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Synthesis of a Multifunctional Quinoxaline and Benzodithiophene Bearing Polymer and Its Electrochromic Device Applications
Author(s) -
Yasa Mustafa,
Surmeli Seher,
Depci Tolga,
Toppare Levent,
Hacioglu Serife Ozdemir
Publication year - 2020
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201900470
Subject(s) - electrochromism , polymer chemistry , stille reaction , quinoxaline , merocyanine , fourier transform infrared spectroscopy , copolymer , pedot:pss , materials science , thiophene , chemistry , polymer , photochemistry , organic chemistry , photochromism , chemical engineering , electrode , engineering
Abstract A quinoxaline (Qx) and benzodithiophene (BDT) comprising of random copolymers, namely poly(5‐(6‐(5‐(4,8‐bis((2‐ethylhexyl)oxy)benzo[1,2‐b:4,5‐b′]dithiophen‐2‐yl)‐4‐(2‐ethylhexyl)thiophen‐2‐yl)‐4,8‐bis ((2‐ethylhexyl)oxy)benzo[1,2‐b:4,5‐b′]dithiophen‐2‐yl)‐2,3‐bis(3,4‐bis(octyloxy)phenyl)quinoxaline) (PQBT), is synthesized via Stille polycondensation reaction. To investigate the effect of the π‐bridge on the electrochromic properties, 3‐(2‐ethylhexyl) thiophene is incorporated the between Qx and BDT moiety. The resulting random copolymer is characterized by NMR spectroscopy, gel permeation chromatography (GPC), attenuated total reflectance−Fourier‐transform infrared spectroscopy (ATR−FTIR), and scanning electron microscopy (SEM). PQBT exhibits ambipolar and multichromic characteristics and is highly soluble in common solvents. Optoelectronic studies reveal two well‐separated absorption bands having maxima at 500 and 532 nm with 1.83 eV optical band gap ( E g op ). PQBT exhibits orange color in the neutral state with brown, green, and blue colors in the intermediate, oxidized, and reduced states, respectively. Subsequently, a PQBT and poly‐3,4‐ethylenedioxythiophene (PEDOT)‐bearing prototype bilayer electrochromic device working between orange and blue colors is constructed and characterized.