Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way

Zhao, Long; Prendergast, Matthew B.; Kaiser, Ralf I.; Xu, Bo; Ablikim, Utuq; Ahmed, Musahid; Sun, Bing‐Jian; Chen, Yue‐Lin; Chang, Agnes H.  H.; Mohamed, Rana K.; Fischer, Felix R.

doi:10.1002/anie.201909876

Title: Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way

Journal Article · Wed Sep 04 00:00:00 EDT 2019 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201909876· OSTI ID:1603229

^[1];

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

^[2];

^[2]; Sun, Bing‐Jian ^[3]; Chen, Yue‐Lin ^[3]; Chang, Agnes H. H. ^[3]; Mohamed, Rana K. ^[4]; Fischer, Felix R. ^[5]

Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
National Dong Hwa Univ. (Taiwan)
Univ. of Hawaii at Manoa, Honolulu, HI (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)

Polycyclic aromatic hydrocarbons (PAHs) represent the link between resonance-stabilized free radicals and carbonaceous nanoparticles generated in incomplete combustion processes and in circumstellar envelopes of carbon rich asymptotic giant branch (AGB) stars. While these PAHs resemble building blocks of complex carbonaceous nanostructures, their fundamental formation mechanisms have remained elusive. By investigating these reaction mechanisms of the phenyl radical with biphenyl/naphthalene theoretically and experimentally, we provide compelling evidence on a novel phenyl-addition/dehydrocyclization (PAC) pathway leading to prototype PAHs: triphenylene and fluoranthene. PAC operates efficiently at high temperatures leading through rapid molecular mass growth processes to complex aromatic structures, which are difficult to synthesize by traditional pathways such as hydrogen-abstraction/acetylene-addition. The elucidation of the fundamental reactions leading to PAHs is necessary to facilitate an understanding of the origin and evolution of the molecular universe and of carbon in our galaxy.

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Research Organization:: Univ. of Hawaii, Honolulu, HI (United States); University of California, Berkeley, CA (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

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

OSTI ID:: 1603229

Alternate ID(s):: OSTI ID: 1570522; OSTI ID: 1608275

Journal Information:: Angewandte Chemie (International Edition), Vol. 58, Issue 48; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 40 works

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Low-temperature Formation of Carbonaceous Dust Grains from PAHs Gavilan Marin, Lisseth; Bejaoui, Salma; Haggmark, Michael The Astrophysical Journal, Vol. 889, Issue 2 https://doi.org/10.3847/1538-4357/ab62b7	journal	January 2020

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Title: Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way

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