Electron-Deficient Polycyclic Molecules via Ring Fusion for n-Type Organic Electrochemical Transistors

Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202213737. doi: 10.1002/anie.202213737. Epub 2022 Dec 1.

Abstract

The primary challenge for n-type small-molecule organic electrochemical transistors (OECTs) is to improve their electron mobilities and thus the key figure of merit μC*. Nevertheless, few reports in OECTs have specially proposed to address this issue. Herein, we report a 10-ring-fused polycyclic π-system consisting of the core of naphthalene bis-isatin dimer and the terminal moieties of rhodanine, which features intramolecular noncovalent interactions, high π-delocalization and strong electron-deficient characteristics. We find that this extended π-conjugated system using the ring fusion strategy displays improved electron mobilities up to 0.043 cm2 V-1 s-1 compared to our previously reported small molecule gNR, and thereby leads to a remarkable μC* of 10.3 F cm-1 V-1 s-1 in n-type OECTs, which is the highest value reported to date for small-molecule OECTs. This work highlights the importance of π-conjugation extension in polycyclic-fused molecules for enhancing the performance of n-type small-molecule OECTs.

Keywords: Electrochemical Transistors; Ionic-Electronic Conductors; Organic; Ring Fusion; n-Type.