Highly Twisted Isomers of Triphenylacrylonitrile Derivatives with High Emission Efficiency and Mechanochromic Behavior.

Abstract

Two novel triphenylacrylonitrile derivatives (TPAN-C2 and TPAN-C3) with highly twisted conformations have been successfully prepared by Suzuki coupling reaction. Both of them show mechanochromic (MC) fluorescent behaviour and exhibit remarkable fluorescence redshifts from sky-blue to light green upon fully grinding them. Interestingly, the ground powders recover their original states upon heating at 100 °C for 1 min or fuming with solvents vapour. Such intriguing MC properties of TPAN-C2 and TPAN-C3 are attributed to their phase transitions between crystalline and amorphous states, which are confirmed by powder X-ray diffraction (XRD) data. Moreover, the behaviour of both TPAN-C2 and TPAN-C3 indicates that the aggregation-induced emission (AIE) gives rise to rather high fluorescence quantum efficiencies (Φf ) of 0.78 and 0.97, respectively. The influences of stacking mode and molecular conformation on MC properties and the high Φf of TPAN-C2 and TPAN-C3 are discussed.