Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril.

ABSTRACT: We introduce herein boron-dipyrromethene (BODIPY) dyes as a new class of fluorophores for the design of reporter dyes for supramolecular host-guest complex formation with cucurbit[7]uril (CB7). The BODIPYs contain a protonatable aniline nitrogen in the meso-position of the BODIPY chromophore, which was functionalized with known binding motifs for CB7. The unprotonated dyes show low fluorescence due to photoinduced electron transfer (PET), whereas the protonated dyes are highly fluorescent. Encapsulation of the binding motif inside CB7 positions the aniline nitrogen at the carbonyl rim of CB7, which affects the pK_a value, and leads to a host-induced protonation and thus to a fluorescence increase. The possibility to tune binding affinities and pK_a

SUBMITTER: Alnajjar MA 

PROVIDER: S-EPMC6122296 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature