A visible-light-driven molecular motor based on barbituric acid

Kim Kuntze, Daisy R.S. Pooler, Mariangela Di Donato, Michiel F. Hilbers, Pieter van der Meulen, Wybren Jan Buma, Arri Priimagi, Ben L. Feringa*, Stefano Crespi*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

4 Citaten (Scopus)
9 Downloads (Pure)

Samenvatting

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 1H 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.

Originele taal-2English
Pagina's (van-tot)8458-8465
Aantal pagina's8
TijdschriftChemical Science
Volume14
Nummer van het tijdschrift32
Vroegere onlinedatum20-jul.-2023
DOI's
StatusPublished - 28-aug.-2023

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