Compressing a Non-Planar Aromatic Heterocyclic [7]Helicene to a Planar Hetero[8]Circulene
Publikation: Bidrag til tidsskrift › Letter › Forskning › fagfællebedømt
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Compressing a Non-Planar Aromatic Heterocyclic [7]Helicene to a Planar Hetero[8]Circulene. / Lousen, Bodil; Pedersen, Stephan K.; Bols, Pernille; Hansen, Kasper H.; Pedersen, Michelle R.; Hammerich, Ole; Bondarchuk, Sergey; Minaev, Boris; Baryshnikov, Glib V.; Ågren, Hans; Pittelkow, Michael.
I: Chemistry - A European Journal, Bind 26, Nr. 22, 2020, s. 4935-4940.Publikation: Bidrag til tidsskrift › Letter › Forskning › fagfællebedømt
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TY - JOUR
T1 - Compressing a Non-Planar Aromatic Heterocyclic [7]Helicene to a Planar Hetero[8]Circulene
AU - Lousen, Bodil
AU - Pedersen, Stephan K.
AU - Bols, Pernille
AU - Hansen, Kasper H.
AU - Pedersen, Michelle R.
AU - Hammerich, Ole
AU - Bondarchuk, Sergey
AU - Minaev, Boris
AU - Baryshnikov, Glib V.
AU - Ågren, Hans
AU - Pittelkow, Michael
PY - 2020
Y1 - 2020
N2 - 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).
AB - 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).
KW - chirality
KW - helicenes
KW - non-planar aromatics
KW - structure/property relations
KW - synthetic methodology
U2 - 10.1002/chem.201905339
DO - 10.1002/chem.201905339
M3 - Letter
C2 - 32052498
AN - SCOPUS:85082079748
VL - 26
SP - 4935
EP - 4940
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 22
ER -
ID: 238954231