A visible-light-driven molecular motor based on barbituric acid
| العنوان: | A visible-light-driven molecular motor based on barbituric acid |
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| المؤلفون: | Kuntze, Kim, Pooler, Daisy R. S., Di Donato, Mariangela, Hilbers, Michiel F., van der Meulen, Pieter, Buma, Wybren Jan, Priimagi, Arri, Feringa, Ben L., Crespi, Stefano |
| المصدر: | Chemical Science. 14(32):8458-8465 |
| الوصف: | We present a class of visible-light-driven molecular motors based on barbituric acid. Due to a serendipitous reactivity we observed during their synthesis, these motors possess a tertiary stereogenic centre on the upper half, characterised by a hydroxy group. Using a combination of femto- and nanosecond transient absorption spectroscopy, molecular dynamics simulations and low-temperature H-1 NMR experiments we found that these motors operate similarly to push-pull second-generation overcrowded alkene-based molecular motors. Interestingly, the hydroxy group at the stereocentre enables a hydrogen bond with the carbonyl groups of the barbituric acid lower half, which drives a sub-picosecond excited-state isomerisation, as observed spectroscopically. Computational simulations predict an excited state "lasso" mechanism where the intramolecular hydrogen bond pulls the molecule towards the formation of the metastable state, with a high predicted quantum yield of isomerisation (68%) in gas phase. |
| وصف الملف: | electronic |
| URL الوصول: | https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-511720 https://doi.org/10.1039/d3sc03090c https://uu.diva-portal.org/smash/get/diva2:1800565/FULLTEXT01.pdf |
| قاعدة البيانات: | SwePub |
| DOI: | 10.1039/d3sc03090c |
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