Synthesis, spectral properties and photostability of novel boron-dipyrromethene dyes

Aijun Cui, Xiaojun Peng, Jiangli Fan, Xiuying Chen, Yunkou Wu, Binchen Guo

Research output: Contribution to journalArticle

Abstract

Two series of novel boron-dipyrromethene (BODIPY) dyes containing 8-phenyl groups have been synthesized and their spectral properties have been studied. Series 2 with four methyl groups at 1,3,5,7-positions show much higher fluorescence quantum yields and extinction coefficients than series 1 (without methyl groups). The "push-pull" electronic effect caused by the methyl groups at 3 and 5 positions is a significant positive factor to the high quantum yields of 2. The X-ray structure analysis of 1c and 2c reveals that steric expulsion exists between the phenyl and adjacent two methyl groups. Moreover, the steric expulsion might block the intramolecular vibronic relaxation and internal conversion of the excited 2, which also contributes to their high fluorescence quantum yields. The substituent effects on photostability and redox potentials of these dyes have been discussed.

Original languageEnglish (US)
Pages (from-to)85-92
Number of pages8
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume186
Issue number1
DOIs
StatePublished - Feb 5 2007
Externally publishedYes

Keywords

  • Boron-dipyrromethene dye
  • Crystal structure
  • Cyclovoltammetry
  • Fluorescence quantum yield
  • Internal conversion
  • Intramolecular vibronic relaxation
  • Photostability

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

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