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 in | Chemical communications (Cambridge, England) Vol. 60; no. 11; pp. 1404 - 1407 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
England
Royal Society of Chemistry
01.02.2024
Royal Society of Chemistry (RSC) |
Subjects | |
Online Access | Get full text |
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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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 USDOE |
ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/d3cc05371g |