Syntheses and spectral properties of functionalized, water-soluble BODIPY derivatives.
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.
Li
Lingling
L
Department of Chemistry, Texas A & M University, Box 30012, College Station, Texas 77841, USA.
Han
Junyan
J
Nguyen
Binh
B
Burgess
Kevin
K
D001896:Boron Compounds / Q000737:chemistry*; D012995:Solubility; D013057:Spectrum Analysis / Q000379:methods*; D013450:Sulfones / Q000737:chemistry; D014867:Water / Q000737:chemistry*
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D013450:Sulfones; D014867:Water