Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures
Abstract
For the past decades, the hydrogen-abstraction/acetylene-addition (HACA) mechanism has been instrumental in attempting to untangle the origin of polycyclic aromatic hydrocarbons (PAHs) as identified in carbonaceous meteorites such as Allende and Murchison. However, the fundamental reaction mechanisms leading to the synthesis of PAHs beyond phenanthrene (C14H10) are still unknown. By exploring the reaction of the 4-phenanthrenyl radical (C14H9•) with acetylene (C2H2) under conditions prevalent in carbon-rich circumstellar environments, we show evidence of a facile, isomer-selective formation of pyrene (C16H10). Along with the hydrogen-abstraction/vinylacetylene-addition (HAVA) mechanism, molecular mass growth processes from pyrene may lead through systematic ring expansions not only to more complex PAHs, but ultimately to 2D graphene-type structures. These fundamental reaction mechanisms are crucial to facilitate an understanding of the origin and evolution of the molecular universe and, in particular, of carbon in our Galaxy.
- Authors:
-
- Univ. of Hawaii at Manoa, Honolulu, HI (United States). Dept. of Chemistry
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
- Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Sciences Division; Univ. of California, Berkeley, CA (United States). Kavli Energy Nano Sciences Inst.
- Florida International Univ., Miami, FL (United States). Dept. of Chemistry and Biochemistry
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Univ. of Hawaii at Manoa, Honolulu, HI (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division
- OSTI Identifier:
- 1461139
- Alternate Identifier(s):
- OSTI ID: 1603085
- Grant/Contract Number:
- AC02-05CH11231; FG02-03ER15411
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Nature Astronomy
- Additional Journal Information:
- Journal Volume: 2; Journal Issue: 5; Journal ID: ISSN 2397-3366
- Publisher:
- Springer
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 79 ASTRONOMY AND ASTROPHYSICS
Citation Formats
Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Joshi, Dharati, Veber, Gregory, Fischer, Felix R., and Mebel, Alexander M. Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures. United States: N. p., 2018.
Web. doi:10.1038/s41550-018-0399-y.
Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Joshi, Dharati, Veber, Gregory, Fischer, Felix R., & Mebel, Alexander M. Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures. United States. https://doi.org/10.1038/s41550-018-0399-y
Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Joshi, Dharati, Veber, Gregory, Fischer, Felix R., and Mebel, Alexander M. Mon .
"Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures". United States. https://doi.org/10.1038/s41550-018-0399-y. https://www.osti.gov/servlets/purl/1461139.
@article{osti_1461139,
title = {Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures},
author = {Zhao, Long and Kaiser, Ralf I. and Xu, Bo and Ablikim, Utuq and Ahmed, Musahid and Joshi, Dharati and Veber, Gregory and Fischer, Felix R. and Mebel, Alexander M.},
abstractNote = {For the past decades, the hydrogen-abstraction/acetylene-addition (HACA) mechanism has been instrumental in attempting to untangle the origin of polycyclic aromatic hydrocarbons (PAHs) as identified in carbonaceous meteorites such as Allende and Murchison. However, the fundamental reaction mechanisms leading to the synthesis of PAHs beyond phenanthrene (C14H10) are still unknown. By exploring the reaction of the 4-phenanthrenyl radical (C14H9•) with acetylene (C2H2) under conditions prevalent in carbon-rich circumstellar environments, we show evidence of a facile, isomer-selective formation of pyrene (C16H10). Along with the hydrogen-abstraction/vinylacetylene-addition (HAVA) mechanism, molecular mass growth processes from pyrene may lead through systematic ring expansions not only to more complex PAHs, but ultimately to 2D graphene-type structures. These fundamental reaction mechanisms are crucial to facilitate an understanding of the origin and evolution of the molecular universe and, in particular, of carbon in our Galaxy.},
doi = {10.1038/s41550-018-0399-y},
journal = {Nature Astronomy},
number = 5,
volume = 2,
place = {United States},
year = {Mon Mar 05 00:00:00 EST 2018},
month = {Mon Mar 05 00:00:00 EST 2018}
}
Web of Science
Figures / Tables:
Works referenced in this record:
Application of Two-Step Laser Mass Spectrometry to Cosmogeochemistry: Direct Analysis of Meteorites
journal, March 1988
- Hahn, J. H.; Zenobi, R.; Bada, J. L.
