A Visible-Near-Infrared Light-Responsive Host-Guest Pair with Nanomolar Affinity in Water

Chemistry. 2019 Mar 7;25(14):3477-3482. doi: 10.1002/chem.201806105. Epub 2019 Feb 12.

Abstract

The discovery of stimuli-responsive high affinity host-guest pairs with potential applications under biologically relevant conditions is a challenging goal. This work reports a high-affinity 1:1 complex formed between cucurbit[8]uril and a water-soluble photochromic diarylethene derivative. It was found that, by confining the open isomer within the cavity of the receptor, a redshift in the absorption spectrum and an enhancement of the photocyclization quantum yield from Φ=0.04 to Φ=0.32 were induced. This improvement in the photochemical performance enables quantitative photocyclization with visible light that, together with the near-infrared light-induced ring-opening reaction and the 100-fold selectivity for the closed isomer, confirms this as an outstanding light-responsive affinity pair.

Keywords: affinity pairs; cucurbiturils; diarylethenes; host-guest systems; photoresponsive assemblies.