Single‐Benzene‐Based Solvatochromic Chromophores: Color‐Tunable and Bright Fluorescence in the Solid and Solution States. Issue 72 (6th December 2019)

• Record Type: Journal Article
• Authors: Liu, Huijing; Yan, Sisi; Huang, Rongrong; Gao, Zhipeng; Wang, Gang; Ding, Liping; Fang, Yu
• Is Part Of: Chemistry. Volume 25:Issue 72(2019)
• Page Start: 16732
• Page End: 16739
• Publication Date: 2019-12-06
• Subjects: chromophores -- fluorescence -- mechanochromic luminescence -- solvatochromic behavior -- solvent effects; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904478
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Polar opposites : A single‐benzene‐based solvatochromic chromophore with a wide range of solvent compatibility exhibits bright fluorescence in both solid and solution states and possesses reversible mechanochromic luminescence (see figure).