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Semiconducting Copolymers with Naphthalene Imide/Amide pi-Conjugated Units: Synthesis, Crystallography, and Systematic Structure-Property-Mobility Correlations
Chen, Yao1,2,3; Wu, Jianglin2,3; Lu, Shirong1; Facchetti, Antonio2,3,4; Marks, Tobin J.2,3
2022-08-19
摘要In a series of n-type semiconducting naphthalene tetracarboxydiimide (NDI)-dithiophene (T2) copolymers, structural and electronic properties trends are systematically evaluated as the number of NDI carbonyl groups is reduced from 4 in NDI to 3 in NBL (1-amino-4,5-8-naphthalene-tricarboxylic acid-1,8-lactam-4,5-imide) to 2 in NBA (naphthalene-bis(4,8-diamino-1,5-dicarboxyl)-amide). As the NDI-T2 backbone torsional angle falls the LUMO energy rises. However, the thienyl attachment regiochemistry also plays an important role in less symmetric NBL and NBA. Electron mobility is greatest for N2200 (0.17 cm(2) V-1 s(-1)) followed by PNBL-3,8-T2 and PNBA-2,6-T2 (0.11 cm(2) V-1 s(-1)), 0.02 cm(2) V-1 s(-1) in PNBL-4,8-T2, and negligible in PNBA-3,7-T2. Charge transport reflects a delicate balance between electronic backbone communication (optimum for N2200 and PNBL-4,8-T2), backbone planarity (optimum for PNBA-2,6-T2 and PNBL-3,8-T2), LUMO energy (optimum for N2200), pi-pi stacking distance (optimum for PNBA-2,6-T2), and film crystallinity (optimum for PNBA-2,6-T2 and N2200). These results offer generalizable insight into semiconducting copolymer design.
关键词Charge Transport Crystallinity Naphthalene Imide Amide Organic Electronics Organic Semiconductors
DOI10.1002/anie.202208201
发表期刊ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
页码10
通讯作者Lu, Shirong(lushirong@cigit.ac.cn) ; Facchetti, Antonio(a-facchetti@northwestern.edu) ; Marks, Tobin J.(t-marks@northwestern.edu)
收录类别SCI
WOS记录号WOS:000841804000001
语种英语