Divinyl BODIPY derivative: Synthesis, photophysical properties, crystal structure, photostability and bioimaging

• Published in: Bioorganic & medicinal chemistry letters 2015-12, Vol.25 (24), p.5716-5719
• Main Authors: Yang, Liutao, Liu, Ying, Liu, Wei, Ma, Chunping, Zhang, Chun, Li, Yang
• Format: Article
• Language: English
• Subjects: Bathochromism; BODIPY; Boron Compounds - chemical synthesis; Boron Compounds - chemistry; Boron Compounds - pharmacology; Butadienes - chemistry; Cell imaging; Cell Survival - drug effects; Crystal structure; Crystallography, X-Ray; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent Dyes - pharmacology; HeLa Cells; Humans; Light; Magnetic Resonance Spectroscopy; Microscopy, Fluorescence; Molecular Conformation
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2015.10.091

[Display omitted] 4,4-Difluoro-3,5-bis(3,3-dimethyl-1-butenyl)-8-anthryl-4-bora-3a,4a-diaza-s-indacene (1), a symmetric fluorescent difluoroboron dipyrromethene dye, was produced in Knoevenagel reaction involving 4,4-difluoro-3,5-bis(methyl)-8-anthryl-4-bora-3a,4a-diaza-s-indacene (2) and pivaldehyde. Its crystal structure was determined by single crystal X-ray diffraction analysis, and the photophysical properties were investigated. The BODIPY 1 exhibits significant bathochromic shifts in both absorption and fluorescence spectrum compared with the BODIPY 2. In addition, the BODIPY 1 exhibited small energy gaps (2.11eV). The extensive π conjugation is responsible for their red-shifted emission. Cell imaging experiments demonstrated its potential application as a biological fluorescent probe due to its excellent imaging contrast.