Gas phase synthesis of [4]-helicene

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

doi:10.1038/s41467-019-09224-8

Title: Gas phase synthesis of [4]-helicene

Journal Article · Wed Apr 03 00:00:00 EDT 2019 · Nature Communications

DOI:https://doi.org/10.1038/s41467-019-09224-8· OSTI ID:1546667

Zhao, Long ^[1];

^[1]; Xu, Bo ^[2]; Ablikim, Utuq ^[2]; Lu, Wenchao ^[2];

^[2]; Evseev, Mikhail M. ^[3]; Bashkirov, Eugene K. ^[3]; Azyazov, Valeriy N. ^[3]; Zagidullin, Marsel V. ^[3]; Morozov, Alexander N. ^[4]; Howlader, A. Hasan ^[4];

^[4]; Mebel, Alexander M. ^[5]; Joshi, Dharati ^[6]; Veber, Gregory ^[6]; Fischer, Felix R. ^[7]

Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Samara National Research Univ. (Russia)
Florida Intl Univ., Miami, FL (United States)
Samara National Research Univ. (Russia); Florida Intl Univ., Miami, FL (United States)
Univ. of California, Berkeley, CA (United States)
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Florida International Univ. (FIU), Miami, FL (United States); Univ. of Hawaii, Honolulu, HI (United States); Univ. of Hawaii at Manoa, Honolulu, HI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; Ministry of Education and Science of the Russian Federation

Grant/Contract Number:: AC02-05CH11231; FG02-03ER15411; FG02-04ER15570; SC0010409; DEFG02- 03ER15411; 14.Y26.31.0020

OSTI ID:: 1546667

Alternate ID(s):: OSTI ID: 1594767; OSTI ID: 1603093

Journal Information:: Nature Communications, Vol. 10, Issue 1; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 23 works

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