具有超深最低未占据分子轨道的萘[2,1-b]-融合AzaBODIPYs的合成、光物理和氧化还原性质

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-31 DOI:10.1021/acs.orglett.5c0141110.1021/acs.orglett.5c01411

Wanle Sheng, Zhangcui Wang, Guoao Wu, Luying Guo, Xing Guo, Erhong Hao* and Lijuan Jiao*,

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引用次数: 0

摘要

通过经典的Michael加成-环化序列，建立了一种简化的免色谱合成构象受限的六元环偶氮杂波dipys的方法。随后，2,3-二氯-5,6-二氰-1,4-苯醌介导的脱氢芳化反应产生了第一个萘[2,1-b]-融合的azaBODIPYs，在氧化后显示出逐渐降低的最低未占据分子轨道（LUMO）水平（高达- 4.39 eV），这与增强的电子接受行为一致。这些新型融合azaBODIPYs具有强烈的近红外吸收，并在钴二茂物存在下形成自由基阴离子，在877 nm处表现出红移吸收最大值。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis, Photophysical, and Redox Properties of Naphtho[2,1-b]-Fused AzaBODIPYs with Ultradeep Lowest Unoccupied Molecular Orbital Levels

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Synthesis, Photophysical, and Redox Properties of Naphtho[2,1-b]-Fused AzaBODIPYs with Ultradeep Lowest Unoccupied Molecular Orbital Levels

A streamlined chromatography-free synthesis of conformationally restricted six-membered-ring-fused azaBODIPYs via a classical Michael addition–cyclization sequence has been developed. Subsequent stepwise 2,3-dichloro-5,6-dicyano-1,4-benzoquinone-mediated dehydrogenative aromatization yields the first naphtho[2,1-b]-fused azaBODIPYs, demonstrating progressively lowered lowest unoccupied molecular orbital (LUMO) levels (up to −4.39 eV) upon oxidation, which aligns with enhanced electron-accepting behavior. These novel fused azaBODIPYs show intense near-infrared absorption and form radical anions in the presence of cobaltocene, exhibiting a red-shifted absorption maxima at 877 nm.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.