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Title: Gas phase synthesis of [4]-helicene

Abstract

A synthetic route to racemic helicenes via a vinylacetylene mediated gas phase chemistry involving elementary reactions with aryl radicals is presented. In contrast to traditional synthetic routes involving solution chemistry and ionic reaction intermediates, the gas phase synthesis involves a targeted ring annulation involving free radical intermediates. Exploiting the simplest helicene as a benchmark, we show that the gas phase reaction of the 4-phenanthrenyl radical ([C14H9]•) with vinylacetylene (C4H4) yields [4]-helicene (C18H12) along with atomic hydrogen via a low-barrier mechanism through a resonance-stabilized free radical intermediate (C18H13). This pathway may represent a versatile mechanism to build up even more complex polycyclic aromatic hydrocarbons such as [5]- and [6]-helicene via stepwise ring annulation through bimolecular gas phase reactions in circumstellar envelopes of carbon-rich stars, whereas secondary reactions involving hydrogen atom assisted isomerization of thermodynamically less stable isomers of [4]-helicene might be important in combustion flames as well.

Authors:
 [1]; ORCiD logo [1];  [2];  [2];  [2]; ORCiD logo [2];  [3];  [3];  [3];  [3];  [4];  [4]; ORCiD logo [4];  [5];  [6];  [6];  [7]
+ Show Author Affiliations
  1. Univ. of Hawaii at Manoa, Honolulu, HI (United States)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  3. Samara National Research Univ. (Russia)
  4. Florida Intl Univ., Miami, FL (United States)
  5. Samara National Research Univ. (Russia); Florida Intl Univ., Miami, FL (United States)
  6. Univ. of California, Berkeley, CA (United States)
  7. Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Florida International Univ. (FIU), Miami, FL (United States); Univ. of Hawaii, Honolulu, HI (United States); Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; Ministry of Education and Science of the Russian Federation
OSTI Identifier:
1546667
Alternate Identifier(s):
OSTI ID: 1594767; OSTI ID: 1603093
Grant/Contract Number:  
AC02-05CH11231; FG02-03ER15411; FG02-04ER15570; SC0010409; DEFG02- 03ER15411; 14.Y26.31.0020
Resource Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 10; Journal Issue: 1; Journal ID: ISSN 2041-1723
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 74 ATOMIC AND MOLECULAR PHYSICS

Citation Formats

Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Lu, Wenchao, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., Zagidullin, Marsel V., Morozov, Alexander N., Howlader, A. Hasan, Wnuk, Stanislaw F., Mebel, Alexander M., Joshi, Dharati, Veber, Gregory, and Fischer, Felix R. Gas phase synthesis of [4]-helicene. United States: N. p., 2019. Web. doi:10.1038/s41467-019-09224-8.
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Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Lu, Wenchao, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., Zagidullin, Marsel V., Morozov, Alexander N., Howlader, A. Hasan, Wnuk, Stanislaw F., Mebel, Alexander M., Joshi, Dharati, Veber, Gregory, & Fischer, Felix R. Gas phase synthesis of [4]-helicene. United States. https://doi.org/10.1038/s41467-019-09224-8
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Zhao, Long, Kaiser, Ralf I., Xu, Bo, Ablikim, Utuq, Lu, Wenchao, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., Zagidullin, Marsel V., Morozov, Alexander N., Howlader, A. Hasan, Wnuk, Stanislaw F., Mebel, Alexander M., Joshi, Dharati, Veber, Gregory, and Fischer, Felix R. Wed . "Gas phase synthesis of [4]-helicene". United States. https://doi.org/10.1038/s41467-019-09224-8. https://www.osti.gov/servlets/purl/1546667.
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@article{osti_1546667,
title = {Gas phase synthesis of [4]-helicene},
author = {Zhao, Long and Kaiser, Ralf I. and Xu, Bo and Ablikim, Utuq and Lu, Wenchao and Ahmed, Musahid and Evseev, Mikhail M. and Bashkirov, Eugene K. and Azyazov, Valeriy N. and Zagidullin, Marsel V. and Morozov, Alexander N. and Howlader, A. Hasan and Wnuk, Stanislaw F. and Mebel, Alexander M. and Joshi, Dharati and Veber, Gregory and Fischer, Felix R.},
abstractNote = {A synthetic route to racemic helicenes via a vinylacetylene mediated gas phase chemistry involving elementary reactions with aryl radicals is presented. In contrast to traditional synthetic routes involving solution chemistry and ionic reaction intermediates, the gas phase synthesis involves a targeted ring annulation involving free radical intermediates. Exploiting the simplest helicene as a benchmark, we show that the gas phase reaction of the 4-phenanthrenyl radical ([C14H9]•) with vinylacetylene (C4H4) yields [4]-helicene (C18H12) along with atomic hydrogen via a low-barrier mechanism through a resonance-stabilized free radical intermediate (C18H13). This pathway may represent a versatile mechanism to build up even more complex polycyclic aromatic hydrocarbons such as [5]- and [6]-helicene via stepwise ring annulation through bimolecular gas phase reactions in circumstellar envelopes of carbon-rich stars, whereas secondary reactions involving hydrogen atom assisted isomerization of thermodynamically less stable isomers of [4]-helicene might be important in combustion flames as well.},
doi = {10.1038/s41467-019-09224-8},
journal = {Nature Communications},
number = 1,
volume = 10,
place = {United States},
year = {Wed Apr 03 00:00:00 EDT 2019},
month = {Wed Apr 03 00:00:00 EDT 2019}
}
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https://doi.org/10.1038/s41467-019-09224-8
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Efficient Phenanthrene, Helicene, and Azahelicene Syntheses.
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Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry
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Hydrogen Abstraction Acetylene Addition and Diels−Alder Mechanisms of PAH Formation:  A Detailed Study Using First Principles Calculations
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