Isolation of Tetracyano-Naphthalenediimide and its Ambient Stable Planar Radical Anion.

Isolation of Tetracyano-Naphthalenediimide and its Ambient Stable Planar Radical Anion.
Angew Chem Int Ed Engl. 2018 Sep 27;:
Authors: Mukhopadhyay P, Kumar Y, Kumar S, Mandal K
Abstract
Herein we report the first isolation of tetracyano-naphthalenediimide [NDI(CN)4] and its radical anion and structural elucidation through spectroscopic and X-ray diffraction studies. The radical anion showed remarkable ambient stability and could be purified by chromatography, which is unique for planar radical anions. The stability is bestowed by multiple H-bonds with the counter ion and through an array of intramolecular noncovalent interactions. The radical anion revealed one of the strongest NDI pi-pi interactions (3.268 Å). Electrochemical studies of [NDI(CN)4] confirmed its extraordinarily low-lying LUMO (-5.0 eV), rendering it one of the strongest electron-deficient planar pi-system to be isolated. The manifold potential that remained concealed till date, can now unfurl from these open- and closed-shell planar pi-systems.
PMID: 30260056 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - September 27, 2018 Category: Chemistry Authors: Mukhopadhyay P, Kumar Y, Kumar S, Mandal K Tags: Angew Chem Int Ed Engl Source Type: research