A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Zhao, Long; Kaiser, Ralf I.; Xu, Bo; Ablikim, Utuq; Ahmed, Musahid; Evseev, Mikhail M.; Bashkirov, Eugene K.; Azyazov, Valeriy N.; Mebel, Alexander M.

doi:10.1002/anie.201913037

Title: A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Journal Article · 22 December 2019 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.201913037 · OSTI ID:1603233

^[1];

^[2]; Xu, Bo ^[3];

^[3];

^[4];

^[5]

Univ. of Hawaii at Manoa, Honolulu, HI (United States); University of Hawaii at Manoa
Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Samara National Research Univ. (Russia)
Samara National Research Univ. (Russia); Florida International Univ., Miami, FL (United States)

A unified low-temperature reaction mechanism on the formation of acenes, phenacenes, and helicenes—polycyclic aromatic hydrocarbons (PAHs) that are distinct via the linear, zigzag, and ortho-condensed arrangements of fused benzene rings—is illustrated. This mechanism is mediated through a barrierless, vinylacetylene mediated gas-phase chemistry utilizing tetracene, [4]phenacene, and [4]helicene as benchmarks contesting established ideas that molecular mass growth processes to PAHs transpire at elevated temperatures. This mechanism opens up an isomer-selective route to aromatic structures involving submerged reaction barriers, resonantly stabilized free-radical intermediates, and systematic ring annulation potentially yielding molecular wires along with racemic mixtures of helicenes in deep space. Thus, connecting helicene templates to the Origins of Life ultimately changes our hypothesis on interstellar carbon chemistry.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Florida International Univ., Miami, FL (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States); Univ. of Hawaii, Honolulu, HI (United States)

Sponsoring Organization:: Ministry of Science and Higher Education of the Russian Federation; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-05CH11231; FG02-03ER15411; FG02-04ER15570

OSTI ID:: 1603233

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 10 Vol. 59; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (39)

