| ID | 67507 |
| FullText URL | |
| Author |
Oguma, Yukiko
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University
Yamamoto, Masanori
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University
Sunatsuki, Yukinari
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University
Ota, Hiromi
Department of Instrumental Analysis, Advanced Science Research Center, Okayama University
Yamaji, Minoru
Division of Molecular Science, Graduate School of Science and Engineering, Gunma University
Okamoto, Hideki
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University
ORCID
Kaken ID
researchmap
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| Abstract | [32](1,4)Naphthalenophanes, bearing carbon-bridge chains (syn- and anti-NPs) and nitrogen-bridge chains (syn- and anti-ANPs), were synthesized, and their X-ray structures and photoreactions were investigated. The intramolecular separation distance between the naphthalene cores for ANPs was shorter than that for NPs, suggesting that intramolecular interactions between the naphthalene rings were more efficient for ANPs compared to NPs. Upon photoirradiation at 300 nm, anti-NP, syn-ANP and anti-ANP produced the corresponding intramolecular [π4s + π4s] cycloadducts, whereas syn-NP gave an unidentified complex product mixture. Quantum yields for the photo-consumption (ΦPC) of NPs and ANPs were evaluated to quantitatively compare their photoreactivity. The ΦPC values of ANPs were approximately two-fold higher than those of ANPs.Noteworthily, the ΦPC value of syn-ANP was estimated to be unity. Based on these results we discuss the effects of the alignments of the naphthalene cores (anti vs. syn) and the bridging elements (C-bridge vs. N-bridge) on the photoreaction efficiencies of [32](1,4)naphthalenophanes.
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| Keywords | Cyclophane
Azacyclophane
Naphthalenophane
Photocycloaddition
[4 + 4] cycloaddition
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| Note | The version of record of this article, first published in Photochemical & Photobiological Sciences, is available online at Publisher’s website: http://dx.doi.org/10.1007/s43630-024-00610-w
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| Published Date | 2024-07-10
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| Publication Title |
Photochemical & Photobiological Sciences
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| Volume | volume23
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| Issue | issue8
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| Publisher | Springer Science and Business Media LLC
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| Start Page | 1509
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| End Page | 1519
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| ISSN | 1474-905X
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| NCID | AA11791060
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| Content Type |
Journal Article
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| language |
English
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| OAI-PMH Set |
岡山大学
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| Copyright Holders | © The Author(s) 2024
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| File Version | publisher
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| PubMed ID | |
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| Web of Science KeyUT | |
| Related Url | isVersionOf https://doi.org/10.1007/s43630-024-00610-w
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| License | http://creativecommons.org/licenses/by/4.0/
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| Citation | Oguma, Y., Yamamoto, M., Sunatsuki, Y. et al. Intramolecular [π4s + π4s] photocycloaddition of carbon- and nitrogen-bridged [32](1,4)naphthalenophanes. Photochem Photobiol Sci 23, 1509–1519 (2024). https://doi.org/10.1007/s43630-024-00610-w
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| Funder Name |
Okayama University
Japan Society for the Promotion of Science
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| 助成番号 | JP17K05976
20K05648
JP23K04877
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