Facile Azabenz-Annulations through UV-induced Photocyclization : A Promising Method for Perylenediimide-Based Organic Semiconductors

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Hua Sun
  • Zifeng Mu
  • Canglei Yang
  • Kai Zhang
  • Xingyu Ji
  • Tianshu Zhang
  • Huanda Ding
  • Shifan Wang
  • Liming Dong
  • Jing Zhang

Detail(s)

Original languageEnglish
Article numbere202101323
Journal / PublicationChemistry - An Asian Journal
Volume17
Issue number3
Online published17 Dec 2021
Publication statusPublished - 1 Feb 2022

Abstract

The derivatization of perylenediimides (PDIs) by bay decoration is essential for the development of PDI-based semiconductors owing to their excellent photoelectric properties. Herein, four bis-azabenz-annulated PDIs (bis-AzaBPDIs) are concisely synthesized in high yields through ultraviolet-induced photocyclization, where the reaction processes including aldimine condensation, cyclization, and oxidative re-aromatization are investigated. The optical characterizations and theoretical simulation reveal that the unique properties of the four bis-AzaBPDIs are comparable to their parent PDI. Organic field effect transistors with compounds 2, 3, or 4 as active layers indicated that all compounds showed unipolar electron transport properties with the mobilities of 1.1×10−3, 5.8×10−4, and 8.5×10−6 cm2 V−1 s−1, respectively. These results suggest the great potential of bis-AzaBPDIs as organic semiconductors. The easy preparation approach reported in this work would renew research interest in developing bis-AzaBPDI-based optoelectronic molecules.

Research Area(s)

  • azabenz-annulations, perylenediimides, photocyclization, semiconductors, ultraviolet-induced

Citation Format(s)

Facile Azabenz-Annulations through UV-induced Photocyclization : A Promising Method for Perylenediimide-Based Organic Semiconductors. / Sun, Hua; Mu, Zifeng; Yang, Canglei; Zhang, Kai; Ji, Xingyu; Zhang, Tianshu; Ding, Huanda; Wang, Shifan; Dong, Liming; Zhang, Jing; Zhang, Qichun.

In: Chemistry - An Asian Journal, Vol. 17, No. 3, e202101323, 01.02.2022.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review