Beiträge zur Chemie des Braunkohlentheers Oehler, Eugen Zeitschrift für Angewandte Chemie, Vol. 12, Issue 24 https://doi.org/10.1002/ange.18990122402	journal	June 1899
Beiträge zur Chemie des Braunkohlentheers Rosenthal, Theodor Zeitschrift für Angewandte Chemie, Vol. 14, Issue 27 https://doi.org/10.1002/ange.19010142702	journal	July 1901
Spezifikation der molekularen Chiralität Cahn, R. S.; Ingold, Christopher; Prelog, V. Angewandte Chemie, Vol. 78, Issue 8 https://doi.org/10.1002/ange.19660780803	journal	April 1966
Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit Angewandte Chemie, Vol. 127, Issue 18 https://doi.org/10.1002/ange.201411987	journal	March 2015
HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars Yang, Tao; Kaiser, Ralf I.; Troy, Tyler P. Angewandte Chemie, Vol. 129, Issue 16 https://doi.org/10.1002/ange.201701259	journal	March 2017
Specification of Molecular Chirality Cahn, R. S.; Ingold, Christopher; Prelog, V. Angewandte Chemie International Edition in English, Vol. 5, Issue 4 https://doi.org/10.1002/anie.196603851	journal	April 1966
Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit Angewandte Chemie International Edition, Vol. 54, Issue 18 https://doi.org/10.1002/anie.201411987	journal	March 2015
HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars Yang, Tao; Kaiser, Ralf I.; Troy, Tyler P. Angewandte Chemie International Edition, Vol. 56, Issue 16 https://doi.org/10.1002/anie.201701259	journal	March 2017
Beiträge zur Chemie des Braunkohlentheers Heusler, Fr. Berichte der deutschen chemischen Gesellschaft, Vol. 25, Issue 1 https://doi.org/10.1002/cber.189202501266	journal	January 1892
Synthese der isomeren Kohlenwasserstoffe 1, 2?5, 6-Dibenzanthracen und 3, 4?5, 6-Dibenzphenanthren Weitzenb�ck, Richard; Klingler, Albert Monatshefte f�r Chemie, Vol. 39, Issue 5 https://doi.org/10.1007/BF01524529	journal	May 1918
Organic compounds in the Forest Vale, H4 ordinary chondrite Zenobi, Renato; Philippoz, Jean-Michel; Zare, Richard N. Geochimica et Cosmochimica Acta, Vol. 56, Issue 7 https://doi.org/10.1016/0016-7037(92)90366-Q	journal	July 1992
Isotopic evidence from an Antarctic carbonaceous chondrite for two reaction pathways of extraterrestrial PAH formation Naraoka, Hiroshi; Shimoyama, Akira; Harada, Kaoru Earth and Planetary Science Letters, Vol. 184, Issue 1 https://doi.org/10.1016/S0012-821X(00)00316-2	journal	December 2000
Anthracene and pyrene photolysis kinetics in aqueous, organic, and mixed aqueous-organic phases Grossman, Jarod N.; Stern, Adam P.; Kirich, Makena L. Atmospheric Environment, Vol. 128 https://doi.org/10.1016/j.atmosenv.2015.12.049	journal	March 2016
Quantum interference in polycyclic hydrocarbon molecular wires Walter, Derek; Neuhauser, Daniel; Baer, Roi Chemical Physics, Vol. 299, Issue 1 https://doi.org/10.1016/j.chemphys.2003.12.015	journal	March 2004
Estimation of heats of formation and combustion of coal Kaiho, Mamoru; Kodera, Yoichi; Yamada, Osamu Fuel, Vol. 237 https://doi.org/10.1016/j.fuel.2018.09.022	journal	February 2019
Hydropyrolysis: A new technique for the analysis of macromolecular material in meteorites Sephton, Mark A.; Love, Gordon D.; Meredith, Will Planetary and Space Science, Vol. 53, Issue 12 https://doi.org/10.1016/j.pss.2005.06.008	journal	October 2005
The Molecular Universe Tielens, A. G. G. M. Proceedings of the International Astronomical Union, Vol. 7, Issue S280 https://doi.org/10.1017/s1743921311024823	journal	June 2011
Synthesis and Characterization of Oxygen-Embedded Quinoidal Pentacene and Nonacene Wang, Yanpei; Qiu, Shuhai; Xie, Sheng Journal of the American Chemical Society, Vol. 141, Issue 5 https://doi.org/10.1021/jacs.8b13884	journal	January 2019
Water acting as a catalyst for electron-driven molecular break-up of tetrahydrofuran Wang, Enliang; Ren, Xueguang; Baek, WoonYong Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15958-7	journal	May 2020
Low-temperature formation of polycyclic aromatic hydrocarbons in Titan’s atmosphere Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Astronomy, Vol. 2, Issue 12 https://doi.org/10.1038/s41550-018-0585-y	journal	October 2018
A vacuum ultraviolet photoionization study on high-temperature decomposition of JP-10 (exo-tetrahydrodicyclopentadiene) Zhao, Long; Yang, Tao; Kaiser, Ralf I. Physical Chemistry Chemical Physics, Vol. 19, Issue 24 https://doi.org/10.1039/C7CP01571B	journal	January 2017
Pyrene-based aggregation-induced emission luminogens and their applications Islam, Md. Monarul; Hu, Zhen; Wang, Qingsong Materials Chemistry Frontiers, Vol. 3, Issue 5 https://doi.org/10.1039/C9QM00090A	journal	January 2019