- Science, Vol. 239, Issue 4847
Mid-infrared spectra of WC 9 stars - The composition of circumstellar and interstellar dust
journal, September 1989
- Cohen, M.; Tielens, A. G. G. M.; Bregman, J. D.
- The Astrophysical Journal, Vol. 344
Kinetic modeling of soot formation with detailed chemistry and physics: laminar premixed flames of C2 hydrocarbons
journal, April 2000
- Appel, Jörg; Bockhorn, Henning; Frenklach, Michael
- Combustion and Flame, Vol. 121, Issue 1-2
The molecular universe
journal, July 2013
- Tielens, A. G. G. M.
- Reviews of Modern Physics, Vol. 85, Issue 3
Chemical Evolution of Carbonaceous Material in Interstellar Clouds
journal, January 2000
- Duley, W. W.
- The Astrophysical Journal, Vol. 528, Issue 2
Hydrogen Abstraction/Acetylene Addition Revealed
journal, June 2014
- Parker, Dorian S. N.; Kaiser, Ralf I.; Troy, Tyler P.
- Angewandte Chemie, Vol. 126, Issue 30
Reaction of Phenyl Radicals with Acetylene: Quantum Chemical Investigation of the Mechanism and Master Equation Analysis of the Kinetics
journal, September 2003
- Tokmakov, I. V.; Lin, M. C.
- Journal of the American Chemical Society, Vol. 125, Issue 37
Detection of C60 and C70 in a Young Planetary Nebula
journal, July 2010
- Cami, J.; Bernard-Salas, J.; Peeters, E.
- Science, Vol. 329, Issue 5996
The Infrared Spectrum of Protonated Naphthalene and its Relevance for the Unidentified Infrared Bands
journal, August 2009
- Ricks, Allen M.; Douberly, Gary E.; Duncan, Michael A.
- The Astrophysical Journal, Vol. 702, Issue 1
Isotopic compositions of individual polycyclic aromatic hydrocarbons from the Murchison meteorite
journal, July 1994
- Gilmour, I.; Pillinger, C. T.
- Monthly Notices of the Royal Astronomical Society, Vol. 269, Issue 2
Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures
journal, March 2015
- Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit
- Angewandte Chemie, Vol. 127, Issue 18
UV Irradiation of Polycyclic Aromatic Hydrocarbons in Ices: Production of Alcohols, Quinones, and Ethers
journal, February 1999
- Bernstein, M. P.
- Science, Vol. 283, Issue 5405
The Molecular Universe
journal, June 2011
- Tielens, A. G. G. M.
- Proceedings of the International Astronomical Union, Vol. 7, Issue S280
Low temperature formation of naphthalene and its role in the synthesis of PAHs (Polycyclic Aromatic Hydrocarbons) in the interstellar medium
journal, December 2011
- Parker, D. S. N.; Zhang, F.; Kim, Y. S.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 1
HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars
journal, March 2017
- Yang, Tao; Kaiser, Ralf I.; Troy, Tyler P.
- Angewandte Chemie, Vol. 129, Issue 16
Nucleation of soot: Molecular dynamics simulations of pyrene dimerization
journal, January 2002
- Schuetz, Charles A.; Frenklach, Michael
- Proceedings of the Combustion Institute, Vol. 29, Issue 2
Polycyclic aromatic hydrocarbon formation in carbon-rich stellar envelopes
journal, December 1992
- Cherchneff, Isabelle; Barker, John R.; Tielens, Alexander G. G. M.
- The Astrophysical Journal, Vol. 401
HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars
journal, March 2017
- Yang, Tao; Kaiser, Ralf I.; Troy, Tyler P.
- Angewandte Chemie International Edition, Vol. 56, Issue 16
Formation pathways of ethynyl-substituted and cyclopenta-fused polycyclic aromatic hydrocarbons
journal, January 2000
- Marsh, Nathan D.; Wornat, Mary J.
- Proceedings of the Combustion Institute, Vol. 28, Issue 2
Interstellar graphite in meteorites: Isotopic compositions and structural properties of single graphite grains from Murchison
journal, March 1995
- Zinner, Ernst; Amari, Sachiko; Wopenka, Brigitte
- Meteoritics, Vol. 30, Issue 2
Interstellar polycyclic aromatic hydrocarbons - The infrared emission bands, the excitation/emission mechanism, and the astrophysical implications
journal, September 1989
- Allamandola, L. J.; Tielens, G. G. M.; Barker, J. R.
- The Astrophysical Journal Supplement Series, Vol. 71
Charged polycyclic aromatic hydrocarbon clusters and the galactic extended red emission
journal, March 2007
- Rhee, Y. M.; Lee, T. J.; Gudipati, M. S.
- Proceedings of the National Academy of Sciences, Vol. 104, Issue 13
Spectroscopic properties of polycyclic aromatic hydrocarbons (PAHs) and astrophysical implications
journal, January 1997
- d'Hendecourt, L.; Ehrenfreund, P.
- Advances in Space Research, Vol. 19, Issue 7
Alkylation of polycyclic aromatic hydrocarbons in carbonaceous chondrites
journal, March 2005
- Elsila, Jamie E.; de Leon, Nathalie P.; Buseck, Peter R.
- Geochimica et Cosmochimica Acta, Vol. 69, Issue 5
Formation of polycyclic aromatic hydrocarbons in circumstellar envelopes
journal, June 1989
- Frenklach, Michael; Feigelson, Eric D.
- The Astrophysical Journal, Vol. 341
Calculations of Rate Coefficients for the Chemically Activated Reactions of Acetylene with Vinylic and Aromatic Radicals
journal, November 1994
- Wang, Hai; Frenklach, Michael
- The Journal of Physical Chemistry, Vol. 98, Issue 44
Evidence that polycyclic aromatic hydrocarbons in two carbonaceous chondrites predate parent-body formation
journal, April 2003
- Plows, Fiona L.; Elsila, Jamie E.; Zare, Richard N.
- Geochimica et Cosmochimica Acta, Vol. 67, Issue 7
Polycyclic aromatic hydrocarbons, carbon nanoparticles and the diffuse interstellar bands
journal, January 2006
- Duley, W. W.
- Faraday Discussions, Vol. 133
Indigenous Polycyclic Aromatic Hydrocarbons in Circumstellar Graphite Grains from Primitive Meteorites
journal, July 1998
- Messenger, S.; Amari, S.; Gao, X.
- The Astrophysical Journal, Vol. 502, Issue 1
Polycyclic Aromatic Hydrocarbons and the Diffuse Interstellar Bands: A Survey
journal, November 1999
- Salama, F.; Galazutdinov, G. A.; Krełowski, J.
- The Astrophysical Journal, Vol. 526, Issue 1
Reaction mechanism of soot formation in flames
journal, February 2002
- Frenklach, Michael
- Physical Chemistry Chemical Physics, Vol. 4, Issue 11
Isotopic evidence from an Antarctic carbonaceous chondrite for two reaction pathways of extraterrestrial PAH formation
journal, December 2000
- Naraoka, Hiroshi; Shimoyama, Akira; Harada, Kaoru
- Earth and Planetary Science Letters, Vol. 184, Issue 1
In Situ Discovery of Graphite with Interstellar Isotopic Signatures in a Chondrule-Free Clast in an L3 Chondrite
journal, May 1998
- Mostefaoui, S.
- Science, Vol. 280, Issue 5368
Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry
journal, January 2013
- Qi, Fei
- Proceedings of the Combustion Institute, Vol. 34, Issue 1
Formation of the diphenyl molecule in the crossed beam reaction of phenyl radicals with benzene
journal, February 2008
- Zhang, Fangtong; Gu, Xibin; Kaiser, Ralf I.
- The Journal of Chemical Physics, Vol. 128, Issue 8
Spatially Resolved Organic Analysis of the Allende Meteorite
journal, November 1989
- Zenobi, R.; Philippoz, J. -M.; Zare, R. N.
- Science, Vol. 246, Issue 4933
Nanosized carbon-rich grains in carbonaceous chondrite meteorites
journal, August 2004
- Garvie, Laurence A. J.; Buseck, Peter R.
- Earth and Planetary Science Letters, Vol. 224, Issue 3-4
Serpentine nanotubes in the Mighei CM chondrite
journal, June 2004
- Zega, T.
- Earth and Planetary Science Letters, Vol. 223, Issue 1-2
Isomeric identification of polycyclic aromatic hydrocarbons formed in combustion with tunable vacuum ultraviolet photoionization
journal, August 2006
- Qi, Fei; Yang, Rui; Yang, Bin
- Review of Scientific Instruments, Vol. 77, Issue 8
Interstellar grains in meteorites: III. Graphite and its noble gases
journal, April 1995
- Amari, Sachiko; Lewis, Roy S.; Anders, Edward
- Geochimica et Cosmochimica Acta, Vol. 59, Issue 7
Exploring the Role of PAHs in the Formation of Soot: Pyrene Dimerization
journal, September 2010
- Sabbah, Hassan; Biennier, Ludovic; Klippenstein, Stephen J.
- The Journal of Physical Chemistry Letters, Vol. 1, Issue 19
Formation of polycyclic aromatic hydrocarbons and their growth to soot—a review of chemical reaction pathways
journal, August 2000
- Richter, H.; Howard, J. B.
- Progress in Energy and Combustion Science, Vol. 26, Issue 4-6
Reformulation and Solution of the Master Equation for Multiple-Well Chemical Reactions
journal, May 2013
- Georgievskii, Yuri; Miller, James A.; Burke, Michael P.
- The Journal of Physical Chemistry A, Vol. 117, Issue 46
Flash pyrolytic production of rotationally cold free radicals in a supersonic jet. Resonant multiphoton spectrum of the 3p2A2" .rarw. X2A2" origin band of methyl
journal, May 1986
- Chen, Peter; Colson, Steven D.; Chupka, William A.
- The Journal of Physical Chemistry, Vol. 90, Issue 11
Resonant multiphoton ionization spectrum and electronic structure of CH radical. New states and assignments above 50 000 cm − 1
journal, January 1987
- Chen, Peter; Pallix, Joan B.; Chupka, William A.
- The Journal of Chemical Physics, Vol. 86, Issue 2
Formation Mechanism of Polycyclic Aromatic Hydrocarbons beyond the Second Aromatic Ring
journal, May 2013
- Kislov, V. V.; Sadovnikov, A. I.; Mebel, A. M.
- The Journal of Physical Chemistry A, Vol. 117, Issue 23
Hydrogen Abstraction/Acetylene Addition Revealed
journal, June 2014
- Parker, Dorian S. N.; Kaiser, Ralf I.; Troy, Tyler P.
- Angewandte Chemie International Edition, Vol. 53, Issue 30
Formation Mechanisms of Naphthalene and Indene: From the Interstellar Medium to Combustion Flames
journal, January 2017
- Mebel, Alexander M.; Landera, Alexander; Kaiser, Ralf I.
- The Journal of Physical Chemistry A, Vol. 121, Issue 5
Polycyclic aromatic hydrocarbon processing in interstellar shocks
journal, February 2010
- Micelotta, E. R.; Jones, A. P.; Tielens, A. G. G. M.
- Astronomy and Astrophysics, Vol. 510
Interstellar Polycyclic Aromatic Hydrocarbon Molecules
journal, September 2008
- Tielens, A. G. G. M.
- Annual Review of Astronomy and Astrophysics, Vol. 46, Issue 1
Molecular and Isotopic Distributions of PAHs from Three Antarctic Carbonaceous Chondrites (CM2)
journal, January 1998
- Naraoka, H.
- Mineralogical Magazine, Vol. 62A, Issue 2
Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures
journal, March 2015
- Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit
- Angewandte Chemie International Edition, Vol. 54, Issue 18
Selective detection of isomers with photoionization mass spectrometry for studies of hydrocarbon flame chemistry
journal, October 2003
- Cool, Terrill A.; Nakajima, Koichi; Mostefaoui, Toufik A.
- The Journal of Chemical Physics, Vol. 119, Issue 16
Gaussian-3 (G3) theory for molecules containing first and second-row atoms
journal, November 1998
- Curtiss, Larry A.; Raghavachari, Krishnan; Redfern, Paul C.
- The Journal of Chemical Physics, Vol. 109, Issue 18
Gaussian-3 theory using density functional geometries and zero-point energies
journal, April 1999
- Baboul, Anwar G.; Curtiss, Larry A.; Redfern, Paul C.
- The Journal of Chemical Physics, Vol. 110, Issue 16
NOx and PAHs removal from industrial flue gas by using electron beam technology with alcohol addition
journal, June 2003
- Chmielewski, A. G.; Sun, Yong-Xia; Licki, J.
- Radiation Physics and Chemistry, Vol. 67, Issue 3-4
Water acting as a catalyst for electron-driven molecular break-up of tetrahydrofuran
journal, May 2020
- Wang, Enliang; Ren, Xueguang; Baek, WoonYong
- Nature Communications, Vol. 11, Issue 1
Interstellar and Circumstellar PAHs
journal, January 2000
- Tielens, A. G. G. M.; van Kerckhoven, C.; Peeters, E.
- Symposium - International Astronomical Union, Vol. 197
Works referencing / citing this record:
Gas phase synthesis of [4]-helicene
journal, April 2019
- Zhao, Long; Kaiser, Ralf I.; Xu, Bo
- Nature Communications, Vol. 10, Issue 1
Low-temperature Formation of Carbonaceous Dust Grains from PAHs
journal, January 2020
- Gavilan Marin, Lisseth; Bejaoui, Salma; Haggmark, Michael
- The Astrophysical Journal, Vol. 889, Issue 2
Molecular mass growth through ring expansion in polycyclic aromatic hydrocarbons via radical–radical reactions
journal, August 2019
- Zhao, Long; Kaiser, Ralf. I.; Lu, Wenchao
- Nature Communications, Vol. 10, Issue 1
Prevalence of non-aromatic carbonaceous molecules in the inner regions of circumstellar envelopes
journal, October 2019
- Martínez, Lidia; Santoro, Gonzalo; Merino, Pablo
- Nature Astronomy, Vol. 4, Issue 1
How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C 10 H 7 ) to benzindenes (C 13 H 10 ) as a case study
journal, January 2019
- Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I.
- Physical Chemistry Chemical Physics, Vol. 21, Issue 30
From atoms to aerosols: probing clusters and nanoparticles with synchrotron based mass spectrometry and X-ray spectroscopy
journal, January 2020
- Ahmed, Musahid; Kostko, Oleg
- Physical Chemistry Chemical Physics, Vol. 22, Issue 5
Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way
journal, November 2019
- Zhao, Long; Prendergast, Matthew B.; Kaiser, Ralf I.
- Angewandte Chemie, Vol. 131, Issue 48
Gas‐Phase Synthesis of Triphenylene (C 18 H 12 )
journal, February 2019
- Zhao, Long; Xu, Bo; Ablikim, Utuq
- ChemPhysChem, Vol. 20, Issue 6
Molecular mass growth through ring expansion in polycyclic aromatic hydrocarbons via radical–radical reactions
journal, August 2019
- Zhao, Long; Kaiser, Ralf. I.; Lu, Wenchao
- Nature Communications, Vol. 10, Issue 1
Gas‐Phase Synthesis of Triphenylene (C 18 H 12 )
journal, March 2019
- Zhao, Long; Xu, Bo; Ablikim, Utuq
- ChemPhysChem, Vol. 20, Issue 6
Nitrogen matters: the difference between PANH and PAH formation
journal, January 2018
- Bouwman, Jordy; Bodi, Andras; Hemberger, Patrick
- Physical Chemistry Chemical Physics, Vol. 20, Issue 47
Synthesizing carbon nanotubes in space
journal, October 2019
- Chen, Tao; Li, Aigen
- Astronomy & Astrophysics, Vol. 631
Gas phase synthesis of [4]-helicene
journal, April 2019
- Zhao, Long; Kaiser, Ralf I.; Xu, Bo
- Nature Communications, Vol. 10, Issue 1
Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition-Dehydrocyclization: The Third Way
journal, October 2019
- Zhao, Long; Prendergast, Matthew B.; Kaiser, Ralf I.
- Angewandte Chemie International Edition, Vol. 58, Issue 48
A combined experimental and computational study on the reaction dynamics of the 1-propynyl radical (CH 3 CC; X 2 A 1 ) with ethylene (H 2 CCH 2 ; X 1 A 1g ) and the formation of 1-penten-3-yne (CH 2 CHCCCH 3 ; X 1 A′)
journal, January 2019
- He, Chao; Zhao, Long; Thomas, Aaron M.
- Physical Chemistry Chemical Physics, Vol. 21, Issue 40
Reactivity of the Indenyl Radical (C 9 H 7 ) with Acetylene (C 2 H 2 ) and Vinylacetylene (C 4 H 4 )
journal, April 2019
- Zhao, Long; Prendergast, Matthew B.; Kaiser, Ralf. I.
- ChemPhysChem
Figures / Tables found in this record: