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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 CH⋅⋅⋅F, F⋅⋅⋅F, CH⋅⋅⋅nitrile, Ar⋅⋅⋅ArF (Ar=aryl, ArF =fluoroaryl), and nitrile⋅⋅⋅ArF intra- and intermolecular interactions drive the topology of the molecule and that solid-state supramolecular contacts favor AIE of the furan derivatives.