Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-08-12 DOI:10.3762/bjoc.20.172

Siham Asyiqin Shafie, Ryo Nozawa, Hideaki Takano, Hiroshi Shinokubo

引用次数: 0

Abstract

Norcorrole is a stable 16π-antiaromatic porphyrinoid that exhibits characteristic reactivities and physical properties. Here, we disclose the reaction of Ni(II) norcorroles with alkyl radicals derived from azo radical initiators. The radical selectively attacked the distal α-position relative to the meso-position to construct a nonaromatic bowl-shaped structure. The photophysical and electrochemical properties of the obtained radical adducts were compared to those of the parent Ni(II) norcorrole. The radical reactivity of Ni(II) norcorroles was investigated by density functional theory (DFT) calculations.

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Beilstein J. Org. Chem. 2024, 20, 1967–1972. doi:10.3762/bjoc.20.172

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反芳香族 Ni(II) norcorroles 与偶氮自由基引发剂的自由基反应性

摘要Norcorrole 是一种稳定的 16π-反芳香族卟啉，具有独特的反应活性和物理性质。在此，我们揭示了 Ni(II) Norcorroles 与偶氮自由基引发剂衍生的烷基自由基的反应。相对于中间位，自由基选择性地攻击远端 α- 位，从而构建出一种非芳香族的碗状结构。将所获得的自由基加合物的光物理和电化学性质与母体 Ni(II) norcorrole 的光物理和电化学性质进行了比较。通过密度泛函理论（DFT）计算研究了 Ni(II) norcorroles 的自由基反应性。Chem.2024, 20, 1967–1972. doi:10.3762/bjoc.20.172

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

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