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A visible-light-dri...
A visible-light-driven molecular motor based on barbituric acid
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- Kuntze, Kim (author)
- Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands.;Tampere Univ, Fac Engn & Nat Sci, FI-33101 Tampere, Finland.
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- Pooler, Daisy R. S. (author)
- Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands.
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- Di Donato, Mariangela (author)
- European Lab Non Linear Spect LENS, via N Carrara 1, I-50019 Sesto Fiorentino, Italy.;ICCOM CNR, via Madonna Piano 10, I-50019 Sesto Fiorentino, FI, Italy.
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- Hilbers, Michiel F. (author)
- Univ Amsterdam, Vant Hoff Inst Mol Sci, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands.
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- van der Meulen, Pieter (author)
- Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands.
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- Buma, Wybren Jan (author)
- Univ Amsterdam, Vant Hoff Inst Mol Sci, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands.;Radboud Univ Nijmegen, Inst Mol & Mat, FELIX Lab, Toernooiveld 7c, NL-6525 ED Nijmegen, Netherlands.
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- Priimagi, Arri (author)
- Tampere Univ, Fac Engn & Nat Sci, FI-33101 Tampere, Finland.
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- Feringa, Ben L. (author)
- Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands.
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- Crespi, Stefano (author)
- Uppsala universitet,Syntetisk molekylär kemi,Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands.
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Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands;Tampere Univ, Fac Engn & Nat Sci, FI-33101 Tampere, Finland. Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9746 Groningen, Netherlands. (creator_code:org_t)
- Royal Society of Chemistry, 2023
- 2023
- English.
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In: Chemical Science. - : Royal Society of Chemistry. - 2041-6520 .- 2041-6539. ; 14:32, s. 8458-8465
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https://doi.org/10.1...
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https://uu.diva-port... (primary) (Raw object)
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
- NATURVETENSKAP -- Fysik -- Atom- och molekylfysik och optik (hsv//swe)
- NATURAL SCIENCES -- Physical Sciences -- Atom and Molecular Physics and Optics (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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