α,α′-Diamino-p-quinodimethanes with Three Stable Oxidation States

• DOI: 10.1021/acs.orglett.0c02964
• Publication Date: 2020-10-15T21:59:43Z
• Authors: Alok Mahata; Shubhadeep Chandra; Avijit Maiti; D. Krishna Rao; Cem B. Yildiz; Biprajit Sarkar; Anukul Jana
• Keywords: Three Stable Oxidation States; 01 natural sciences; α,α′-Diamino‑p‑quinodimethanes; 0104 chemical sciences

Herein, we report the rational design, synthesis, and characterization of α,α'-diamino-substituted-p-quinodimethanes, which are a group of partially substituted p-quinodimethanes. These exhibit two reversible one-electron redox steps and electrochromism in the ultraviolet, visible, and near-infrared regions. We were able to isolate the crystalline compounds of all three oxidation states: neutral, radical cation, and dication. The obtained results not only create the bridge between p-quinodimethane and α,α,α',α'-tetrasubstituted-p-quinodimethane, but also demonstrate the straightforward modular approach for the synthesis of π-conjugated open-shell compounds.