Journal article
Syntheses and spectral properties of functionalized, water-soluble BODIPY derivatives
Department of Chemistry, Texas A & M University, Box 30012, College Station, Texas 77841, USA.1
The objective of this work was to form water-soluble 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives. Sulfonation conditions were developed for several BODIPY dyes to give the monosulfonated products 1a-3a and the disulfonated products 1b-3b. Compounds 1 are functionalized with an aryl iodide for organometallic couplings.
Similarly, 2 has an aromatic bromide but also two chlorine atoms that could be replaced via SNAr reactions. The amine 3 is amenable to couple to biomolecules via acylation reactions. A diazotization/azide reaction sequence was used to convert the amines 3 into azides 4; the latter may be functionalized via click reactions as illustrated by conversion of 4b into 5.
Compound 5 was designed to have an acid-functional group to facilitate activation and coupling to amines. Spectral data for these materials indicate they are highly fluorescent probes in aqueous environments.
Language: | English |
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Year: | 2008 |
Pages: | 1963-1970 |
ISSN: | 15206904 and 00223263 |
Types: | Journal article |
DOI: | 10.1021/jo702463f |