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Organometallic synthesis of n‐type π‐conjugated polymers with dopant cation trapping sites and stability of n‐doping state against air
Author(s) -
Yamaguchi Isao,
Uehara Ryohei
Publication year - 2013
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.4361
Subject(s) - conjugated system , polymer , acetonitrile , dopant , ring (chemistry) , pyridine , polymer chemistry , doping , materials science , electrochemistry , thiophene , photochemistry , chemistry , organic chemistry , optoelectronics , electrode
n‐Type π‐conjugated polymers comprising a 1,2,4‐triazole ring substituted by a benzo‐15‐crown 5‐ether (benzo15C5) subunit at the 4‐position of the 1,2,4‐triazole ring and n‐type aromatic rings such as pyridine‐2,5‐diyl and 2,1,3‐benzothiadiazole‐4,7‐diyl rings were synthesized by organometallic polycondensation. The UV‐visible spectra of the polymers exhibited absorption maxima (λ max values) at a longer wavelength than that exhibited by 3,5‐bis(2‐bromopyridyl)‐4‐benzo15C5‐1,2,4‐triazole, revealing that their π‐conjugation system was expanded along the polymer chain. The polymers with the benzo15C5 subunit underwent an electrochemical reduction (n‐doping), and the corresponding oxidation (n‐dedoping) occurred at an unusually high potential in an acetonitrile solution of NaClO 4 ; the factor responsible for the unusually high oxidation potential was the stabilized n‐doping state that was attributed to the inclusion of Na + in the 15C5 ring. The polymers with the benzo15C5 subunit exhibited a considerably higher stability of the n‐doping state in air than did those without this subunit. Copyright © 2012 Society of Chemical Industry