Synthesis and Spectroscopy of Benzylamine-Substituted BODIPYs for Bioimaging

Consuelo Ripoll, Cheng Cheng, Emilio Garcia-Fernandez, Jin Li, Angel Orte, Hainam Do, Lijuan Jiao, David Robinson, Luis Crovetto, Juan A. González-Vera, Eva M. Talavera, Jose M. Alvarez-Pez, Noël Boens, María Jose Ruedas-Rama

Research output: Journal PublicationArticlepeer-review

10 Citations (Scopus)

Abstract

Three new boron dipyrromethene (BODIPY) dyes substituted with a benzylamino group at the 3-position have been synthesized from halogenated BODIPYs by nucleophilic substitution. The spectroscopic and photophysical properties have been explored in different solvents and have been compared with an analogous 8-benzylaminoBODIPY derivative. The position of the benzylamino group has a significant influence on the spectral band positions, fluorescence quantum yields, and fluorescence lifetimes. The 8-benzylaminoBODIPY emits in the blue range, whereas the 3-substituted shows green fluorescence. Additionally, the extension of the conjugation at the 5-position of 3-benzylaminoBODIPY produces a bathochromic shift of the absorption and emission spectra. The effect of solvents on their spectroscopic features has been investigated using the generalized Catalán solvent scales. Quantum-chemical calculations have been performed to assess the effect of the position of the substitution on the spectroscopic properties. Finally, the BODIPY dyes have been employed as probes in fluorescence lifetime imaging of living cells, demonstrating their high potential for bioimaging.

Original languageEnglish
Pages (from-to)2561-2571
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number20
DOIs
Publication statusPublished - 7 Jun 2018

Keywords

  • Fluorescent probes
  • Imaging agents
  • Solvatochromism

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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