On the use of diarylmaleimide derivatives in biological contexts: An investigation of the photochromic properties in aqueous solution. (February 2017)

• Record Type: Journal Article
• Authors: Fleming, Cassandra; Remón, Patricia; Li, Shiming; Simeth, Nadja Anita; König, Burkhard; Grøtli, Morten; Andréasson, Joakim
• Is Part Of: Dyes and pigments. Volume 137(2017)
• Page Start: 410
• Page End: 420
• Publication Date: 2017-02
• Subjects: Photochromism -- Photoswitches -- Diarylmaleimides -- Photoisomerization; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.10.023
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: 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). Highlights: Photoswitchable diarylmaleimide derivatives have been synthesized in high yield. The target compounds represent photoswitchable variants of known bioactives. All compounds display favorable photochromic properties for biological applications.