Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 28, Pages 5460-5468Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100736
Keywords
BODIPY; Fluorescence; Dyes; pigments; Synthetic methods
Categories
Funding
- National Nature Science Foundation of China [20802002, 20902004, 20972001, 21072005]
- Anhui Province [090416221, KJ2009A130]
- Scientific Research Foundation for Returned Overseas Chinese Scholars, the State Education Ministry
- Ministry of Education of China [20093424120001]
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Formylation has been performed on pyrrole-unsubstituted dipyrromethanes 1 and boron-dipyrrin (BODIPY) dyes 4 based on a Vilsmeier-Haack reaction. It is highly regioselective and complementary and occurs exclusively at the alpha- and beta-position, respectively, for pyrrole-unsubstituted dipyrromethanes 1 and BODIPY dyes 4. This regioselective formylation enables the syntheses of a variety of alpha- and beta-substituted BODIPY dyes. The installation of formyl groups affects the electronic properties of the BODIPY chromophore, resulting in red-and blueshifts of the absorption and emission maxima, respectively, for the alpha- and beta-formylated BODIPYs 3 and 5.
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