On the use of diarylmaleimide derivatives in biological contexts: An investigation of the photochromic properties in aqueous solution
Journal article, 2017

A series of photochromic diarylmaleimide derivatives has been synthesized and studied with respect to the photochromic properties in aqueous solution. The main rationale is to investigate if these compounds could be used as photoswitchable units in biological contexts, motivated by the fact that the diarylmaleimide structural motif is identified in many pharmacophores. Thus, photoswitchable variants of this class of compounds could be very useful in the quest for photoactivatable drugs. The photoinduced cyclization reaction (colorization) is suppressed in solvents of high polarity, whereas the ring-opening reaction (decolorization) still occurs with high efficiency. The photochromically active anti-parallel conformer of the open form is more abundant in the asymmetrically substituted derivatives, which in turn favors the formation of the closed isomeric form. The rates of the thermal isomerization reactions have also been assessed, together with the resistance toward thermal degradation. Here it was observed that the maleimide derived compounds were not susceptible to the thermally driven reactions (hydrolysis and isomerization).

Photochromism

Photoisomerization

Photoswitches

Diarylmaleimides

Author

Cassandra Fleming

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Patricia Remón Ruiz

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Shiming Li

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

N. A. Simeth

University of Regensburg

B. Konig

University of Regensburg

Morten Grötli

University of Gothenburg

Joakim Andreasson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Dyes and Pigments

0143-7208 (ISSN)

Vol. 137 410-420

Subject Categories

Chemical Sciences

DOI

10.1016/j.dyepig.2016.10.023

More information

Latest update

4/18/2018