New non-traditional organogelator of β-diketone-boron difluoride complexes with terminal tetraphenylethene: Self-assembling and fluorescent sensory properties towards amines

New beta-diketone-boron difluoride complexes functionalized with tetraphenylethene (TPEB, DTPEB and TTPEB) which exhibit AIE (aggregation-induced emission) properties have been synthesized. It was found that only boomerang-shaped DTPEB without any traditional gelation groups could form organogel in specific organic solvents. It gave strong orange red fluorescence in organogel as well as in xerogel-based film although it was non-emissive in solution. It is interesting that the emission of DTPEB in xerogel-based film could be quenched significantly upon exposure to triethylamine (TEA) vapour, and the detection limit was as low as ca. 0.1 ppb. This work provides a strategy for the synthesis of a new rigid non-traditional pi-gelator via the construction of a boomerang-shaped pi-conjugated skeleton. In addition, the gelation of the pi-gelators with AIE ability is a facile method for the fabrication of luminescent organic nanomaterials. (C) 2017 Elsevier Ltd. All rights reserved.