Supramolecular interactions induced fluorescent organic nanowires with high quantum yield based on 9,10-distyrylanthracene

Abstract

Three DSA (9,10-distyrylanthracene) derivatives, 9,10-bis(3,5-dimethylstyryl)anthracene (TMDSA), 9,10-bis(3,5-bis(trifluoromethyl)styryl)anthracene (TFMDSA) and 9,10-bis(3,5-difluorostyryl)anthracene (TFDSA) were synthesized and characterized. Here we report their crystal structures, structure-property relationships, and nanowire fabrication. The crystal structures indicate that the three compounds with varying substituents exhibit different molecular packing modes. In particular, introducing a F substituent to generate weak intermolecular C–H⋯F interactions benefits the formation of intermolecular π–π stacking in the TFMDSA and TFDSA crystals. Photophysical investigations and crystal structure analysis indicate that inhibition of vibrational relaxation in the aggregate state should be the origin for the high fluorescence and blueshift in crystals of our materials. By controlling the experimental conditions, TFDSA could easily achieve perfect regular 1D nanowires, in which the weak intermolecular C–H⋯F interaction together with effective π–π interaction play a significant role. High quantum efficiency (75% for TFDSA) and regular 1D nanowires suggest that this kind of material may have potential applications in optoelectronic device applications.