A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Zhao, Long; Kaiser, Ralf I.; Xu, Bo; Ablikim, Utuq; Ahmed, Musahid; Evseev, Mikhail M.; Bashkirov, Eugene K.; Azyazov, Valeriy N.; Mebel, Alexander M.

doi:10.1002/ange.201913037

Title: A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Journal Article · Thu Jan 23 00:00:00 EST 2020 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201913037· OSTI ID:1593502

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Department of Chemistry University of Hawaii at Manoa Honolulu HI 96822 USA
Chemical Sciences Division Lawrence Berkeley National Laboratory Berkeley CA 94720 USA
Samara National Research University Samara 443086 Russia
Samara National Research University Samara 443086 Russia, Department of Chemistry and Biochemistry Florida International University Miami FL 33199 USA

Abstract A unified low‐temperature reaction mechanism on the formation of acenes, phenacenes, and helicenes—polycyclic aromatic hydrocarbons (PAHs) that are distinct via the linear, zigzag, and ortho ‐condensed arrangements of fused benzene rings—is revealed. This mechanism is mediated through a barrierless, vinylacetylene mediated gas‐phase chemistry utilizing tetracene, [4]phenacene, and [4]helicene as benchmarks contesting established ideas that molecular mass growth processes to PAHs transpire at elevated temperatures. This mechanism opens up an isomer‐selective route to aromatic structures involving submerged reaction barriers, resonantly stabilized free‐radical intermediates, and systematic ring annulation potentially yielding molecular wires along with racemic mixtures of helicenes in deep space. Connecting helicene templates to the Origins of Life ultimately changes our hypothesis on interstellar carbon chemistry.

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Sponsoring Organization:: USDOE

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

OSTI ID:: 1593502

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 132 Journal Issue: 10; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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