Gas-Phase Synthesis of Triphenylene (C18H12)

Zhao, Long; Xu, Bo; Ablikim, Utuq; Lu, Wenchao; Ahmed, Musahid; Evseev, Mikhail M.; Bashkirov, Eugene K.; Azyazov, Valeriy N.; Howlader, A. Hasan; Wnuk, Stanislaw F.; Mebel, Alexander M.; Kaiser, Ralf I.

doi:10.1002/cphc.201801154

Gas-Phase Synthesis of Triphenylene (C₁₈H₁₂)

Journal Article · Thu Jan 31 23:00:00 EST 2019 · ChemPhysChem

DOI:https://doi.org/10.1002/cphc.201801154· OSTI ID:1603092

Zhao, Long ^[1]; Xu, Bo ^[2]; Ablikim, Utuq ^[2]; Lu, Wenchao ^[2]; Ahmed, Musahid ^[2]; Evseev, Mikhail M. ^[3]; Bashkirov, Eugene K. ^[3]; Azyazov, Valeriy N. ^[4]; Howlader, A. Hasan ^[5]; Wnuk, Stanislaw F. ^[5]; Mebel, Alexander M. ^[6]; ^[7]

Univ. of Hawaii at Manoa, Honolulu, HI (United States). Dept. of Chemistry; University of Hawaii at Manoa
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
Samara National Research Univ. (Russia)
Samara National Research Univ. (Russia); Lebedev Physical Inst. of RAS, Samara (Russia). Dept. of Chemical and Electric Discharge Lasers
Florida International Univ., Miami, FL (United States). Dept. of Chemistry and Biochemistry
Samara National Research Univ. (Russia); Florida International Univ., Miami, FL (United States). Dept. of Chemistry and Biochemistry
Univ. of Hawaii at Manoa, Honolulu, HI (United States). Dept. of Chemistry

For the last decades, the hydrogen-abstraction-acetylene-addition (HACA) mechanism has been widely invoked to rationalize the high-temperature synthesis of PAHs as detected in carbonaceous meteorites (CM) and proposed to exist in the interstellar medium (ISM). By unravelling the chemistry of the 9-phenanthrenyl radical ([C₁₄H₉]$$^\bullet$$) with vinylacetylene (C₄H₄) during our work, we present the first compelling evidence of a barrier-less pathway leading to a prototype tetracyclic PAH – triphenylene (C₁₈H₁₂) – via an unconventional hydrogen abstraction–vinylacetylene addition (HAVA) mechanism operational at temperatures as low as 10 K. The barrier-less, exoergic nature of the reaction reveals HAVA as a versatile reaction mechanism that may drive molecular mass growth processes to PAHs and even two-dimensional, graphene-type nanostructures in cold environments in deep space thus leading to a better understanding of the carbon chemistry in our universe through the untangling of elementary reactions on the most fundamental level.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Hawaii, Honolulu, HI (United States); Florida International Univ., Miami, FL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division; Ministry of Education and Science of the Russian Federation

Grant/Contract Number:: FG02-03ER15411; FG02-04ER15570; AC02-05CH11231

OSTI ID:: 1603092

Alternate ID(s):: OSTI ID: 1608266
OSTI ID: 1494647

Journal Information:: ChemPhysChem, Journal Name: ChemPhysChem Journal Issue: 6 Vol. 20; ISSN 1439-4235

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C 10 H 7 ) to benzindenes (C 13 H 10 ) as a case study Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I. Physical Chemistry Chemical Physics, Vol. 21, Issue 30 https://doi.org/10.1039/c9cp02930c	journal	January 2019
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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
gas-phase chemistry
hydrogen abstraction−vinylacetylene addition (HAVA)
interstellar medium
mass spectrometry
polycyclic aromatic hydrocarbons