Synthesis and electrochromic properties of conducting copolymers of dioxocino- and dithiocino-quinoxalines with bithiophene

Abstract

Two new monomers, 2-benzyl-5,12-dihydro-2H-pyrrolo[3 0 ,4 0 :2,3][1,4]dioxocino [6,7-b]quinoxaline (DPOQ) and 5,12-dihydrothieno[3 0 ,4 0 :2,3][1,4]dithiocino[6,7-b]quinoxaline (DTTQ), were synthesized. The chemical structures of the monomers were characterized by nuclear magnetic resonance ( 1 H NMR), Fourier transform infrared (FTIR) and mass spectra. Copolymer of DPOQ with bithiophene (BT) was synthesized via potentiostatic electrochemical polymerization in acetonitrile-tetrabutylammonium tetrafluoroborate solventelectrolyte couple. For DTTQ, copolymerization with bithiophene was achieved via potentiodynamic method in dichloromethane-tetrabutylammonium hexafluorophosphate solvent-electrolyte couple. Characterizations of the resulting copolymers were performed by cyclic voltammetry (CV), FTIR, scanning electron microscopy (SEM) and UV-Vis spectroscopy. Four-probe technique was used to measure the conductivities of the samples. Moreover, the spectroelectrochemical and electrochromic properties of the copolymer films were investigated. In addition, dual type polymer electrochromic devices based on P(DPOQ-co-BT) and P(DTTQ-co-BT) with poly(3,4-ethylenedioxythiophene) were constructed. Spectroelectrochemistry, electrochromic switching and open circuit stability of the devices were studied. They were found to have good switching times, reasonable contrasts and optical memories.

Low-potential electrosynthesis of a novel nitrogen analog of PEDOT in an ionic liquid and its optoelectronic properties

“…The vibration modes from the C-S bond in the thiophene ring could be seen at 670 cm-1, while the strong absorption band at 838 cm-1 was attributed to the dopant anion PF6-during doping process, which was corresponding to the reported literatures [41,42]. In Table 1 The low-energy peak had an absorption maximum at 603 nm for PMDTO, which was assumed as a result of the π-π* absorption, implying the existence of conjugated segments in the polymer.…”

A Low Band Gap Benzimidazole Derivative and Its Copolymer with 3,4-Ethylenedioxythiophene for Electrochemical Studies

“…In literature, this strategy was applied for different CPs to improve the mentioned properties. [3][4][5][6][7][8] Due to outstanding electrochemical properties such as; low oxidation potential, good stability and low bandgap, EDOT is one of the excellent candidates for electrochemical copolymerization. 23 As a result, in this study copolymerization technique was applied to improve the electrochemical properties of this novel monomer (BIMN) by insertion of EDOT unit.…”

“…[3][4][5] Over the last two decades conducting polymers (CPs) have received considerable attention due to their electrochemical and optical properties, [6][7][8] low cost, tunable band gaps [3][4][5] and fast switching times. 9 Modification of bandgap of conducting polymer is a crucial strategy to achieve desirable electrochromic properties.…”

Measurement and correlation of the solubility of 2,3,4,5-tetrabromothiophene in different solvents

“…As reported in the literature [6,7], tetrabromothiophene is obtained by the reaction of thiophene with bromine in trichloromethane. Crude tetrabromothiophene is yielded after adjusting PH and filtrating and pure tetrabromothiophene can be gained by re-crystallization in trichloromethane solution.…”