A Modular Approach Toward BN-Embedded Terrylene Diimides

Abstract

This work presents the first example of heteroatoms embedded terrylene diimides (TDIs), which were synthesized from the BN-embedded imide building block in a modular manner. Through the control of the amount and orientations of the BN unit(s), the manipulation of dipole moments of the obtained BN-embedded terrylene diimides (BN-TDIs) was achieved, which in turn extended the fluorescence of BN-TDIs to near infrared region. The structures of BN-TDIs were established via single crystal X-ray diffractions. Stronger carbonyl-π interactions were observed for BN-TDIs in their crystal structures compared with that of TDI, which could be utilized in the construction of supramolecular architectures. The organic thin film transistors based on BN-TDIs were also fabricated. BN-TDI-S showcased higher electron mobilities than that of TDI, indicating the potential of BN-TDIs as promising n-type organic semiconductors.