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Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties

1
Department of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, Japan
2
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184-8588, Japan
3
Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan
*
Authors to whom correspondence should be addressed.
Academic Editor: Pierre-Antoine Bouit
Molecules 2018, 23(12), 3337; https://doi.org/10.3390/molecules23123337
Received: 20 November 2018 / Revised: 10 December 2018 / Accepted: 11 December 2018 / Published: 16 December 2018
Intramolecular photocyclization of stilbene derivatives (Mallory reaction) is one of the efficient methods for building polycyclic aromatic hydrocarbon (PAH) frameworks, and is also expected to be applicable to synthesis of fluorine-containing PAHs (F-PAHs). In this study, dibenzoanthracene-type (4a) and benzoperylene-type (4b) F-PAHs were synthesized using the Mallory reaction of the 1,4-distyrylbenzene-type π-conjugated molecule (3a), which was prepared by addition-defluorination of available octafluorocyclopentene (OFCP) and aryllithium in three steps. The structure of 4a originating from π–π interaction was characterized by X-ray crystallographic analysis. The absorption maxima of UV-Vis spectra and emission maxima of photoluminescence spectra of the PAHs were positioned at a longer wavelength compared to those of the corresponding unsubstituted PAHs, presumably due to the electron-withdrawing nature of perfluorocyclopentene (PFCP) units. The effect of PFCP units in F-PAHs was also studied by time-dependent density functional theory (TD-DFT) calculation. View Full-Text
Keywords: polycyclic aromatic hydrocarbons; dibenzoanthracene; benzoperylene; π-conjugated molecules; Mallory reaction; addition-defluorination; octafluorocyclopentene polycyclic aromatic hydrocarbons; dibenzoanthracene; benzoperylene; π-conjugated molecules; Mallory reaction; addition-defluorination; octafluorocyclopentene
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MDPI and ACS Style

Gotsu, O.; Shiota, T.; Fukumoto, H.; Kawasaki-Takasuka, T.; Yamazaki, T.; Yajima, T.; Agou, T.; Kubota, T. Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties. Molecules 2018, 23, 3337.

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