New fluorescent imidazo[1,2-a]pyridine-BODIPY chromophores: Experimental and theoretical approaches, and cell imaging exploration

• Published in: Dyes and pigments 2017-07, Vol.142, p.330-339
• Main Authors: Wu, Yuxiao, Yuan, Wei, Ji, Heyi, Qin, Yaru, Zhang, Jin, Li, Hongkun, Li, Yahong, Wang, Yong, Sun, Yufang, Liu, Wei
• Format: Article
• Language: English
• Subjects: BODIPY; Crystal structure; Emission; Imidazo[1,2-a]pyridine; Quantum yield; TDDFT calculations
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2017.03.052

Based on imidazo[1,2-a]pyridine derivatives, a series of mononuclear and binuclear fluorine-boron complexes 1a,b, 4a,b, and 5a,b have been designed and synthesized. X-ray crystal structures for single boron-core complexes 1b, 4a, 4b, and dual boron-core imidazo[1,2-a]pyridine-BODIPY dyad 5b were obtained, and intermolecular CH⋯F interactions were observed in their solid state. High absorption coefficients, strong emissions, and high photostabilities have been demonstrated for these boron complexes. DFT and TD-DFT studies reveal efficient electronic interactions between the imidazo[1,2-a]pyridine moiety and BODIPY plane for dyads 4a,b, and 5a,b. Cell imaging of 4a was tested to show good cellular uptake ability. [Display omitted] •We synthesize two novel boron complexes based on imidazo[1,2-a]pyridine and four imidazo[1,2-a]pyridine-BODIPY dyads.•DFT and TDDFT calculations have provided insight into interpreting the electronic properties.•Luminescent emissions were investigated, and one imidazo[1,2-a]pyridine-BODIPY dyad 4a can be used as effective cell imaging regent.