Gas phase formation of phenalene via 10π-aromatic, resonantly stabilized free radical intermediates. Issue 27 (29th June 2020)

• Record Type: Journal Article
• Authors: Zhao, Long; Kaiser, Ralf I.; Lu, Wenchao; Ahmed, Musahid; Oleinikov, Artem D.; Azyazov, Valeriy N.; Mebel, Alexander M.; Howlader, A. Hasan; Wnuk, Stanislaw F.
• Is Part Of: Physical chemistry chemical physics. Volume 22:Issue 27(2020)
• Page Start: 15381
• Page End: 15388
• Publication Date: 2020-06-29
• Subjects: Chemistry, Physical and theoretical -- Periodicals; 541.3
• DOI: 10.1039/d0cp02216k
• Languages: English
• ISSNs: 1463-9076

Abstract

Abstract : 1 H -Phenalene can be synthesized via the reaction of the 1-naphthyl radical with methylacetylene and allene under high temperature conditions prevalent in carbon-rich circumstellar environments and combustion systems. Abstract : For the last few decades, the Hydrogen-Abstraction/aCetylene-Addition (HACA) mechanism has been fundamental in aiding our understanding of the source of polycyclic aromatic hydrocarbons (PAHs) in combustion processes and in circumstellar envelopes of carbon rich stars. However, the reaction mechanisms driving high temperature molecular mass growth beyond triphenylene (C18 H12 ) along with the link between PAHs and graphene-type nanostructures as identified in carbonaceous meteorites such as in Murchison and Allende has remained elusive. By exploring the reaction of the 1-naphthyl radical (C10 H7 ˙) with methylacetylene (CH3 CCH) and allene (H2 CCCH2 ) under conditions prevalent in carbon-rich circumstellar environments and combustion systems, we provide compelling evidence on a facile formation of 1 H -phenalene (C13 H10 ) – the central molecular building block of graphene-type nanostructures. Beyond PAHs, molecular mass growth processes from 1 H -phenalene via ring-annulation through C3 molecular building blocks may ultimately lead to two-dimensional structures such as graphene nano flakes and after condensation of multiple layers to graphitized carbon. These fundamental reaction mechanisms are of crucial significance to facilitate an understanding of the origin and chemical evolution of carbon in our Galaxy.