title: Divinyl BODIPY derivative: Synthesis, photophysical properties, crystal structure, photostability and bioimaging.
abstract: 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.
authors.affiliation: College of Materials and Metallurgical Engineering, Guizhou Institute of Technology, Guiyang, Guizhou 550003, China; The Collaborative Innovation Center of Special Function Materials of Guizhou Province 2011, China. Electronic address: yangliutao2000@126.com.
authors.forename: Liutao
authors.initials: L
authors.lastname: Yang
authors.affiliation: College of Chemical Engineering, Guizhou Institute of Technology, Guiyang, Guizhou 550003, China. Electronic address: liuychemistry@163.com.
authors.forename: Ying
authors.initials: Y
authors.lastname: Liu
authors.affiliation: College of Materials and Metallurgical Engineering, Guizhou Institute of Technology, Guiyang, Guizhou 550003, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Liu
authors.affiliation: College of Materials and Metallurgical Engineering, Guizhou Institute of Technology, Guiyang, Guizhou 550003, China.
authors.forename: Chunping
authors.initials: C
authors.lastname: Ma
authors.affiliation: College of Materials and Metallurgical Engineering, Guizhou Institute of Technology, Guiyang, Guizhou 550003, China.
authors.forename: Chun
authors.initials: C
authors.lastname: Zhang
authors.affiliation: College of Materials and Metallurgical Engineering, Guizhou Institute of Technology, Guiyang, Guizhou 550003, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Li
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002070:Butadienes / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008856:Microscopy, Fluorescence; D008968:Molecular Conformation
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D002070:Butadienes; D005456:Fluorescent Dyes; C031763:1,3-butadiene
keywords: BODIPY; Bathochromism; Cell imaging; Crystal structure