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Single‐Benzene‐Based Solvatochromic Chromophores: Color‐Tunable and Bright Fluorescence in the Solid and Solution States
Author(s) -
Liu Huijing,
Yan Sisi,
Huang Rongrong,
Gao Zhipeng,
Wang Gang,
Ding Liping,
Fang Yu
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904478
Subject(s) - chromophore , solvatochromism , fluorescence , benzene , photochemistry , materials science , chemistry , optics , physics , organic chemistry
The search for structurally simple chromophores with superior fluorescence brightness and a wide range of solvent compatibility is highly desirable. Herein, a new type of single‐benzene‐based solvatochromic chromophore with a symmetric bifunctional structure, in which azetidine and ethoxycarbonyl moieties serve as the electron‐donating and ‐withdrawing groups, respectively, is reported. This chromophore exhibits an extraordinary wide range of solvent compatibility and preserves excellent fluorescence quantum yields from nonpolar n ‐hexane to polar methanol and even in water. Unusually, the symmetric structure of the chromophore shows a distinct color change from bright green to red with increasing solvent polarity and possesses large Stokes shifts ( λ =132–207 nm) in the tested solvents. Moreover, this single‐benzene‐based chromophore displays good photochemical stability in both solution and solid states, and even exhibits reversible mechanochromic luminescence.