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Title: VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C 10H 8)

Abstract

The formation of the simplest polycyclic aromatic hydrocarbon (PAH), naphthalene (C 10H 8), was explored in a high-temperature chemical reactor under combustion-like conditions in the phenyl (C 6H 5)-vinylacetylene (C 4H 4) system. The products were probed utilizing tunable vacuum ultraviolet light by scanning the photoionization efficiency (PIE) curve at a mass-to-charge m/z = 128 (C 10H 8 +) of molecules entrained in a molecular beam. The data fitting with PIE reference curves of naphthalene, 4-phenylvinylacetylene (C 6H 5CCC 2H 3), and trans-1-phenylvinylacetylene (C 6H 5CHCHCCH) indicates that the isomers were generated with branching ratios of 43.5±9.0: 6.5±1.0: 50.0±10.0%. Kinetics simulations agree nicely with the experimental findings with naphthalene synthesized via the hydrogen abstraction-vinylacetylene addition (HAVA) pathway and through hydrogen-assisted isomerization of phenylvinylacetylenes. In conclusion, the HAVA route to naphthalene at elevated temperatures represents an alternative pathway to the hydrogen abstraction-acetylene addition (HACA) forming naphthalene in flames and circumstellar envelopes, whereas in cold molecular clouds, HAVA synthesizes naphthalene via a barrierless bimolecular route.

Authors:
 [1]; ORCiD logo [1]; ORCiD logo [2];  [2];  [2];  [3];  [3];  [4]; ORCiD logo [4]; ORCiD logo [5]
  1. Univ. of Hawaii at Manoa, Honolulu, HI (United States). Dept. of Chemistry
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Div.
  3. Samara National Research Univ., Samara (Russian Federation); Lebedev Physical Institute, Samara (Russian Federation)
  4. Florida International Univ., Miami, FL (United States). Dept of Chemistry and Biochemistry
  5. Florida International Univ., Miami, FL (United States). Dept of Chemistry and Biochemistry; Samara National Research Univ., Samara (Russian Federation)
Publication Date:
Research Org.:
Univ. of Hawaii at Manoa, Honolulu, HI (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1603087
Alternate Identifier(s):
OSTI ID: 1459406
Grant/Contract Number:  
FG02-03ER15411; AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry Letters
Additional Journal Information:
Journal Volume: 9; Journal Issue: 10; Journal ID: ISSN 1948-7185
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Zagidullin, Marsel V., Azyazov, Valeriy N., Howlader, A. Hasan, Wnuk, Stanislaw F., and Mebel, Alexander M. VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C10H8). United States: N. p., 2018. Web. doi:10.1021/acs.jpclett.8b01020.
Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Zagidullin, Marsel V., Azyazov, Valeriy N., Howlader, A. Hasan, Wnuk, Stanislaw F., & Mebel, Alexander M. VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C10H8). United States. doi:10.1021/acs.jpclett.8b01020.
Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Ahmed, Musahid, Zagidullin, Marsel V., Azyazov, Valeriy N., Howlader, A. Hasan, Wnuk, Stanislaw F., and Mebel, Alexander M. Wed . "VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C10H8)". United States. doi:10.1021/acs.jpclett.8b01020. https://www.osti.gov/servlets/purl/1603087.
@article{osti_1603087,
title = {VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C10H8)},
author = {Zhao, Long and Kaiser, Ralf I. and Xu, Bo and Ablikim, Utuq and Ahmed, Musahid and Zagidullin, Marsel V. and Azyazov, Valeriy N. and Howlader, A. Hasan and Wnuk, Stanislaw F. and Mebel, Alexander M.},
abstractNote = {The formation of the simplest polycyclic aromatic hydrocarbon (PAH), naphthalene (C10H8), was explored in a high-temperature chemical reactor under combustion-like conditions in the phenyl (C6H5)-vinylacetylene (C4H4) system. The products were probed utilizing tunable vacuum ultraviolet light by scanning the photoionization efficiency (PIE) curve at a mass-to-charge m/z = 128 (C10H8+) of molecules entrained in a molecular beam. The data fitting with PIE reference curves of naphthalene, 4-phenylvinylacetylene (C6H5CCC2H3), and trans-1-phenylvinylacetylene (C6H5CHCHCCH) indicates that the isomers were generated with branching ratios of 43.5±9.0: 6.5±1.0: 50.0±10.0%. Kinetics simulations agree nicely with the experimental findings with naphthalene synthesized via the hydrogen abstraction-vinylacetylene addition (HAVA) pathway and through hydrogen-assisted isomerization of phenylvinylacetylenes. In conclusion, the HAVA route to naphthalene at elevated temperatures represents an alternative pathway to the hydrogen abstraction-acetylene addition (HACA) forming naphthalene in flames and circumstellar envelopes, whereas in cold molecular clouds, HAVA synthesizes naphthalene via a barrierless bimolecular route.},
doi = {10.1021/acs.jpclett.8b01020},
journal = {Journal of Physical Chemistry Letters},
number = 10,
volume = 9,
place = {United States},
year = {2018},
month = {5}
}

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Works referencing / citing this record:

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
  • DOI: 10.1039/c9cp02930c

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
  • DOI: 10.1039/c9cp02930c