How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10 ) as a case study

Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I.; Xu, Bo; Ablikim, Utuq; Lu, Wenchao; Ahmed, Musahid; Oleinikov, Artem D.; Azyazov, Valeriy N.; Howlader, A. Hasan; Wnuk, Stanislaw F.; Mebel, Alexander M.

doi:10.1039/c9cp02930c

Title: How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C₁₀H₇) to benzindenes (C₁₃H₁₀ ) as a case study

Journal Article · Thu Jul 11 00:00:00 EDT 2019 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/c9cp02930c· OSTI ID:1603183

^[1]; Prendergast, Matthew ^[1];

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

^[2];

^[3];

^[4];

^[5]

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

The three-ring polycyclic aromatic hydrocarbons (PAHs) 3H-benz[e]indene (C₁₃H₁₀) and 1H-benz[f]indene (C₁₃H₁₀) along with their naphthalene-based isomers 2-(prop-2-yn-1-yl)naphthalene (C₁₃H₁₀), 2-(prop-1-yn-1-yl)naphthalene (C₁₃H₁₀), and 2-(propa-1,2-dien-1-yl)naphthalene (C₁₃H₁₀) were formed through a “directed synthesis” via a high temperature chemical micro reactor under combustion-like conditions (1300 ± 35 K) through the reactions of the 2-naphthyl isomer (C₁₀H₇˙) with allene (C₃H₄) and methylacetylene (C₃H₄). The isomer distributions were probed utilizing tunable vacuum ultraviolet radiation from the Advanced Light Source (ALS) by recording the photoionization efficiency curves at mass-to-charge of m/z = 166 (C₁₃H₁₀) and 167 (¹³CC₁₂H₁₀) of the products in a supersonic molecular beam. Complemented by electronic structure calculations, our study reveals critical mass growth processes via annulation of a five-membered ring from the reaction between aryl radicals and distinct C₃H₄ isomers at elevated temperatures as present in combustion processes and in circumstellar envelopes of carbon stars. The underlying reaction mechanisms proceed through the initial addition of the 2-naphthyl radical with its radical center to the π-electron density of the allene and methylacetylene reactants via entrance barriers between 8 and 14 kJ mol^-1, followed by isomerization (hydrogen shifts, ring closure), and termination via atomic hydrogen losses accompanied by aromatization. The reaction mechanisms reflect the formation of indene – the prototype PAH carrying a single five- and a single six-membered ring – synthesized through the reaction of the phenyl radical (C₆H₅˙) with allene and methylacetylene. In conclusion, this leads us to predict that aryl radicals – upon reaction with allene/methylacetylene – may undergo molecular mass growth processes via ring annulation and de facto addition of a five-membered ring to form molecular building blocks essential to transit planar PAHs out of the plane.

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

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

OSTI ID:: 1603183

Alternate ID(s):: OSTI ID: 1543171; OSTI ID: 1608273

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Vol. 21, Issue 30; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 24 works

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Influence of early stages of triglyceride pyrolysis on the formation of PAHs as coke precursors Kozliak, Evguenii; Sulkes, Mark; Alhroub, Ibrahim Physical Chemistry Chemical Physics, Vol. 21, Issue 36 https://doi.org/10.1039/c9cp02025j	journal	January 2019

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