Synthesis of fully substituted sumanenes at the aromatic periphery through hexabromomethylation

Synthesis of fully substituted sumanenes at the aromatic periphery through hexabromomethylation
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通过六溴甲基化在芳香族外围合成完全取代的苏曼烯

DOI:
10.1002/ajoc.202200585
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发表时间:
2023
期刊:
Asian J. Org. Chem
影响因子:
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通讯作者:
H. Sakurai
H. Sakurai
中科院分区:
--
文献类型:
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作者:
H. Nakazawa;Y. Uetake;Y. Yakiyama;H. Sakurai

文献摘要

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2,3,5,6,8,9-六(溴甲基)sumanene是一种外围芳碳上带有溴甲基的六取代sumanene,通过一步反应成功合成,收率97%。单晶X射线结构分析显示形成了二聚体结构。亲核取代引入了几个取代基。与原始的苏马烯相比,这些紫外可见吸收和发射光谱显示出明显的红移,表明六取代的苏马烯共轭体系的扩展。
2,3,5,6,8,9‐Hexakis(bromomethyl)sumanene, a hexa‐substituted sumanene with bromomethyl groups at the peripheral aromatic carbons, was successfully synthesized in 97% yield with a one‐step reaction. Single‐crystal X‐ray structural analysis showed a formation of a dimer structure. The nucleophilic substitution afforded the introduction of several substituents. These UV‐vis absorption and emission spectra showed clear redshift compared with pristine sumanene, indicating the extension of the conjugation system of hexa‐substituted sumanenes.