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

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.