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 monosulfonatedproducts
1a-
3a and the disulfonated products
1b-
3b. Compounds
1 are functionalized with an aryliodide for organometallic couplings. Similarly,
2 has an aromatic bromide but also two chlorine atomsthat could be replaced via S
NAr reactions. The amine
3 is amenable to couple to biomolecules via acylationreactions. A diazotization/azide reaction sequence was used to convert the amines
3 into azides
4; thelatter may be functionalized via click reactions as illustrated by conversion of
4b into
5. Compound
5was designed to have an acid-functional group to facilitate activation and coupling to amines. Spectraldata for these materials indicate they are highly fluorescent probes in aqueous environments.
