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

Shane J. Goettl; Andrew M. Turner; Bing-Jian Sun; Agnes H. H. Chang; Patrick Hemberger; Ralf I. Kaiser

doi:10.1039/D3CC05371G

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

Shane J. Goettl,

^a Andrew M. Turner,^a Bing-Jian Sun,^b Agnes H. H. Chang,*^b Patrick Hemberger

*^c and Ralf I. Kaiser

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Hawai‘i at Mānoa, Honolulu, USA
E-mail: ralfk@hawaii.edu

^b Department of Chemistry, National Dong Hwa University, Shoufeng, Hualien 974, Taiwan
E-mail: hhchang@gms.ndhu.edu.tw

^c Paul Scherrer Institute, Villigen, Switzerland
E-mail: patrick.hemberger@psi.ch

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 (C₂₄H₁₄)—is explored through a gas-phase reaction of the phenyl radical (C₆H₅˙) with triphenylene (C₁₈H₁₂) 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.

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Article information

DOI: https://doi.org/10.1039/D3CC05371G
Article type: Communication
Submitted: 03 Nov 2023
Accepted: 30 Nov 2023
First published: 04 Jan 2024

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Chem. Commun., 2024,60, 1404-1407

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

S. J. Goettl, A. M. Turner, B. Sun, A. H. H. Chang, P. Hemberger and R. I. Kaiser, Chem. Commun., 2024, 60, 1404 DOI: 10.1039/D3CC05371G

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