Semiconducting Copolymers with Naphthalene Imide/Amide π‐Conjugated Units: Synthesis, Crystallography, and Systematic Structure‐Property‐Mobility Correlations
Abstract
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 cm2 V−1 s−1) followed by PNBL‐3,8‐T2 and PNBA‐2,6‐T2 (0.11 cm2 V−1 s−1), 0.02 cm2 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), π–π 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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Aug 19, 2022
- Source ID
- 10.1002/ange.202208201
Entities
People
- Antonio Facchetti
- Jianglin Wu
- Shirong Lu
- Tobin J. Marks
- Yao Chen
Organizations
- Air Force Research Laboratory
- Argonne National Laboratory
- Chongqing Institute of Green and Intelligent Technology
- National Institute of Standards and Technology
- National Natural Science Foundation of China
- National Science Foundation
- Northwestern University
- Office of Basic Energy Sciences