solvent mixture was achieved using tetrabutylammonium tetrafluoroborate (TBAFB) as the supporting electrolyte. Resulting copolymer was characterize...
Synthesis and characterization of poly(dibromophenylene oxide)s through thermal decomposition of various transition metal complexes in solid state.
Şanlı, Pınar; Kısakürek, Duygu; Aras, Leyla; Department of Chemistry (2002)
In this study, synthesis and characterization of poly(dibromophenylene oxide)s though thermal decomposition of bis(2,4,6-tribromophenolato)di(N- methyl imidazole) Cu(II), bis(2,4,6-tribromophenolato)di(N-methyl illimidazole)Co(II) and bis(2,4,6-tribromophenolato)di(N-methyl imidazole)Ni(II) complexes in solid state was examined. For the characterization of complexes FTIR, DSC, mass spectroscopy, magnetic susceptibility and C, H,N elemental analysis were performed. Syntheses of the polymer were achieved by t...
Synthesis and electropolymerization of a new ion sensitive ethylenedioxy-substituted terthiophene monomer bearing a quinoxaline moiety
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A new terthienyl based fluorescent polymer bearing pendant quinoxaline moieties directly attached to the 3-positions of the central thiophene ring was synthesized by electrochemical polymerization of 4-(2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophen-3-yl)Pyrrolo[1,2-a]quinoxaline (EE-Q). The corresponding polymer, poly(4-(2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiophen-3-yl)pyrrolo[1,2-a]quinoxaline) P(EE-Q), was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The po...
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Homo-polymers and random co-polymers of electroactive and liquid crystalline monomers, namely 3-thienylmethyl methacrylate (MTM) and 6-(4-cyanobiphenyl-4'-oxy)hexyl acrylate (LC6), were prepared by conventional free radical polymerization. Block co-polymers of MTM and LC6 were also synthesized by using the 1,1-diphenylethene (DPE) method. The obtained random and block co-polymers exhibited liquid crystal behavior depending on the content of the LC6 units. It was found that microphase separation of the polym...
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In this study, polystyrene-block-poly(2-vinylpyridine), PS-b-P2VP, polyisoprene-block-poly(2-vinylpyridne), PI-b-P2VP and poly(methyl metacrylate)-block-poly(2-vinylpyridine), PMMA-b-P2VP, coordinated to Cr metal were synthesized and characterized by Fourier transform infrared, transmission electron microscopy and direct pyrolysis mass spectrometry techniques. Both thermal degradation mechanism and thermal stability of P2VP blocks were affected by the coordination of Cr nanoparticles to nitrogen of pyridine...
Citation Formats
A. Yavuz, B. Bezgin, L. Aras, and A. M. Önal, “Synthesis and electropolymerization of the phthaocyanines with 4-(2,5-di-2-thiophen-2-yl-pyrrol-1-yl) substituents,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 116–122, 2010, Accessed: 00, 2020. [Online]. Available: