Embedding a Planar Antiaromatic Cyclooctatetraene into a Truxene-Derived Polycyclic Aromatic Hydrocarbon.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-15 DOI:10.1021/acs.orglett.5c02272

Simone F Ebel,Frank Rominger,Michael Mastalerz

引用次数: 0

Abstract

Two contorted, monkey saddle-shaped polycyclic aromatic hydrocarbons (PAHs) with tailored substitution patterns were synthesized to enhance their inversion barriers. Along the way, a chiral, truxene-based PAH featuring a planar cyclooctatetraene (COT) core was discovered and structurally confirmed by X-ray crystallography. Its antiaromatic character and optoelectronic properties were investigated and compared to those of its negatively curved precursor. Deuterium-labeling experiments and DFT calculations provided insights into the formation of the planar COT ring.

查看原文本刊更多论文

平面反芳环四烯嵌入truxene衍生的多环芳烃。

合成了两种扭曲的猴鞍形多环芳烃（PAHs），它们具有定制的取代模式，以提高它们的反转势垒。在此过程中，发现了一种具有平面环四烯（COT）核心的手性truxene基PAH，并通过x射线晶体学进行了结构证实。研究了其反芳特性和光电性能，并与其负弯曲前驱体进行了比较。氘标记实验和DFT计算提供了对平面COT环形成的见解。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.