Intramolecular [π4s + π4s] photocycloaddition of carbon- and nitrogen-bridged [3₂](1,4)naphthalenophanes.

IF 2.7 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY Photochemical & Photobiological Sciences Pub Date : 2024-07-10 DOI:10.1007/s43630-024-00610-w

Yukiko Oguma, Masanori Yamamoto, Yukinari Sunatsuki, Hiromi Ota, Minoru Yamaji, Hideki Okamoto

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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 (Φ_PC) of NPs and ANPs were evaluated to quantitatively compare their photoreactivity. The Φ_PC values of ANPs were approximately two-fold higher than those of ANPs.Noteworthily, the Φ_PC 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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碳和氮桥式 [32](1,4)萘烷的分子内 [π4s + π4s] 光环加成。

[32]合成了带有碳桥链（同步和反 NPs）和氮桥链（同步和反 ANPs）的(1,4)萘烷，并研究了它们的 X 射线结构和光反应。与 NPs 相比，ANPs 的萘核之间的分子内分离距离更短，这表明 ANPs 与 NPs 相比，萘环之间的分子内相互作用更有效。在 300 纳米波长的光照射下，反 ANP、合成 ANP 和反 ANP 产生了相应的分子内 [π4s + π4s] 环加载产物，而合成 ANP 则产生了不明的复合产物混合物。对 NPs 和 ANPs 的光消耗量子产率（ΦPC）进行了评估，以定量比较它们的光活性。ANPs 的 ΦPC 值大约是 ANPs 的两倍。基于这些结果，我们讨论了萘核的排列（反向与同步）和桥接元素（C 桥与 N 桥）对 [32](1,4)萘烷光反应效率的影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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