Synthesis, Crystal Structure and Photophysical Properties of Bromothiophene-Functionalized BF 2 -Curcuminoid as a Versatile Building Block.

A novel bromothiophene-functionalized BF 2 -curcuminoid (BTC-BF 2 ) was synthesized by Knoevenagel condensation reaction. The structure of BTC-BF 2 was determined by 1 H NMR, 13 C NMR and HRMS. Moreover, a nearly coplanar single crystal structure was successfully obtained and form a mesh structure through intermolecular multiple C-H···F hydrogen bond interactions. As expected, as-prepared BTC-BF 2 exhibited solvent-dependent photophysical properties in solvents with different polarity and an intense red solid-state fluorescence. DFT calculations further verified the relationships between its intrinsic electronic features and the photophysical properties. For its potential application aspect, BTC-BF 2 showed a certain ability to generate singlet oxygen under irradiation with 530 nm green light. Moreover, BTC-BF 2 can be utilized as versatile building block to construct novel far-red or NIR BF 2 -curcuminoid complexes for widely biological applications. This article is protected by copyright. All rights reserved.