Photoisomerization of fluorinated 1,3-dimethyl-5-propenyl uracils as a cycle of sequential reactions: Electrocyclization in its use in light-fueled nanomotors

作者: Tomasz Siodla , Marcin Hoffmann , Piotr Karwatka , Henryk Koroniak

DOI: 10.1016/J.MOLSTRUC.2010.10.029

关键词: PhotochemistryPericyclic reactionPhotoisomerizationChemistryCyclobuteneTorquoselectivityIsomerizationPropenylDieneConrotatory and disrotatory

摘要: Abstract Research in the last ten years has demonstrated that light energy can be used to power artificial nanomotors by exploiting photochemical processes appropriately designed systems. The properties of fluorinated derivatives 1,3-dimethyl-5-propenyl uracils were studied assuming electrocyclization diene would a dominant reaction. primarily formed intermediate, cyclobutene derivative was expected undergo further electrocyclic conrotatory ring-opening leading corresponding E or Z isomer. Keeping mind Woodward–Hoffmann and torquoselectivity rules, this photoisomerization is stereospecific reaction, where isomerization each isomers through different trans–cis cyclobutene-intermediates. This cycle sequent reactions capable provide selective 360° clockwork rotation, which as model design light-fueled nanomotor.

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