Isoindigo-based aza-BODIPY small molecule for N-type organic field-effect transistors
Liang, Dongxu ; Li, Jianhui ; Cui, Shuaiwei ; Ma, Ji ; Liu, Maning LU
; Miao, Chuanqi
; Vivo, Paola
; Yang, Wenjun
and Zhang, Haichang
(2022)
In Dyes and Pigments
208.
- Abstract
To date, most of the reported conjugated materials are p-type semiconductors, while the advances in n-type or ambipolar conjugated materials greatly fall behind those in p-type counterparts. Well-defined n-type semiconductors should possess suitable electron-deficient groups and relatively low lowest unoccupied molecular orbitals (LUMO) levels that facilitate the electron injection and stabilize the electron transport. Thus, developing novel n-type semiconductor materials with strong electron-deficient property, high electron mobility, and competitive stability is still highly desirable, though challenging. Herein, a new isoindigo-based dimeric aza-boron dipyrromethene (aza-BODIPY) chromophore (IIDG-AB) is designed and synthesized.... (More)
To date, most of the reported conjugated materials are p-type semiconductors, while the advances in n-type or ambipolar conjugated materials greatly fall behind those in p-type counterparts. Well-defined n-type semiconductors should possess suitable electron-deficient groups and relatively low lowest unoccupied molecular orbitals (LUMO) levels that facilitate the electron injection and stabilize the electron transport. Thus, developing novel n-type semiconductor materials with strong electron-deficient property, high electron mobility, and competitive stability is still highly desirable, though challenging. Herein, a new isoindigo-based dimeric aza-boron dipyrromethene (aza-BODIPY) chromophore (IIDG-AB) is designed and synthesized. IIDG-AB contains multiple fluorine and unsaturated nitrogen atoms, which endow it with strong electron-deficient property as well as an ultra-low LUMO level of only −4.24 eV. In addition, IIDG-AB features a large conjugation system and a high degree of coplanarity, which are beneficial for effective intermolecular charge transfer. The UV/visible absorption spectra, X-ray diffraction analysis, and morphological studies via atomic force microscopy imaging indicate that the IIDG-AB thin film presents strong aggregation, good π-π stacking, and long-range order packing, all of which are favorable for the electron transfer between neighboring molecules. Furthermore, IIDG-AB-based organic field-effect transistors exhibit a moderate stable n-type behavior with the highest electron mobility of 1.1 × 10−1 cm2 V−1 s−1. This work provides a simple and effective strategy to synthesize highly functional n-type chromophores via a Schiff base reaction between bislactams and heteroaromatic amines, and also paves the way for future design to fabricate high-performance n-type semiconductor materials for a wide range of applications.
(Less)
- author
- Liang, Dongxu
; Li, Jianhui
; Cui, Shuaiwei
; Ma, Ji
; Liu, Maning
LU
; Miao, Chuanqi
; Vivo, Paola
; Yang, Wenjun
and Zhang, Haichang
- publishing date
- 2022-12
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Dyes and Pigments
- volume
- 208
- article number
- 110743
- publisher
- Elsevier
- external identifiers
-
- scopus:85139059142
- ISSN
- 0143-7208
- DOI
- 10.1016/j.dyepig.2022.110743
- language
- English
- LU publication?
- no
- id
- 8869ecc2-fef2-46ff-aae4-6c14a4ce4305
- date added to LUP
- 2023-08-24 12:10:47
- date last changed
- 2023-08-25 10:00:51
@article{8869ecc2-fef2-46ff-aae4-6c14a4ce4305,
abstract = {{<p>To date, most of the reported conjugated materials are p-type semiconductors, while the advances in n-type or ambipolar conjugated materials greatly fall behind those in p-type counterparts. Well-defined n-type semiconductors should possess suitable electron-deficient groups and relatively low lowest unoccupied molecular orbitals (LUMO) levels that facilitate the electron injection and stabilize the electron transport. Thus, developing novel n-type semiconductor materials with strong electron-deficient property, high electron mobility, and competitive stability is still highly desirable, though challenging. Herein, a new isoindigo-based dimeric aza-boron dipyrromethene (aza-BODIPY) chromophore (IIDG-AB) is designed and synthesized. IIDG-AB contains multiple fluorine and unsaturated nitrogen atoms, which endow it with strong electron-deficient property as well as an ultra-low LUMO level of only −4.24 eV. In addition, IIDG-AB features a large conjugation system and a high degree of coplanarity, which are beneficial for effective intermolecular charge transfer. The UV/visible absorption spectra, X-ray diffraction analysis, and morphological studies via atomic force microscopy imaging indicate that the IIDG-AB thin film presents strong aggregation, good π-π stacking, and long-range order packing, all of which are favorable for the electron transfer between neighboring molecules. Furthermore, IIDG-AB-based organic field-effect transistors exhibit a moderate stable n-type behavior with the highest electron mobility of 1.1 × 10<sup>−1</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>. This work provides a simple and effective strategy to synthesize highly functional n-type chromophores via a Schiff base reaction between bislactams and heteroaromatic amines, and also paves the way for future design to fabricate high-performance n-type semiconductor materials for a wide range of applications.</p>}},
author = {{Liang, Dongxu and Li, Jianhui and Cui, Shuaiwei and Ma, Ji and Liu, Maning and Miao, Chuanqi and Vivo, Paola and Yang, Wenjun and Zhang, Haichang}},
issn = {{0143-7208}},
language = {{eng}},
publisher = {{Elsevier}},
series = {{Dyes and Pigments}},
title = {{Isoindigo-based aza-BODIPY small molecule for N-type organic field-effect transistors}},
url = {{http://dx.doi.org/10.1016/j.dyepig.2022.110743}},
doi = {{10.1016/j.dyepig.2022.110743}},
volume = {{208}},
year = {{2022}},
}