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Exceedingly Large Stokes Shift Induced by Low‐Barrier H‐Bond‐Assisted Internal Charge Transfer
Author(s) -
Wang Qin,
Xu Longfei,
Niu Yahui,
Yuan MaoSen,
Zhang Yanrong
Publication year - 2017
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.201700179
Subject(s) - chemistry , stokes shift , benzothiazole , intramolecular force , photochemistry , excited state , fluorescence , aqueous solution , conjugated system , derivative (finance) , internal conversion , stereochemistry , spectral line , organic chemistry , atomic physics , physics , quantum mechanics , astronomy , financial economics , economics , polymer
Abstract By only replacing phenyl group with N ‐methylpyridinium in a 2‐(2‐hydroxyphenyl)benzothiazole (HBT) derivative HBT‐s‐Ph, which is an excited state intramolecular proton transfer (ESIPT)‐active dye, the conjugated HBT– N ‐methylpyridinium hybrid HBT‐Py , emits high‐efficiency fluorescence ( Φ f : 29 %) with an exceedingly large Stokes shift (213 nm) even in aqueous solution. Emission spectroscopy and computational calculations indicate that this typical photophysical property owes to low‐barrier H‐bond (LBHB)‐assisted internal charge transfer (ICT), not ESIPT.