Journal
TETRAHEDRON
Volume 67, Issue 17, Pages 3105-3110Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.02.073
Keywords
BODIPY dye; Fluorescence; Near-infrared; C-H arylation; Charge transfer
Categories
Funding
- Japan Society for the Promotion of Science (JSPS) [22350087, B-09]
- Grants-in-Aid for Scientific Research [22350087] Funding Source: KAKEN
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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. (C) 2011 Elsevier Ltd. All rights reserved.
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