Synthesis, Structure, and Properties of Two Planar BN-Benzofluorenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-05 DOI:10.1021/acs.orglett.5c00516

Guan Wang, Qianqian Guo, Yue Xin, Zhang Qi, Shiyu Cao, Dawei Tian, Bolin Zhu

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Abstract

Two planar BN doped benzofluorenes (BN-BkF and BN-BjF) were synthesized separately through palladium-catalyzed intramolecular C–C or C–N coupling reactions. The structures of both BN-BkF and BN-BjF are unambiguously confirmed by X-ray crystallographic analysis. Moreover, the BN unit doping leads to a much lower HOMO level and higher LUMO level as compared to their carbon analogues BkF and BjF. In comparison to BkF and BjF, both BN-BkF and BN-BjF exhibit blue shifts in their ultraviolet–visible (UV–vis) absorption and fluorescence emission spectra. Furthermore, halogenation of BN-BkF and BN-BjF afforded monohalogenated BN-benzofluorenes in good yields. These monohalogenated BN-benzofluorenes can serve as convenient intermediates for palladium-catalyzed coupling reactions to yield a series of functionalized BN-benzofluorene derivatives. The UV–vis absorption and emission spectroscopies in dichloromethane of these BN-benzofluorene derivatives were studied, and the photophysics of these compounds exhibited a high degree of substituent dependency.

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两种平面 BN-苯并芴的合成、结构和性质

通过钯催化的分子内 C-C 或 C-N 偶联反应，分别合成了两种平面掺杂 BN 的苯并芴化合物（BN-BkF 和 BN-BjF）。X 射线晶体分析明确证实了 BN-BkF 和 BN-BjF 的结构。此外，与碳类似物 BkF 和 BjF 相比，掺入 BN 单元会导致更低的 HOMO 水平和更高的 LUMO 水平。与 BkF 和 BjF 相比，BN-BkF 和 BN-BjF 的紫外可见吸收光谱和荧光发射光谱都呈现出蓝移现象。此外，对 BN-BkF 和 BN-BjF 进行卤化还可以得到单卤代 BN-苯并芴，而且收率很高。这些单卤化 BN-苯并呋喃可以作为方便的中间体，用于钯催化的偶联反应，生成一系列功能化 BN-苯并呋喃衍生物。研究了这些 BN-苯并芴衍生物在二氯甲烷中的紫外可见吸收光谱和发射光谱，这些化合物的光物理表现出高度的取代基依赖性。

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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.