Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties
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 (&l...
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| Format: | Article |
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MDPI AG
2018-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/23/12/3337 |
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| author | Otohiro Gotsu Tomomi Shiota Hiroki Fukumoto Tomoko Kawasaki-Takasuka Takashi Yamazaki Tomoko Yajima Tomohiro Agou Toshio Kubota |
| author_facet | Otohiro Gotsu Tomomi Shiota Hiroki Fukumoto Tomoko Kawasaki-Takasuka Takashi Yamazaki Tomoko Yajima Tomohiro Agou Toshio Kubota |
| author_sort | Otohiro Gotsu |
| collection | DOAJ |
| description | 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 (<b>4a</b>) and benzoperylene-type (<b>4b</b>) F-PAHs were synthesized using the Mallory reaction of the 1,4-distyrylbenzene-type π-conjugated molecule (<b>3a</b>), which was prepared by addition-defluorination of available octafluorocyclopentene (OFCP) and aryllithium in three steps. The structure of <b>4a</b> 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. |
| first_indexed | 2024-12-21T22:11:28Z |
| format | Article |
| id | doaj.art-0f2a77733961428f9e493f47460eeff5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T22:11:28Z |
| publishDate | 2018-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0f2a77733961428f9e493f47460eeff52022-12-21T18:48:33ZengMDPI AGMolecules1420-30492018-12-012312333710.3390/molecules23123337molecules23123337Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical PropertiesOtohiro Gotsu0Tomomi Shiota1Hiroki Fukumoto2Tomoko Kawasaki-Takasuka3Takashi Yamazaki4Tomoko Yajima5Tomohiro Agou6Toshio Kubota7Department of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, JapanDepartment of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, JapanDepartment of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, JapanDivision of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184-8588, JapanDivision of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184-8588, JapanDepartment of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, JapanDepartment of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, JapanDepartment of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, JapanIntramolecular 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 (<b>4a</b>) and benzoperylene-type (<b>4b</b>) F-PAHs were synthesized using the Mallory reaction of the 1,4-distyrylbenzene-type π-conjugated molecule (<b>3a</b>), which was prepared by addition-defluorination of available octafluorocyclopentene (OFCP) and aryllithium in three steps. The structure of <b>4a</b> 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.https://www.mdpi.com/1420-3049/23/12/3337polycyclic aromatic hydrocarbonsdibenzoanthracenebenzoperyleneπ-conjugated moleculesMallory reactionaddition-defluorinationoctafluorocyclopentene |
| spellingShingle | Otohiro Gotsu Tomomi Shiota Hiroki Fukumoto Tomoko Kawasaki-Takasuka Takashi Yamazaki Tomoko Yajima Tomohiro Agou Toshio Kubota Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties Molecules polycyclic aromatic hydrocarbons dibenzoanthracene benzoperylene π-conjugated molecules Mallory reaction addition-defluorination octafluorocyclopentene |
| title | Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties |
| title_full | Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties |
| title_fullStr | Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties |
| title_full_unstemmed | Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties |
| title_short | Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties |
| title_sort | fluorine containing dibenzoanthracene and benzoperylene type polycyclic aromatic hydrocarbons synthesis structure and basic chemical properties |
| topic | polycyclic aromatic hydrocarbons dibenzoanthracene benzoperylene π-conjugated molecules Mallory reaction addition-defluorination octafluorocyclopentene |
| url | https://www.mdpi.com/1420-3049/23/12/3337 |
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