Syntheses of new monomeric and polymeric units and electrochemical behaviors for the use in electrochromic applications

Zaifoğlu, Nazlı Buket
4'-(Tert-butyl)-4,7-di(thiophen-2-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane], 4,7-di([2,2'-bithiophen]-5-yl)-4'-(tert-butyl)spiro[benzo[d]imidazole-2,1'-cyclohexane], 4'-(tert-butyl)-4,7-bis(thieno[3,2-b]thiophen-2-yl)spiro[benzo[d]imidazole-2,1'- cyclohexane] were synthesized, electrochemically polymerized and electrochromic properties of resultant polymers were investigated. The monomers were characterized by nuclear magnetic resonance spectroscopy (1H-NMR, 13C-NMR). Cyclic voltammetry (CV) and ultraviolet–visible spectroscopy techniques were used to investigate electrochemical behavior of the monomers and redox behaviors of the conducting polymers. After electrochemical polymerization, the electrochromic properties of the conducting polymers were investigated via spectroelectrochemical, and kinetic studies. Poly-(2-(4-(hexadecyloxy)phenyl)-5-methyl-10-(5-methylthiophen-2-yl)-1- phenyl-1H-phenanthro[9,10-d]imidazole), poly-(2-(4-(hexadecyloxy)phenyl)-5-methyl- 10-(5'-methyl-[2,2'-bithiophen]-5-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole) were synthesized and their electrochromic properties were investigated. For the characterization of the polymers gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) were used. Cyclic voltammetry (CV) and ultraviolet–visible spectroscopy were used to investigate electrochemical behavior and redox reactions of conducting polymers.


Syntheses and Electrochemical Characterization of Low Oxidation Potential Nitrogen Analogs of Pedot as Electrochromic Materials
Hacioglu, Serife O.; Yigit, Deniz; Ermis, Emel; Soylemez, Saniye; GÜLLÜ, Mustafa; Toppare, Levent Kamil (The Electrochemical Society, 2016-01-01)
In this study, the electropolymerization of ethyl andmethyl substituted asymmetrical nitrogen analogs of 3,4-ethylenedioxythiophene (OEt and OMe) were synthesized, characterized and their electrochemical properties were investigated. Both polymers (POEt and POMe) were synthesized electrochemically and characterized using spectroelectrochemical technique to determine optical changes of the resulting polymer films. Electrochemical studies demonstrated that these polymers exhibited a significantly low oxidatio...
Electrochromic properties and electrochromic device application of copolymer of N-(4-(3-thienyl methylene)-oxycarbonylphenyl)maleimide with thiophene
Ak, Metin; Camurlu, Pinar; Yilmaz, Faruk; Cianga, Luminita; Yagci, Yusuf; Toppare, Levent Kamil (2006-12-05)
A new copolymer of N-(4-(3-thienyl methylene)-oxycarbonylphenyl)maleimide (MBThi) with thiophene [P(MBThi-co-Th)] was synthesized electrochemically in the presence of tetrabutylammonium tetrafluoroborate as the supporting electrolyte, in acetonitrile/borontrifluoride ethylether solvent mixture (80 : 20, v/v). Spectroelectrochemical analysis of the resulting copolymer reflected electronic transitions at 440, 730, and similar to 1000 nm, revealing pi-pi* transition, polaron, and bipolaron band formation, resp...
Synthesis and characterization of a bifunctional amido-thiophene monomer and its copolymer with thiophene and electrochemical properties
AK, M; Çırpan, Ali; Yılmaz, Fatih; YAGCI, Y; Toppare, Levent Kamil (2005-05-01)
A bifunctional amido-thiophene namely hexamethylene (bis-3-thiophene acetamide) (HMTA) was synthesized by the reaction of 3-thiophene acetic acid with hexamethylene diamine. Copolymerization in the presence of thiophene was achieved electrochemically in tetrabutylammonium tetrafluoroborate/acetonitrile (TBAFB/AN). Spectroelectro-chemical analysis of the resulting copolymer [P(HMTA-co-Th)] reflected electronic transitions at 505 nm, 740 nm and similar to 1000 nm, revealing pi to pi* transition, polaron and b...
Syntheses of conducting polymers of 3-ester substituted thiophenes and characterization of their electrochromic properties
Çamurlu, Pınar; Toppare, Levent Kamil; Department of Chemistry (2006)
In this study three different 3-ester substituted thiophene monomers were synthesized via esterification reaction of 3-thiophene ethanol with adipoyl chloride or sebacoyl chloride or octanoyl chloride in the presence of triethylamine at 00C. Characterizations of the monomers were performed by 1H-NMR, 13C-NMR, FTIR, DSC, TGA techniques. Electrochemical behavior of the monomers both in presence or absence of BFEE were studied by cyclic voltammetry. Results showed the astonishing effect of BFEE on the polymeri...
Chemoenzymatic synthesis of chiral hydroxymethyl cycloalkenols
Şenocak, Deniz; Demir, Ayhan Sıtkı; Department of Chemistry (2004)
Chiral cyclic alkenols with hydroxymethyl functionality are important structural units in many biologically active natural compouds such as prostaglandins, sesquiterpene antiviral agents, pentenomycins, xanthocidin, sarkomycin, etc. 1,3-cycloalkanediones are converted into bicyclic polyoxo derivatives with formaldehyde and trioxane in the presence of Lewis acid. Selective oxidation of the bicyclic compounds by using manganese(III)acetate followed by enzyme-catalyzed kinetic resolution afforded chiral bicycl...
Citation Formats
N. B. Zaifoğlu, “Syntheses of new monomeric and polymeric units and electrochemical behaviors for the use in electrochromic applications,” M.S. - Master of Science, Middle East Technical University, 2013.