Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
6492573 | Journal of Photochemistry and Photobiology A: Chemistry | 2018 | 33 Pages |
Abstract
A novel red fluorescent probe based on boron dipyrromethene (BODIPY) was successfully designed and synthesized, consisting of electron acceptor 1,3,5,7-tetramethyl-8-phenyl-BODIPY (BDP) and electron donor triphenylamine (TPA) units using Suzuki cross-coupling methods TPA-BDP exploits the advantages of both aggregation-induced emission (AIE) and twisted intramolecular charge transfer (TICT). An X-ray crystal structure of TPA-BDP reveals a network of CHâ¯F intermolecular interactions which can contribute to rigidifying the molecular conformation. Thereby, aggregation restricts the intramolecular rotation associated with the donor moiety, inducing a great enhancement in the emission efficiency. This new dye features high sensitivity and excellent selectivity to fluoride ions with a detection limit of 0.73â¯Î¼M in aqueous medium. The sensing mechanism was systematically investigated by 1H NMR, 19F NMR, 11B NMR and mass spectrometry. It is proposed that fluoride reacts in a nucleophilic displacement reaction at the BDP core which disrupts the structure of TPA-BDP, thereby causing the red fluorescence of TPA-BDP quenched. It is noteworthy that TPA-BDP has been utilized for the fluorescence imaging and fluoride ions detection in living cells with very low cytotoxicity.
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Authors
Weilong Che, Guangfu Li, Jianxu Zhang, Yun Geng, Zhigang Xie, Dongxia Zhu, Zhongmin Su,