Issue 32, 2023

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

Abstract

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.

Graphical abstract: A visible-light-driven molecular motor based on barbituric acid

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Article information

Article type
Edge Article
Submitted
16 iyn 2023
Accepted
20 iyl 2023
First published
20 iyl 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 8458-8465

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

K. Kuntze, D. R. S. Pooler, M. Di Donato, M. F. Hilbers, P. van der Meulen, W. J. Buma, A. Priimagi, B. L. Feringa and S. Crespi, Chem. Sci., 2023, 14, 8458 DOI: 10.1039/D3SC03090C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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