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/ange.201909876

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

Journal Article · Wed Sep 04 00:00:00 EDT 2019 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201909876· OSTI ID:1769308

^[1]; ^[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., Shoufeng, Hualien (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); Kavli Energy Nano Sciences Inst., 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. Although these PAHs resemble building blocks of complex carbonaceous nanostructures, their fundamental formation mechanisms have remained elusive. By exploring 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.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)

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

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

OSTI ID:: 1769308

Alternate ID(s):: OSTI ID: 1570540

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 48 Vol. 131; ISSN 0044-8249

Publisher:: German Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Interstellares Medium
Massenspektrometrie
Phenyladdition/-dehydrocyclisierung (PAC)
Polycyclische aromatische Kohlenwasserstoffe

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

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