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

Bioorg Med Chem Lett. 2015 Dec 15;25(24):5716-9. doi: 10.1016/j.bmcl.2015.10.091. Epub 2015 Oct 30.

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.

Keywords: BODIPY; Bathochromism; Cell imaging; Crystal structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Boron Compounds / pharmacology
  • Butadienes / chemistry*
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology
  • HeLa Cells
  • Humans
  • Light
  • Magnetic Resonance Spectroscopy
  • Microscopy, Fluorescence
  • Molecular Conformation

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Butadienes
  • Fluorescent Dyes
  • 1,3-butadiene