Single Benzene Green Fluorophore: Solid‐State Emissive,Water‐Soluble,and Solvent‐ and pH‐Independent Fluorescence with Large Stokes Shifts |
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| Authors: | Teruo Beppu Kosuke Tomiguchi Prof. Dr. Akito Masuhara Prof. Dr. Yong‐Jin Pu Prof. Dr. Hiroshi Katagiri |
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| Affiliation: | Graduate School of Science and Engineering, Yamagata University, 4‐3‐16 Jonan, Yonezawa, Yamagata 992‐8510 (Japan) |
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| Abstract: | Benzene is the simplest aromatic hydrocarbon with a six‐membered ring. It is one of the most basic structural units for the construction of π conjugated systems, which are widely used as fluorescent dyes and other luminescent materials for imaging applications and displays because of their enhanced spectroscopic signal. Presented herein is 2,5‐bis(methylsulfonyl)‐1,4‐diaminobenzene as a novel architecture for green fluorophores, established based on an effective push–pull system supported by intramolecular hydrogen bonding. This compound demonstrates high fluorescence emission and photostability and is solid‐state emissive, water‐soluble, and solvent‐ and pH‐independent with quantum yields of Φ=0.67 and Stokes shift of 140 nm (in water). This architecture is a significant departure from conventional extended π‐conjugated systems based on a flat and rigid molecular design and provides a minimum requirement for green fluorophores comprising a single benzene ring. |
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| Keywords: | fluorescence hydrogen bonds solid‐state emission stokes shifts water solubility |
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