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2,6-Bis(arylsulfonyl)anilines as Fluorescent Scaffolds through Intramolecular Hydrogen Bonds: Solid-State
Teruo Beppu1, So Kawata1, Naoya Aizawa1
1Graduate School of Science and Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510 (Japan), Fax: (+81) 238-26-3743.
Abstract:
A series of 2,6-bis[aryl(alkyl)sulfonyl]anilines were synthesized by nucleophilic aromatic substitution of 2,6-dichloronitrobenzene with various aryl or alkyl thiolates (benzyl-, phenyl-, 2-naphthyl-, and 2-aminophenyl thiolate), followed by hydrogenation and subsequent oxidation. All prepared 2,6-bis[aryl-(alkyl)sulfonyl]anilines showed high fluorescence emissions in the solid state; X-ray structures revealed well-defined intramolecular hydrogen bonds, which served to immobilize the rotatable amino group and generate a fluorescence enhancement in addition to improved photostability. Moreover, absorption and fluorescence spectra showed redshifts in the order of benzyl
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