Gas-phase preparation of the dibenzo[ e,l ]pyrene (C 24 H 14 ) butterfly molecule via a phenyl radical-mediated ring annulation

A high temperature phenyl-mediated addition-cyclization-dehydrogenation mechanism to form peri-fused polycyclic aromatic hydrocarbon (PAH) derivatives-illustrated through the formation of dibenzo[ ]pyrene (C H )-is explored through a gas-phase reaction of the phenyl radical (C H ˙) with triphenylene...

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Published inChemical communications (Cambridge, England) Vol. 60; no. 11; pp. 1404 - 1407
Main Authors Goettl, Shane J, Turner, Andrew M, Sun, Bing-Jian, Chang, Agnes H H, Hemberger, Patrick, Kaiser, Ralf I
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 01.02.2024
Royal Society of Chemistry (RSC)
Subjects
Carbon stars
Celestial bodies
Chemical reactions
Dehydrogenation
Electronic structure
High temperature environments
Out of plane bending
Photoelectrons
Polycyclic aromatic hydrocarbons
Sky surveys (astronomy)
Stellar envelopes
Vibration mode
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Summary:A high temperature phenyl-mediated addition-cyclization-dehydrogenation mechanism to form peri-fused polycyclic aromatic hydrocarbon (PAH) derivatives-illustrated through the formation of dibenzo[ ]pyrene (C H )-is explored through a gas-phase reaction of the phenyl radical (C H ˙) with triphenylene (C H ) utilizing photoelectron photoion coincidence spectroscopy (PEPICO) combined with electronic structure calculations. Low-lying vibrational modes of dibenzo[ ]pyrene exhibit out-of-plane bending and are easily populated in high temperature environments such as combustion flames and circumstellar envelopes of carbon stars, thus stressing dibenzo[ ]pyrene as a strong target for far-IR astronomical surveys.
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USDOE
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc05371g