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Tunable Heck–Mizoroki Reaction of Dibromonaphthalene Diimide with Aryl Ethylenes: Design, Synthesis, and Characterization of Coplanar NDI-Based Conjugated Molecules
An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors
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.
The FET controller: an electron-deficient building block with a fused 5-membered dithienylbenzenebisimide (BBI) ring was synthesized by replacing a cyclopenta-1,3-diene moiety of indacenodithiophene (IDT) with a cyclohepta-4,6-diene-1,3-diimde unit. The imide bridge endows BBI with a fixed planar configuration and both low HOMO and LUMO energy levels. The polymers based on BBI show good n-type characteristics in OFET devices with the best electron mobility up to 0.34 cm2 V−1 s−1 measured under aerobic, ambient conditions.
