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

Cassandra Fleming (Institutionen för kemi och kemiteknik, Fysikalisk kemi) ; Patricia Remón (Institutionen för kemi och kemiteknik, Fysikalisk kemi) ; Shiming Li (Institutionen för kemi och kemiteknik, Fysikalisk kemi) ; N. A. Simeth ; B. Konig ; M. Grotli ; Joakim Andréasson (Institutionen för kemi och kemiteknik, Fysikalisk kemi)
Dyes and pigments (0143-7208). Vol. 137 (2017), p. 410-420.
[Artikel, refereegranskad vetenskaplig]

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).

Nyckelord: Photochromism, Photoswitches, Diarylmaleimides, Photoisomerization



Denna post skapades 2017-01-16. Senast ändrad 2017-09-14.
CPL Pubid: 247082

 

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Institutioner (Chalmers)

Institutionen för kemi och kemiteknik, Fysikalisk kemi

Ämnesområden

Kemi

Chalmers infrastruktur