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:
-
- Univ. of Hawaii at Manoa, Honolulu, HI (United States)
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Samara National Research Univ. (Russia)
- Florida Intl Univ., Miami, FL (United States)
- Samara National Research Univ. (Russia); Florida Intl Univ., Miami, FL (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:
- 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.
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
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.
@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}
}
Web of Science
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Polycyclic aromatic hydrocarbon formation chemistry in a plasma jet revealed by IR-UV action spectroscopy
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Low-temperature Formation of Carbonaceous Dust Grains from PAHs
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Polycyclic aromatic hydrocarbon formation chemistry in a plasma jet revealed by IR-UV action spectroscopy
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Multiphoton dissociation dynamics of the indenyl radical at 248 nm and 193 nm
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