• Home
  • Search Results
  • Turn-on mode fluorescent diarylethenes: effect of electron-donating and electron-withdrawing substituents on photoswitching performance.

Turn-on mode fluorescent diarylethenes: effect of electron-donating and electron-withdrawing substituents on photoswitching performance.

Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology (2020-05-21)
Ryota Iwai, Masakazu Morimoto, Masahiro Irie
ABSTRACT

Diarylethene derivatives having benzothiophene S,S-dioxide groups undergo turn-on mode fluorescence photoswitching. For the practical application to super-resolution fluorescence microscopy, photoswitchable fluorescent molecules are desired to be resistant against photodegradation. Here we synthesized turn-on mode fluorescent diarylethenes having electron-withdrawing (trifluoromethyl or nitro) or electron-donating (methyl, methoxy, or dimethylamino) substituents on phenyl rings at 6- and 6'-positions of the benzothiophene S,S-dioxide groups and examined the effect of the substituents on the photoswitching performance. The derivatives having electron-donating substituents showed significant bathochromic shifts of the absorption and fluorescence spectra. The cycloreversion quantum yield was increased by introducing electron-withdrawing substituents, while it was decreased by the electron-donating ones. Introduction of electron-donating substituents was found to remarkably improve the fatigue resistance of the fluorescent diarylethene under continuous ultraviolet (UV) irradiation. Such highly fatigue-resistant fluorescent diarylethenes are useful for super-resolution fluorescence imaging or single-molecule fluorescence tracking.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Rhodamine 101 inner salt, for fluorescence

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.