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New Synthetic Approaches to N ‐Aryl and π‐Expanded Diketopyrrolopyrroles as New Building Blocks for Organic Optoelectronic Materials
Author(s) -
Jiang Wenlin,
Liu Zitong,
Zhu Danlei,
Zheng Wenyu,
Chen Liangliang,
Zhang Xisha,
Zhang Guanxin,
Yi Yuanping,
Jiang Lang,
Zhang Deqing
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202102131
Subject(s) - aryl , furan , salt (chemistry) , chemistry , thiophene , organic semiconductor , combinatorial chemistry , nanotechnology , materials science , organic chemistry , alkyl
Diketopyrrolopyrrole (DPP) as a building block has been intensively investigated for organic semiconductors and light emitting materials. The synthesis of N ‐aryl DPPs remains challenging. Herein, we firstly report a new easily handled synthetic method toward N ‐aryl DPPs through H‐DPP with diaryliodonium salt in the presence of CuI, which shows broad reaction scope. Sixteen N ‐aryl DPPs, including phenyl, furan and thiophene as flanking aromatic groups, were synthesized with yields up to 78 %. These N ‐aryl DPPs are fluorescent in both solutions and solid states, with quantum yields up to 96 % and 40 %, respectively. Moreover, we show that the reaction between H‐DPP and diaryliodonium salt can lead to π‐expanded DPPs by using Pd(OAc) 2 as catalyst. Nine π‐expanded DPPs were obtained in 27–61 % yields. These π‐expanded DPPs exhibit good semiconducting properties with hole mobility of 0.71 cm 2 V −1 s −1 , demonstrating that they are useful building blocks for high performance organic semiconductors.