Gas phase synthesis of [4]-helicene View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2019-12

AUTHORS

Long Zhao, Ralf I. Kaiser, Bo Xu, Utuq Ablikim, Wenchao Lu, Musahid Ahmed, Mikhail M. Evseev, Eugene K. Bashkirov, Valeriy N. Azyazov, Marsel V. Zagidullin, Alexander N. Morozov, A. Hasan Howlader, Stanislaw F. Wnuk, Alexander M. Mebel, Dharati Joshi, Gregory Veber, Felix R. Fischer

ABSTRACT

A synthetic route to racemic helicenes via a vinylacetylene mediated gas phase chemistry involving elementary reactions with aryl radicals is presented. In contrast to traditional synthetic routes involving solution chemistry and ionic reaction intermediates, the gas phase synthesis involves a targeted ring annulation involving free radical intermediates. Exploiting the simplest helicene as a benchmark, we show that the gas phase reaction of the 4-phenanthrenyl radical ([C14H9]) with vinylacetylene (C4H4) yields [4]-helicene (C18H12) along with atomic hydrogen via a low-barrier mechanism through a resonance-stabilized free radical intermediate (C18H13). This pathway may represent a versatile mechanism to build up even more complex polycyclic aromatic hydrocarbons such as [5]- and [6]-helicene via stepwise ring annulation through bimolecular gas phase reactions in circumstellar envelopes of carbon-rich stars, whereas secondary reactions involving hydrogen atom assisted isomerization of thermodynamically less stable isomers of [4]-helicene might be important in combustion flames as well. More... »

PAGES

1510

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41467-019-09224-8

DOI

http://dx.doi.org/10.1038/s41467-019-09224-8

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1113182114

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30944302


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