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A Near‐Infrared Emissive π‐Conjugated Polymer Consisting of an Excited‐State Intramolecular Proton Transfer Unit
Author(s) -
Suzuki Naoya,
Wakioka Masayuki,
Ozawa Fumiyuki,
Yamaguchi Shigehiro
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000234
Subject(s) - chemistry , intramolecular force , conjugated system , photochemistry , polymer , excited state , thiazole , luminescence , proton , optoelectronics , organic chemistry , materials science , physics , quantum mechanics , nuclear physics
Near infrared (NIR)‐emissive polymers are attractive luminescent materials due to their utilities in biological, optoelectronic, and telecommunication applications. Herein we report the use of a dialkylamine‐strapped dithienylpyrrole (DTP) as an excited‐state intramolecular proton transfer (ESIPT) building block for producing NIR‐emissive π‐conjugated polymers. The study of a series of model compounds showed that the extension of π‐conjugation with a moderately electron‐accepting comonomer unit, dithientyl‐substituted thiazolo[5,4‐d]thiazole (TzTz), effectively stabilizes the zwitterionic ESIPT state while increasing the oscillator strength for the electronic transition from the ESIPT state. Consequently, a polymer consisted of DTP and TzTz units exhibited a significantly red‐shifted emission, exceeding 750 nm, from the ESIPT state in polar solvents.