MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

Jun Cheng Er, Mui Kee Tang, Chee Geng Chia, Huimin Liew, Marc Vendrell, Young-Tae Chang

Research output: Contribution to journalArticlepeer-review

Abstract

A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.

Original languageEnglish
Pages (from-to)2168-2176
Number of pages9
JournalChemical Science
Volume4
Issue number5
DOIs
Publication statusPublished - 2013

Keywords

  • HUMAN-SERUM-ALBUMIN
  • CRYSTALLOGRAPHIC ANALYSIS REVEALS
  • QUANTUM-CHEMICAL CALCULATIONS
  • SPECIES-DEPENDENT BINDING
  • DRUG-BINDING
  • CRYSTAL-STRUCTURE
  • STRUCTURAL BASIS
  • ENERGY-TRANSFER
  • FATTY-ACIDS
  • SPECTRAL PROPERTIES

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