Near-infrared BODIPY dyes modulated with spirofluorene moieties

Toshiyuki Kowada, Shuhei Yamaguchi, Hiroki Fujinaga, Kouichi Ohe

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1′H-spiro-[fluorene-9,4′-indeno[1,2-b]pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6′-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt.

Original languageEnglish
Pages (from-to)3105-3110
Number of pages6
JournalTetrahedron
Volume67
Issue number17
DOIs
Publication statusPublished - 2011 Apr 29
Externally publishedYes

Keywords

  • BODIPY dye
  • C-H arylation
  • Charge transfer
  • Fluorescence
  • Near-infrared

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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