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

Abstract

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.

Authors:

^[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)

Publication Date:: Wed Sep 04 00:00:00 EDT 2019

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

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

OSTI Identifier:: 1603229

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

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

Resource Type:: Accepted Manuscript

Journal Name:: Angewandte Chemie (International Edition)

Additional Journal Information:: Journal Name: Angewandte Chemie (International Edition); Journal Volume: 58; Journal Issue: 48; 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; interstellar medium; mass spectrometry; phenyl-addition/dehydrocyclization (PAC); polycyclic aromatic hydrocarbons

Citation Formats


                    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., and Fischer, Felix R. Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way.  United States: N. p., 2019. 
Web.  doi:10.1002/anie.201909876.

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                    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. Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way.  United States.  https://doi.org/10.1002/anie.201909876

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                    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., and Fischer, Felix R. Wed .  
"Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way".  United States.  https://doi.org/10.1002/anie.201909876.  https://www.osti.gov/servlets/purl/1603229.

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@article{osti_1603229,

  title        = {Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way},

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

  abstractNote = {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.},

  doi          = {10.1002/anie.201909876},

  journal      = {Angewandte Chemie (International Edition)},

  number       = 48,

  volume       = 58,

  place        = {United States},

  year         = {Wed Sep 04 00:00:00 EDT 2019},

  month        = {Wed Sep 04 00:00:00 EDT 2019}

}

Copy to clipboard

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Works referencing / citing this record:

Low-temperature Formation of Carbonaceous Dust Grains from PAHs
journal, January 2020

Gavilan Marin, Lisseth; Bejaoui, Salma; Haggmark, Michael
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Title: Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way

Abstract

Citation Formats

Perturbative corrections to account for triple excitations in closed and open shell coupled cluster theories journal, September 1994

Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures journal, March 2018

Interstellar Chemistry: A Strategy for Detecting Polycyclic Aromatic Hydrocarbons in Space journal, March 2005

Kinetic modeling study of benzene and PAH formation in laminar methane flames journal, May 2015

Evaluated Kinetic Data for Combustion Modelling journal, May 1992

Synthesis of urea in cometary model ices and implications for Comet 67P/Churyumov–Gerasimenko journal, January 2016

A VUV Photoionization Study of the Formation of the Indene Molecule and Its Isomers journal, June 2011

Density‐functional thermochemistry. II. The effect of the Perdew–Wang generalized‐gradient correlation correction journal, December 1992

Physical properties of fullerene-containing Galactic planetary nebulae journal, December 2013

Resonance-stabilized hydrocarbon-radical chain reactions may explain soot inception and growth journal, September 2018

The molecular universe journal, July 2013

Low-temperature formation of polycyclic aromatic hydrocarbons in Titan’s atmosphere journal, October 2018

Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry journal, January 2013

Hydrogen Abstraction/Acetylene Addition Revealed journal, June 2014

Coupled cluster theory for high spin, open shell reference wave functions journal, October 1993

A full coupled‐cluster singles and doubles model: The inclusion of disconnected triples journal, February 1982

Detection of Buckminsterfullerene in Usual Soots and Commercial Charcoals journal, March 1999

Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons journal, June 1974

XXX.—A rule for determining whether a given benzene mono-derivative shall give a meta-di-derivative or a mixture of ortho- and para-di-derivatives journal, January 1892

Hydrogen-Abstraction/Acetylene-Addition Exposed journal, October 2016

Kinetic study of the formation of triphenylene from the condensation of C12H10+C6H5 journal, April 2012

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

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

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

Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction journal, February 1992

Hydrogen Abstraction/Acetylene Addition Revealed journal, June 2014

Time-Dependent Mass Spectra and Breakdown Graphs. 19. Fluoranthene journal, July 1995

VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C 10 H 8 ) journal, May 2018

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

Role of Phenyl Radicals in the Growth of Polycyclic Aromatic Hydrocarbons journal, March 2008

Interstellar Polycyclic Aromatic Hydrocarbon Molecules journal, September 2008

Hydrogen-Abstraction/Acetylene-Addition Exposed journal, October 2016

Charged polycyclic aromatic hydrocarbon clusters and the galactic extended red emission journal, March 2007

A detailed kinetic modeling study of aromatics formation in laminar premixed acetylene and ethylene flames journal, July 1997

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

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

Photoelectron spectra of p-terphenyl in gaseous and solid states journal, November 1975

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

Physical Properties of Fullerene-containing Galactic Planetary Nebulae conference, June 2014

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density text, January 1988

The Molecular Universe journal, June 2011

Low-temperature Formation of Carbonaceous Dust Grains from PAHs journal, January 2020

Perturbative corrections to account for triple excitations in closed and open shell coupled cluster theories
journal, September 1994

Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures
journal, March 2018

Interstellar Chemistry: A Strategy for Detecting Polycyclic Aromatic Hydrocarbons in Space
journal, March 2005

Kinetic modeling study of benzene and PAH formation in laminar methane flames
journal, May 2015

Evaluated Kinetic Data for Combustion Modelling
journal, May 1992

Synthesis of urea in cometary model ices and implications for Comet 67P/Churyumov–Gerasimenko
journal, January 2016

A VUV Photoionization Study of the Formation of the Indene Molecule and Its Isomers
journal, June 2011

Density‐functional thermochemistry. II. The effect of the Perdew–Wang generalized‐gradient correlation correction
journal, December 1992

Physical properties of fullerene-containing Galactic planetary nebulae
journal, December 2013

Resonance-stabilized hydrocarbon-radical chain reactions may explain soot inception and growth
journal, September 2018

The molecular universe
journal, July 2013

Low-temperature formation of polycyclic aromatic hydrocarbons in Titan’s atmosphere
journal, October 2018

Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry
journal, January 2013

Hydrogen Abstraction/Acetylene Addition Revealed
journal, June 2014

Coupled cluster theory for high spin, open shell reference wave functions
journal, October 1993

A full coupled‐cluster singles and doubles model: The inclusion of disconnected triples
journal, February 1982

Detection of Buckminsterfullerene in Usual Soots and Commercial Charcoals
journal, March 1999

Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons
journal, June 1974

XXX.—A rule for determining whether a given benzene mono-derivative shall give a meta-di-derivative or a mixture of ortho- and para-di-derivatives
journal, January 1892

Hydrogen-Abstraction/Acetylene-Addition Exposed
journal, October 2016

Kinetic study of the formation of triphenylene from the condensation of C12H10+C6H5
journal, April 2012

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

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

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

Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction
journal, February 1992

Hydrogen Abstraction/Acetylene Addition Revealed
journal, June 2014

Time-Dependent Mass Spectra and Breakdown Graphs. 19. Fluoranthene
journal, July 1995

VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C ₁₀ H ₈ )
journal, May 2018

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

Role of Phenyl Radicals in the Growth of Polycyclic Aromatic Hydrocarbons
journal, March 2008

Interstellar Polycyclic Aromatic Hydrocarbon Molecules
journal, September 2008

Hydrogen-Abstraction/Acetylene-Addition Exposed
journal, October 2016

Charged polycyclic aromatic hydrocarbon clusters and the galactic extended red emission
journal, March 2007

A detailed kinetic modeling study of aromatics formation in laminar premixed acetylene and ethylene flames
journal, July 1997

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

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

Photoelectron spectra of p-terphenyl in gaseous and solid states
journal, November 1975

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

Physical Properties of Fullerene-containing Galactic Planetary Nebulae
conference, June 2014

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
text, January 1988

The Molecular Universe
journal, June 2011

Low-temperature Formation of Carbonaceous Dust Grains from PAHs
journal, January 2020