Synthesis of Diketopyrrolopyrrole Based Photoactive Materials via Photoredox C‐H Activation

IF 3 4区 化学 Q3 CHEMISTRY, PHYSICAL
Vinay Kumar, Bommaramoni Yadagiri, Surya Prakash Singh
{"title":"Synthesis of Diketopyrrolopyrrole Based Photoactive Materials via Photoredox C‐H Activation","authors":"Vinay Kumar, Bommaramoni Yadagiri, Surya Prakash Singh","doi":"10.1002/cptc.202400069","DOIUrl":null,"url":null,"abstract":"The synthesis of diketopyrrolopyrrole (DPP) derivatives followed the well‐known conventional cross‐coupling methods such as Suzuki, Stille, Sonogashira, and Negishi cross‐coupling reactions. However, these methods required unfavorable reaction conditions, organometallic precursors, and high temperatures. In addition, the synthesis of conventional cross‐coupling partners including organoboranes, stannane, and acetylenes required drastic reaction conditions and strong bases. In this work, a wide variety of thiophene‐diketopyrrolopyrrole (TDPP)‐based semiconducting materials (36 compounds) were synthesized via Pd‐catalysed photoredox methodology by using N‐hydroxyphthalimide (NHP) based coupling partners, which can be readily prepared from N‐hydroxyphthalimide and carboxylic acid or aldehyde derivatives via single step C‐O bond formation reactions with good yield (80‐90%). This methodology minimizes additional synthetic steps, harsh reaction conditions, and high temperature (100‐150 oC). Optoelectronic studies suggest that the synthesized materials have suitable band gap, HOMO and LUMO levels for variety of optoelectronic applications. To the best of our knowledge, this is the first report on the synthesis of TDPP‐based π‐conjugated materials via the photoredox method.","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":null,"pages":null},"PeriodicalIF":3.0000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemPhotoChem","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/cptc.202400069","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

Abstract

The synthesis of diketopyrrolopyrrole (DPP) derivatives followed the well‐known conventional cross‐coupling methods such as Suzuki, Stille, Sonogashira, and Negishi cross‐coupling reactions. However, these methods required unfavorable reaction conditions, organometallic precursors, and high temperatures. In addition, the synthesis of conventional cross‐coupling partners including organoboranes, stannane, and acetylenes required drastic reaction conditions and strong bases. In this work, a wide variety of thiophene‐diketopyrrolopyrrole (TDPP)‐based semiconducting materials (36 compounds) were synthesized via Pd‐catalysed photoredox methodology by using N‐hydroxyphthalimide (NHP) based coupling partners, which can be readily prepared from N‐hydroxyphthalimide and carboxylic acid or aldehyde derivatives via single step C‐O bond formation reactions with good yield (80‐90%). This methodology minimizes additional synthetic steps, harsh reaction conditions, and high temperature (100‐150 oC). Optoelectronic studies suggest that the synthesized materials have suitable band gap, HOMO and LUMO levels for variety of optoelectronic applications. To the best of our knowledge, this is the first report on the synthesis of TDPP‐based π‐conjugated materials via the photoredox method.
通过光氧化 C-H 活化合成基于二酮吡咯并吡咯的光活性材料
二酮吡咯(DPP)衍生物的合成遵循众所周知的传统交叉偶联方法,如铃木、斯蒂尔、园柄和根岸交叉偶联反应。然而,这些方法需要不利的反应条件、有机金属前体和高温。此外,包括有机硼烷、锡烷和乙炔在内的传统交叉偶联剂的合成需要苛刻的反应条件和强碱。在这项工作中,利用基于 N-羟基邻苯二甲酰亚胺(NHP)的偶联剂,通过钯催化光氧化方法合成了多种基于噻吩-二酮吡咯(TDPP)的半导体材料(36 种化合物),这些偶联剂可以很容易地从 N-羟基邻苯二甲酰亚胺和羧酸或醛衍生物通过单步 C-O 键形成反应制备,且收率高(80-90%)。这种方法最大程度地减少了额外的合成步骤、苛刻的反应条件和高温(100-150 oC)。光电研究表明,合成的材料具有适合各种光电应用的带隙、HOMO 和 LUMO 水平。据我们所知,这是首次报道通过光氧化法合成基于 TDPP 的 π 共轭材料。
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
ChemPhotoChem
ChemPhotoChem Chemistry-Physical and Theoretical Chemistry
CiteScore
5.80
自引率
5.40%
发文量
165
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信