Self‐Assembling Aryl‐Naphthalendiimide Derivatives with a Nitroxide Radical

Abstract

A series of aryl‐substituted naphthalenediimide derivatives that contain nitroxide radicals were prepared and their crystal structures were elucidated. Much stronger charge‐transfer interactions were present in the derivatives with perfluorobenzene substituents than those with phenyl or 4‐fluorophenyl substituents. These interactions result in the formation of single‐component charge‐transfer complexes by self‐assembly of the naphthalenediimide derivatives to provide black crystals. As a consequence, the naphthalenediimide derivatives with perfluorobenzene substituents have better field‐effect transistor (FET) properties than the other derivatives.

Low Molecular Weight Gelators Bearing Electroactive Groups as Cathode Materials for Rechargeable Batteries

“…Nitroxides, as stable organic radicals, represent an interesting class of molecules that form the basis of novel and emerging functional materials such as radical batteries, spin probes, polarizing agents for DNP–NMR, antioxidants, magneto‐active materials, and radiation protective agents owing to their single component charge‐transfer properties . TEMPO is a persistent radical, which has been protected by four α‐methyl groups.…”

Structures of the reaction products of the AZADO radical with TCNQF4 or thiourea

“…Previously, we observed that the TEMPO radical ( 1 ) forms corresponding charge transfer (CT) complexes with appropriate acceptors such as TCNQF 4 ( 3 ) [6], and even more impressively some TEMPO derivatives with appropriate acceptor units such as 1,4-benzoquinone [7] or naphthalenediimide [8] can form single-component CT complexes by self-assembly. Based on previous results, we next intended to see if similar CT complexes would be formed from AZADO ( 2 ) with an appropriate acceptor.…”