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Rational Topological Design for Fluorescence Enhancement upon Aggregation of Distyrylfuran Derivatives
Author(s) -
Mallet Charlotte,
Moussallem Chady,
Faurie Alexandre,
Allain Magali,
Gohier Frédéric,
Skene William G.,
Frère Pierre
Publication year - 2015
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.201500023
Subject(s) - fluorescence , rational design , topology (electrical circuits) , biological system , chemistry , photochemistry , computer science , nanotechnology , materials science , mathematics , physics , biology , optics , combinatorics
A series of 2,5‐distyrylfuran derivatives bearing pentafluorophenyl‐ and cyanovinyl units have been synthesized for aggregation‐induced emission (AIE). The effect of the type and extent of the supramolecular connections on the AIE of the furan derivatives were examined and correlated with their X‐ray crystal structures. It was found that the simultaneous presence of cyano and perfluorophenyl units strongly enhances the fluorescence upon aggregation. Single‐crystal X‐ray diffraction analysis confirmed that CH⋅⋅⋅F, F⋅⋅⋅F, CH⋅⋅⋅nitrile, Ar⋅⋅⋅Ar F (Ar=aryl, Ar F =fluoroaryl), and nitrile⋅⋅⋅Ar F intra‐ and intermolecular interactions drive the topology of the molecule and that solid‐state supramolecular contacts favor AIE of the furan derivatives.