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A Modular Approach Toward BN‐Embedded Terrylene Diimides

Kexiang Zhao, Yu‐Chun Xu, Jing‐Cai Zeng, Yang‐Kun Qu, Jieyu Wang, Jian Pei

2025Angewandte Chemie International Edition14 citationsDOIOpen Access PDF

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.

Topics & Concepts

ImideHeteroatomSupramolecular chemistryDipoleChemistryOrganic semiconductorPhotochemistryMaterials scienceCrystal structureCrystallographyOrganic chemistryRing (chemistry)Synthesis and Properties of Aromatic CompoundsOrganic and Molecular Conductors ResearchPorphyrin and Phthalocyanine Chemistry