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Issue 23, 2015
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Functionalization of photochromic dithienylmaleimides

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Photochromic dithienylmaleimides are well known molecular switches, but for applications the suitable functionalization of the photochromic scaffold is required. We report here synthetic routes to dithienylmaleimides, which are functionalized at three different positions: at each of the thiophene moieties and the maleimide nitrogen. A Perkin-type condensation of two thiophene precursors is used as the key step to assemble the maleimide core, which allows the synthesis of non-symmetrically substituted dithienylmaleimides, such as photochromic amino acids. A different approach to the maleimide core is provided by the reaction of a dithienylmaleic anhydride with amines or hydrazides leading to maleimide protected dithienylmaleimides and photochromic labeled natural amino acids. The photochromic properties of the new photoswitches were investigated showing reversible photochromism in polar organic solvents.

Graphical abstract: Functionalization of photochromic dithienylmaleimides

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Article information

01 Jan 2015
04 Feb 2015
First published
04 Feb 2015

This article is Open Access

RSC Adv., 2015,5, 18075-18086
Article type
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Functionalization of photochromic dithienylmaleimides

D. Wutz, C. Falenczyk, N. Kuzmanovic and B. König, RSC Adv., 2015, 5, 18075
DOI: 10.1039/C5RA00015G

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