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Compressing a Non-P...
Compressing a Non-Planar Aromatic Heterocyclic [7]Helicene to a Planar Hetero[8]Circulene
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Lousen, B. (author)
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Pedersen, S. K. (author)
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Bols, P. (author)
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Hansen, K. H. (author)
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Pedersen, M. R. (author)
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Hammerich, O. (author)
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Bondarchuk, S. (author)
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Minaev, B. (author)
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- Baryshnikov, Gleb V. (author)
- KTH,Teoretisk kemi och biologi
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- Ågren, Hans (author)
- KTH,Teoretisk kemi och biologi,College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan, 475004 P. R. China
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Pittelkow, M. (author)
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(creator_code:org_t)
- 2020-03-20
- 2020
- English.
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In: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 26:22, s. 4935-4940
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- This work describes a synthetic approach where a non-planar aromatic heterocyclic [7]helicene is compressed to yield a hetero[8]circulene containing an inner antiaromatic cyclooctatetraene (COT) core. This [8]circulene consists of four benzene rings and four heterocyclic rings, and it is the first heterocyclic [8]circulene containing three different heteroatoms. The synthetic pathway proceeds via a the flattened dehydro-hetero[7]helicene, which is partially a helicene and partially a circulene: it is non-planar and helically chiral as helicenes, and contains a COT motif like [8]circulenes. The antiaromaticity of the COT core is confirmed by nucleus independent chemical shift (NICS) calculations. The planarization from a helically π-conjugated [7]helicene to a fully planar heterocyclic [8]circulene significantly alters the spectroscopic properties of the molecules. Post-functionalization of the [7]helicenes and the [8]circulenes by oxygenation of the thiophene rings to the corresponding thiophene-sulfones allows an almost complete fluorescence emission coverage of the visible region of the optical spectrum (400–700 nm).
Subject headings
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
Keyword
- chirality
- helicenes
- non-planar aromatics
- structure/property relations
- synthetic methodology
- Aromatization
- Chemical shift
- Stereochemistry
- Thiophene
- Fluorescence emission
- Nucleus independent chemical shifts
- Post-functionalization
- Spectroscopic property
- Organic polymers
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Lousen, B.
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Pedersen, S. K.
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Bols, P.
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Hansen, K. H.
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Pedersen, M. R.
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Hammerich, O.
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show more...
-
Bondarchuk, S.
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Minaev, B.
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Baryshnikov, Gle ...
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Ågren, Hans
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Pittelkow, M.
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show less...
- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Theoretical Chem ...
- Articles in the publication
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Chemistry - A Eu ...
- By the university
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Royal Institute of Technology