Reaction mechanism of soot formation in flames Frenklach, Michael Physical Chemistry Chemical Physics, Vol. 4, Issue 11 https://doi.org/10.1039/b110045a	journal	February 2002
Polycyclic aromatic hydrocarbons, carbon nanoparticles and the diffuse interstellar bands Duley, W. W. Faraday Discussions, Vol. 133 https://doi.org/10.1039/b516323d	journal	January 2006
Polycyclic aromatic hydrocarbon processing in interstellar shocks Micelotta, E. R.; Jones, A. P.; Tielens, A. G. G. M. Astronomy and Astrophysics, Vol. 510 https://doi.org/10.1051/0004-6361/200911682	journal	February 2010
Dust destruction in the ISM: a re-evaluation of dust lifetimes Jones, A. P.; Nuth, J. A. Astronomy & Astrophysics, Vol. 530 https://doi.org/10.1051/0004-6361/201014440	journal	May 2011
Pahs and Astrobiology Allamandola, L. J. EAS Publications Series, Vol. 46 https://doi.org/10.1051/eas/1146032	journal	January 2011
Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series Schmidt, W. The Journal of Chemical Physics, Vol. 66, Issue 2 https://doi.org/10.1063/1.433961	journal	January 1977
Polycyclic Aromatic Hydrocarbons in Particulate Matter Emitted by the Combustion of Diesel and Biodiesel Valle-Hernández, Brenda L.; Amador-Muñoz, Omar; Jazcilevich-Diamant, Aron Combustion Science and Technology, Vol. 185, Issue 3 https://doi.org/10.1080/00102202.2012.726665	journal	February 2013
Wood-Specific Polycyclic Aromatic Hydrocarbon (PAH) Patterns in Soot Using Gas Chromatography-Atmospheric Pressure Laser Ionization-Mass Spectrometry (GC-APLI-MS) Achten, Christine; Beer, Fokko Tjark; Stader, Christian Environmental Forensics, Vol. 16, Issue 1 https://doi.org/10.1080/15275922.2014.991004	journal	January 2015
Formation of polycyclic aromatic hydrocarbons in circumstellar envelopes Frenklach, Michael; Feigelson, Eric D. The Astrophysical Journal, Vol. 341 https://doi.org/10.1086/167501	journal	June 1989
The Infrared Spectrum of Protonated Naphthalene and its Relevance for the Unidentified Infrared Bands Ricks, Allen M.; Douberly, Gary E.; Duncan, Michael A. The Astrophysical Journal, Vol. 702, Issue 1 https://doi.org/10.1088/0004-637X/702/1/301	journal	August 2009
On the Formation of Dipeptides in Interstellar Model ices Kaiser, R. I.; Stockton, A. M.; Kim, Y. S. The Astrophysical Journal, Vol. 765, Issue 2 https://doi.org/10.1088/0004-637X/765/2/111	journal	February 2013
The molecular universe Tielens, A. G. G. M. Reviews of Modern Physics, Vol. 85, Issue 3 https://doi.org/10.1103/RevModPhys.85.1021	journal	July 2013
Ribose and related sugars from ultraviolet irradiation of interstellar ice analogs Meinert, C.; Myrgorodska, I.; de Marcellus, P. Science, Vol. 352, Issue 6282 https://doi.org/10.1126/science.aad8137	journal	April 2016
Interstellar Polycyclic Aromatic Hydrocarbon Molecules Tielens, A. G. G. M. Annual Review of Astronomy and Astrophysics, Vol. 46, Issue 1 https://doi.org/10.1146/annurev.astro.46.060407.145211	journal	September 2008
Molecular and Isotopic Distributions of PAHs from Three Antarctic Carbonaceous Chondrites (CM2) Naraoka, H. Mineralogical Magazine, Vol. 62A, Issue 2 https://doi.org/10.1180/minmag.1998.62A.2.219	journal	January 1998
Toward controlled synthesis of carbon nanotubes and graphenes Itami, Kenichiro Pure and Applied Chemistry, Vol. 84, Issue 4 https://doi.org/10.1351/PAC-CON-11-11-15	journal	March 2012
Formation of Methylamine and Ethylamine in Extraterrestrial Ices and Their Role as Fundamental Building Blocks of Proteinogenic α -amino Acids Förstel, Marko; Bergantini, Alexandre; Maksyutenko, Pavlo The Astrophysical Journal, Vol. 845, Issue 1 https://doi.org/10.3847/1538-4357/aa7edd	journal	August 2017

Similar Records

A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Journal Article · 2020 · Angewandte Chemie · OSTI ID:1593502

Zhao, Long; Kaiser, Ralf I.; Xu, Bo; +6 more

A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene

Journal Article · 2020 · Angewandte Chemie · OSTI ID:1617976

Zhao, Long; Kaiser, Ralf I.; Lu, Wenchao; +8 more

A Free-Radical Prompted Barrierless Gas-Phase Synthesis of Pentacene

Journal Article · 2020 · Angewandte Chemie (International Edition) · OSTI ID:1617977

Zhao, Long; Kaiser, Ralf I.; Lu, Wenchao; +8 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
gas-phase chemistry
hydrogen abstraction/vinylacetylene addition (HAVA)
interstellar medium
mass spectrometry
polycyclic aromatic hydrocarbons (PAHs)

Title: A Unified Mechanism on the Formation of Acenes, Helicenes, and Phenacenes in the Gas Phase

Citation Formats

References (39)

Similar Records

Related Subjects