Gas-Phase Synthesis of Coronene through Stepwise Directed Ring Annulation

Goettl, Shane J.; Tuli, Lotefa B.; Turner, Andrew M.; Reyes, Yahaira; Howlader, A. Hasan; Wnuk, Stanislaw F.; Hemberger, Patrick; Mebel, Alexander M.; Kaiser, Ralf I.

doi:10.1021/jacs.3c03816

Title: Gas-Phase Synthesis of Coronene through Stepwise Directed Ring Annulation

Journal Article · Wed Jul 05 00:00:00 EDT 2023 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.3c03816· OSTI ID:1989589

Goettl, Shane J. ^[1]; Tuli, Lotefa B. ^[2]; Turner, Andrew M. ^[1]; Reyes, Yahaira ^[2]; Howlader, A. Hasan ^[3];

^[2];

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^[2];

^[1]

University of Hawaii at Ma̅noa, Honolulu, HI (United States)
Florida International University, Miami, FL (United States)
Florida International University, Miami, FL (United States); Johns Hopkins University, Baltimore, MD (United States)
Paul Scherrer Institute (PSI), Villigen (Switzerland)

Molecular beam experiments together with electronic structure calculations provide the first evidence of a complex network of elementary gas-phase reactions culminating in the bottom-up preparation of the 24π aromatic coronene (C₂₄H₁₂) molecule–a representative peri-fused polycyclic aromatic hydrocarbon (PAH) central to the complex chemistry of combustion systems and circumstellar envelopes of carbon stars. The gas-phase synthesis of coronene proceeds via aryl radical-mediated ring annulations through benzo[e]pyrene (C₂₀H₁₂) and benzo[ghi]perylene (C₂₂H₁₂) involving armchair-, zigzag-, and arm-zig-edged aromatic intermediates, highlighting the chemical diversity of molecular mass growth processes to polycyclic aromatic hydrocarbons. Furthermore, the isomer-selective identification of five- to six-ringed aromatics culminating with the detection of coronene is accomplished through photoionization and is based upon photoionization efficiency curves along with photoion mass-selected threshold photoelectron spectra, providing a versatile concept of molecular mass growth processes via aromatic and resonantly stabilized free radical intermediates to two-dimensional carbonaceous nanostructures.

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Research Organization:: University of Hawaii at Ma̅noa, Honolulu, HI (United States); Florida International Univ. (FIU), Miami, FL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

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

OSTI ID:: 1989589

Journal Information:: Journal of the American Chemical Society, Vol. 145, Issue 28; Related Information: https://pubs.acs.org/doi/abs/10.1021/jacs.3c03816; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Aromatic compounds
Carbon
Chemical reactions
Hydrocarbons
Hydrogen

Title: Gas-Phase Synthesis of Coronene through Stepwise Directed Ring Annulation

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