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/anie.201913037

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

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 illustrated. 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. Thus, connecting helicene templates to the Origins of Life ultimately changes our hypothesis on interstellar carbon chemistry.

Authors:

^[1];

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

^[2];

^[3];

^[4]

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

Publication Date:: 2019-12-23

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

Sponsoring Org.:: Ministry of Science and Higher Education of the Russian Federation; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

OSTI Identifier:: 1603233

Alternate Identifier(s):: OSTI ID: 1593495; OSTI ID: 1608276

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

Resource Type:: Accepted Manuscript

Journal Name:: Angewandte Chemie (International Edition)

Additional Journal Information:: Journal Name: Angewandte Chemie (International Edition); Journal Volume: 59; Journal Issue: 10; Journal ID: ISSN 1433-7851

Publisher:: Wiley

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; gas-phase chemistry; hydrogen abstraction/vinylacetylene addition (HAVA); interstellar medium; mass spectrometry; polycyclic aromatic hydrocarbons (PAHs)

Citation Formats


                    Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., and Mebel, Alexander M. A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase.  United States: N. p., 2019. 
Web.  doi:10.1002/anie.201913037.

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                    Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., & Mebel, Alexander M. A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase.  United States.  https://doi.org/10.1002/anie.201913037

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                    Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., and Mebel, Alexander M. Mon .  
"A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase".  United States.  https://doi.org/10.1002/anie.201913037.  https://www.osti.gov/servlets/purl/1603233.

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@article{osti_1603233,

  title        = {A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase},

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

  abstractNote = {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 illustrated. 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. Thus, connecting helicene templates to the Origins of Life ultimately changes our hypothesis on interstellar carbon chemistry.},

  doi          = {10.1002/anie.201913037},

  journal      = {Angewandte Chemie (International Edition)},

  number       = 10,

  volume       = 59,

  place        = {United States},

  year         = {2019},

  month        = {12}

}

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

Abstract

Citation Formats

Toward controlled synthesis of carbon nanotubes and graphenes journal, March 2012

Beiträge zur Chemie des Braunkohlentheers journal, June 1899

Polycyclic aromatic hydrocarbons, carbon nanoparticles and the diffuse interstellar bands journal, January 2006

Hydropyrolysis: A new technique for the analysis of macromolecular material in meteorites journal, October 2005

Specification of Molecular Chirality journal, April 1966

The molecular universe journal, July 2013

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On the Formation of Dipeptides in Interstellar Model ices journal, February 2013

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Beiträge zur Chemie des Braunkohlentheers journal, July 1901

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Hydropyrolysis: A new technique for the analysis of macromolecular material in meteorites
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Synthese der isomeren Kohlenwasserstoffe 1, 2?5, 6-Dibenzanthracen und 3, 4?5, 6-Dibenzphenanthren
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Dust destruction in the ISM: a re-evaluation of dust lifetimes
journal, May 2011

Organic compounds in the Forest Vale, H4 ordinary chondrite
journal, July 1992

Synthesis and Characterization of Oxygen-Embedded Quinoidal Pentacene and Nonacene
journal, January 2019

Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures
journal, March 2015

The Infrared Spectrum of Protonated Naphthalene and its Relevance for the Unidentified Infrared Bands
journal, August 2009

Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series
journal, January 1977

Wood-Specific Polycyclic Aromatic Hydrocarbon (PAH) Patterns in Soot Using Gas Chromatography-Atmospheric Pressure Laser Ionization-Mass Spectrometry (GC-APLI-MS)
journal, January 2015

Spezifikation der molekularen Chiralität
journal, April 1966

HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars
journal, March 2017

Formation of Methylamine and Ethylamine in Extraterrestrial Ices and Their Role as Fundamental Building Blocks of Proteinogenic α -amino Acids
journal, August 2017

Ribose and related sugars from ultraviolet irradiation of interstellar ice analogs
journal, April 2016

Pahs and Astrobiology
journal, January 2011

Pyrene-based aggregation-induced emission luminogens and their applications
journal, January 2019

HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars
journal, March 2017

Polycyclic aromatic hydrocarbon processing in interstellar shocks
journal, February 2010

Interstellar Polycyclic Aromatic Hydrocarbon Molecules
journal, September 2008

A vacuum ultraviolet photoionization study on high-temperature decomposition of JP-10 (exo-tetrahydrodicyclopentadiene)
journal, January 2017

Molecular and Isotopic Distributions of PAHs from Three Antarctic Carbonaceous Chondrites (CM2)
journal, January 1998

Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures
journal, March 2015

On the Formation of Dipeptides in Interstellar Model ices
journal, February 2013

Polycyclic Aromatic Hydrocarbons in Particulate Matter Emitted by the Combustion of Diesel and Biodiesel
journal, February 2013

Formation of polycyclic aromatic hydrocarbons in circumstellar envelopes
journal, June 1989

Beiträge zur Chemie des Braunkohlentheers
journal, January 1892

Water acting as a catalyst for electron-driven molecular break-up of tetrahydrofuran
journal, May 2020

Beiträge zur Chemie des Braunkohlentheers
journal, July 1901

The Molecular Universe
journal, June 2011