Synthesis and evaluation of new isoquinoline diimide derivatives as small molecule acceptors for organic solar cells

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2025-06-01 Epub Date: 2025-03-25 DOI:10.1016/j.tet.2025.134616

Alberto Insuasty , Serena Carrara , Doan Vu , Joel José Montalvo-Acosta , Alejandro Ortíz , Conor Hogan , Christopher R. McNeill , Steven J. Langford

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Abstract

In this work we explore the use of the method of oxidation and heterocyclization of naphthalene diimides (NDIs) to obtain five novel isoquinoline diimide derivatives (IQDI 3–7) as new small molecule acceptors. These derivatives comprise a main core based on triphenylamine (TPA) as electron-donor linked to an isoquinoline diimide moiety as a new electron-acceptor (IQDI 3). The effect on the electronic properties of a further functionalization on TPA achieving A-D-A architectures with additional electron acceptors moieties such as carbonyl group (IQDI 4), 3-methylrhodanine (IQDI 5), 1,3-indandione (IQDI 6) and malononitrile (IQDI 7) was studied. Their electrochemical and optoelectronic properties as well as their performance in photovoltaic devices using J52 as electron-donor polymer were studied being IQDI 6 the compound that showed the best PCE % value.

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新型异喹啉二亚胺衍生物作为有机太阳能电池小分子受体的合成与评价

在这项工作中，我们探索了使用萘二亚胺（NDIs）的氧化和杂环化方法获得五种新的异喹啉二亚胺衍生物（IQDI 3-7）作为新的小分子受体。这些衍生物包括一个以三苯胺（TPA）为电子给体的主核，与异喹啉二亚胺片段作为新的电子受体（IQDI 3）相连。研究了进一步功能化TPA与羰基（IQDI 4）、3-甲基罗丹氨酸（IQDI 5）、1,3-吲哚二酮（IQDI 6）和丙二腈（IQDI 7）等电子受体片段实现a -d -a结构对电子性能的影响。以PCE %值最佳的化合物IQDI 6为研究对象，研究了其电化学和光电性能以及在以J52为电子给体聚合物的光伏器件中的性能。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.