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Gas-phase preparation of the dibenzo[e,l]pyrene (C24H14) butterfly molecule via a phenyl radical-mediated ring annulation.

Gas-phase preparation of the dibenzo[e,l]pyrene (C24H14) butterfly molecule via a phenyl radical-mediated ring annulation.

Authors :
Goettl, Shane J.
Turner, Andrew M.
Sun, Bing-Jian
Chang, Agnes H. H.
Hemberger, Patrick
Kaiser, Ralf I.
Source :
Chemical Communications; 2/7/2024, Vol. 60 Issue 11, p1404-1407, 4p
Publication Year :
2024

Abstract

A high temperature phenyl-mediated addition–cyclization–dehydrogenation mechanism to form peri-fused polycyclic aromatic hydrocarbon (PAH) derivatives—illustrated through the formation of dibenzo[e,l]pyrene (C<subscript>24</subscript>H<subscript>14</subscript>)—is explored through a gas-phase reaction of the phenyl radical (C<subscript>6</subscript>H<subscript>5</subscript>˙) with triphenylene (C<subscript>18</subscript>H<subscript>12</subscript>) utilizing photoelectron photoion coincidence spectroscopy (PEPICO) combined with electronic structure calculations. Low-lying vibrational modes of dibenzo[e,l]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[e,l]pyrene as a strong target for far-IR astronomical surveys. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
13597345
Volume :
60
Issue :
11
Database :
Complementary Index
Journal :
Chemical Communications
Publication Type :
Academic Journal
Accession number :
175189837
Full Text :
https://doi.org/10.1039/d3cc05371g