Synthesis and Properties of Cyclic π-Conjugated Molecules and Their Dication and Monoradical Cation

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-06-20 DOI:10.1021/acs.orglett.4c02001

Runjie Xu, and , Yoichiro Kuninobu*,

引用次数: 0

Abstract

We synthesized cyclic π-conjugated molecules by double Friedel–Crafts reaction of amino group-substituted 1,2-bis(2-phenylethynyl)benzene with Meldrum’s acid derivative. The structures of the cyclic π-conjugated molecules were determined by single-crystal X-ray structure analysis. The oxidation of the dimethylamino group-substituted π-conjugated molecule with NOBF₄ gave a closed-shell dication that is stable at >210 °C. The monoradical cation of the di(4-methoxyphenyl)amino group-substituted π-conjugated molecule is stable in dichloromethane solution (half-life of nearly 15 days) and shows near-infrared absorption.

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环π共轭分子及其二阳离子和单阳离子的合成与性质。

我们通过氨基取代的 1,2-双(2-苯乙炔基)苯与 Meldrum 酸衍生物的双 Friedel-Crafts 反应合成了环π-共轭分子。通过单晶 X 射线结构分析确定了环π-共轭分子的结构。用 NOBF4 对二甲基氨基取代的 π 共轭分子进行氧化，得到了在 >210 ℃ 下稳定的闭壳阳离子。二（4-甲氧基苯基）氨基取代的π-共轭分子的单阳离子在二氯甲烷溶液中稳定（半衰期近 15 天），并显示出近红外吸收。

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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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.