Improving the Fatigue Resistance of Diarylethene Switches

被引：316

作者：

Herder, Martin ^{[1
]}

Schmidt, Bernd M. ^{[1
]}

Grubert, Lutz ^{[1
]}

Paetzel, Michael ^{[1
]}

Schwarz, Jutta ^{[1
]}

Hecht, Stefan ^{[1
]}

机构：

[1] Humboldt Univ, Dept Chem, D-12489 Berlin, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 07期

基金：

欧洲研究理事会;

关键词：

IRREVERSIBLE PHOTOCHROMIC SYSTEMS; REVERSIBLE PHOTOCYCLIZATION; LIGHT; DITHIENYLETHENES; MECHANISM; DITHIENYLCYCLOPENTENES; PHOTOSWITCHES; AROMATICITY; MOLECULES; MEMORIES;

D O I：

10.1021/ja513027s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

When applying photochromic switches as functional units in light-responsive materials or devices, an often disregarded yet crucial property is their resistance to fatigue during photoisomerization. In the large family of diarylethene photoswitches, formation of an annulated isomer as a byproduct of the photochromic reaction turns out to prevent the desired high reversibility for many different derivatives. To overcome this general problem, we have synthesized and thoroughly investigated the fatigue behavior of a series of diarylethenes, varying the nature of the hetaryl moieties, the bridging units, and the substituents. By analysis of photokinetic data, a quantification of the tendency for byproduct formation in terms of quantum yields could be achieved, and a strong dependency on the electronic properties of the substituents was observed. In particular, substitution with 3,5-bis(trifluoromethyl)phenyl or 3,5-bis(pentafluorosulfanyl)phenyl groups strongly suppresses the byproduct formation and opens up a general strategy to construct highly fatigue-resistant diarylethene photochromic systems with a large structural flexibility.

引用

页码：2738 / 2747

页数：10

共 76 条

[11] Single-molecule fluorescence photoswitching: Design and synthesis of photoswitchable fluorescent molecules [J].