Syntheses and spectral properties of functionalized, water-soluble BODIPY derivatives. Academic Article uri icon


  • 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.

published proceedings

  • J Org Chem

altmetric score

  • 15

author list (cited authors)

  • Li, L., Han, J., Nguyen, B., & Burgess, K.

citation count

  • 197

complete list of authors

  • Li, Lingling||Han, Junyan||Nguyen, Binh||Burgess, Kevin

publication date

  • March 2008