A new organic far-red mechanofluorochromic compound derived from cyano-substituted diarylethene

A new cyano-substituted diarylethene derivative (R-NH2) with reversible far-red mechanofluorochromic property was synthesized and confirmed by standard spectroscopic methods. To the best of our knowledge, the 684 nm red-shifted wavelength of the ground R-NH2 is the longest wavelength that has appeared in the literature. The mechanofluorochromic mechanism was investigated by small and wide-angle X-ray scattering and was ascribed to the destruction of crystalline structure. More in-depth study by infrared spectra and time-resolved emission-decay behaviors showed that the changes of C H out-of-plane bending vibrations in aryl group of the compound and the obvious increase of fluorescence lifetime might be the fundamental reasons. The synthetic strategy reported here can be extended to prepare more and more long-wavelength emission mechanofluorochromic materials, which can broaden the scope of application of such materials and for thoroughly understanding the mechanofluorochromic mechanism. (C) 2013 Elsevier Ltd. All rights reserved.