Synthesis of Pyrene Diimide Isomers with Tunable Excimer Emission

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-21 DOI:10.1021/acs.orglett.4c03523

Katherine Johnston, Alison McCostis, Emma Mikita, Emil Jaffal, Julia A. Schneider

引用次数: 0

Abstract

The optoelectronic properties of pyrene diimides (PyDIs) are of strategic interest given the successful application of similar rylene diimides as n-type organic semiconductors in a variety of organic electronics. We present an improved synthesis for 1,5,6,10-pyrene diimide and the first report of its isomer, 1,8,9,10-pyrene diimide. We demonstrate the effect of imide placement on the core structure, optical properties, and electron affinities. Notably, we have discovered that both isomers exhibit tunable aggregation-induced excimer emission and that 1,8,9,10-PyDI exhibits anti-Kasha emission.

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具有可调准分子发射的芘二亚胺异构体的合成

鉴于类似的二甲苯二酰亚胺作为n型有机半导体在各种有机电子学中的成功应用，吡啶二酰亚胺的光电性能具有战略意义。我们提出了一种改进的1,5,6,10-芘二亚胺的合成方法，并首次报道了它的异构体1,8,9,10-芘二亚胺。我们展示了亚胺放置对核心结构、光学性质和电子亲和力的影响。值得注意的是，我们发现这两种异构体都表现出可调节的聚集诱导的准分子发射，并且1,8,9,10- pydi表现出抗kasha发射。

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.