An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors

Fu Peng Wu; Hio Ieng Un; Yongxi Li; Hailiang Hu; Yi Yuan; Bin Yang; Kai Xiao; Wei Chen; Jie Yu Wang; Zuo Quan Jiang; Jian Pei; Liang Sheng Liao

doi:10.1002/chem.201703415

An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors

Fu Peng Wu, Hio Ieng Un, Yongxi Li, Hailiang Hu, Yi Yuan, Bin Yang, Kai Xiao, Wei Chen, Jie Yu Wang, Zuo Quan Jiang, Jian Pei, Liang Sheng Liao

Functional Hybrid Nanomaterials

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

A new electron-deficient unit with a fused 5-membered heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with a cyclohepta-4,6-diene-1,3-diimde unit. The imide bridge endows dithienylbenzenebisimide (BBI) with a fixed planar configuration and low energy levels for both the highest occupied molecular orbital (HOMO; −6.24 eV) and the lowest unoccupied molecular orbit (LUMO; −2.57 eV). Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm² V⁻¹ s⁻¹, which indicates that the BBI is a promising n-type building block for optoelectronics.

Original language	English
Pages (from-to)	14723-14727
Number of pages	5
Journal	Chemistry - A European Journal
Volume	23
Issue number	59
DOIs	https://doi.org/10.1002/chem.201703415
State	Published - Oct 20 2017

Funding

This work was supported by the National Natural Science Foundation of China (21504062 and 21572152), China Postdoctoral Science Foundation Funded Project (2015M581853). Prof. Zhong’an Li is thanked for helpful discussions. Part of this research was conducted at the Center for Nanophase Materials Sciences, which is a DOE user facility. W.C. gratefully acknowledges financial support from the US Department of Energy, Office of Science, Materials Sciences and Engineering Division. The authors also thank Dr. Joseph Strzalka and Dr. Zhang Jiang for assistance with GIWAXS measurements, and Dr. Jong Keum for helpful discussions. Use of the Advanced Photon Source (APS) at the Argonne National Laboratory was supported by the US Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357.

Keywords

electron-deficiency
fused rings
imides
organic semiconductors
thiophenes

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10.1002/chem.201703415

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abstract = "A new electron-deficient unit with a fused 5-membered heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with a cyclohepta-4,6-diene-1,3-diimde unit. The imide bridge endows dithienylbenzenebisimide (BBI) with a fixed planar configuration and low energy levels for both the highest occupied molecular orbital (HOMO; −6.24 eV) and the lowest unoccupied molecular orbit (LUMO; −2.57 eV). Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm2 V−1 s−1, which indicates that the BBI is a promising n-type building block for optoelectronics.",

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AU - Yang, Bin

AU - Xiao, Kai

AU - Chen, Wei

AU - Wang, Jie Yu

AU - Jiang, Zuo Quan

AU - Pei, Jian

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AB - A new electron-deficient unit with a fused 5-membered heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with a cyclohepta-4,6-diene-1,3-diimde unit. The imide bridge endows dithienylbenzenebisimide (BBI) with a fixed planar configuration and low energy levels for both the highest occupied molecular orbital (HOMO; −6.24 eV) and the lowest unoccupied molecular orbit (LUMO; −2.57 eV). Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm2 V−1 s−1, which indicates that the BBI is a promising n-type building block for optoelectronics.

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An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors

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