Impacts of alkyl side chain length on film formation and charge transport in π-extended anthradithiophenes

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-07-24 DOI:10.1016/j.dyepig.2025.113067

Hyo Chan Lee , Jeong-Min Seo , Hyo Chan Hong , Tatsuhiro Kojima , Yunseok Jang , Boseok Kang

{"title":"Impacts of alkyl side chain length on film formation and charge transport in π-extended anthradithiophenes","authors":"Hyo Chan Lee , Jeong-Min Seo , Hyo Chan Hong , Tatsuhiro Kojima , Yunseok Jang , Boseok Kang","doi":"10.1016/j.dyepig.2025.113067","DOIUrl":null,"url":null,"abstract":"<div><div>Thienoacenes, particularly anthradithiophene (ADT), have emerged as promising semiconductor materials for organic field-effect transistors (OFETs). ADT, an isoelectronic analogue of pentacene, features an extended π-system with an anthracene core connected to two thiophene rings. To enhance the solubility and stability of solution-processed ADT thin films, alkyl or alkylphenylethynyl side chain substitutions have been proposed. However, the limited understanding of how these side chain modifications influence the optical and electrical properties of ADT derivatives hinders the rational design of high-performance OFETs. To address this challenge, we synthesized a series of ADT derivatives substituted with alkylphenylethynyl groups (C<sub><em>n</em></sub>-PEADT, <em>n</em> = 4, 6, 8, and 10) and systematically studied the effects of varying side chain lengths on crystal structure, optical properties, and electrical performance. Our findings offer valuable insights into the relationship between side chain modifications and the microstructure and performance of these semiconducting materials, contributing to the advancement of organic electronic devices.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"243 ","pages":"Article 113067"},"PeriodicalIF":4.1000,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720825004371","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

Abstract

Thienoacenes, particularly anthradithiophene (ADT), have emerged as promising semiconductor materials for organic field-effect transistors (OFETs). ADT, an isoelectronic analogue of pentacene, features an extended π-system with an anthracene core connected to two thiophene rings. To enhance the solubility and stability of solution-processed ADT thin films, alkyl or alkylphenylethynyl side chain substitutions have been proposed. However, the limited understanding of how these side chain modifications influence the optical and electrical properties of ADT derivatives hinders the rational design of high-performance OFETs. To address this challenge, we synthesized a series of ADT derivatives substituted with alkylphenylethynyl groups (C_n-PEADT, n = 4, 6, 8, and 10) and systematically studied the effects of varying side chain lengths on crystal structure, optical properties, and electrical performance. Our findings offer valuable insights into the relationship between side chain modifications and the microstructure and performance of these semiconducting materials, contributing to the advancement of organic electronic devices.

Abstract Image

查看原文本刊更多论文

烷基侧链长度对π扩展反噻吩成膜和电荷输运的影响

噻吩，特别是蒽噻吩（ADT），已成为有机场效应晶体管（ofet）的半导体材料。ADT是并五苯的等电子类似物，它具有一个扩展π体系，其中一个蒽核连接两个噻吩环。为了提高溶液处理ADT薄膜的溶解度和稳定性，提出了烷基或烷基苯基乙基侧链取代。然而，对这些侧链修饰如何影响ADT衍生物的光学和电学性质的理解有限，阻碍了高性能ofet的合理设计。为了解决这一挑战，我们合成了一系列以烷基苯基乙基取代的ADT衍生物（Cn-PEADT, n = 4、6、8和10），并系统地研究了不同侧链长度对晶体结构、光学性质和电性能的影响。我们的发现为侧链修饰与这些半导体材料的微观结构和性能之间的关系提供了有价值的见解，有助于有机电子器件的进步。

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

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.