Achieving Enhanced Photochromic Properties of Diarylethene through Host-Guest Interaction in Aqueous Solution

Chemistry. 2021 Nov 22;27(65):16153-16160. doi: 10.1002/chem.202102731. Epub 2021 Oct 13.

Abstract

Diarylethene (DTE) has been widely used in fluorescence probes, molecular logic gates, optical data-storage devices owing to the excellent photochromic property, while constructing high-performance photochromic DTE in aqueous media remains a big challenge. Herein we present several host-guest systems formed between cucurbit[n]uril (CB[n], n=7, 8, 10) and two water-soluble DTE derivatives 1 and 2. It was found that host-guest interactions not only affect the photophysical properties of photochromic guests, but also make great differences on the photoreaction process. Different host-guest binding behaviors also lead to different effects on the photochromic properties of guests. In the presence of CB[n], both 1 and 2 showed enhanced emission and higher fluorescence quenching ratio at photostationary state. Besides, CB[10]⋅1 exhibited faster response rate in cyclization reaction and better photofatigue resistance than free 1 in aqueous solution, while the supramolecular assembly of (CB[8])n ⋅(2)n showed slower response rate in both directions of the reversible photoreaction. Besides, the photofatigue resistance of 2 can be greatly improved through binding with CB[7]. Our results suggest that host-guest interactions could be an efficient way to improve photochromic properties of DTE in aqueous solution.

Keywords: cucurbit[n]urils; diarylethenes; host-guest recognition; photochromism; response rates.

MeSH terms

  • Bridged-Ring Compounds*
  • Fluorescence
  • Fluorescent Dyes
  • Imidazoles*
  • Water

Substances

  • Bridged-Ring Compounds
  • Fluorescent Dyes
  • Imidazoles
  • Water