m-Phenylenediamine-based high-spin dication diradicals: Analysis of the decomposed products

A tetraaryl-m-phenylenediamine dication diradical in the triplet ground state was chemically generated and decomposed in preparative scale. The obtained mixture was separated and purified to examine the decomposed products. A nitro compound and a biaryl were formed as the main products, indicating the cleavage of the pi-conjugation. The relationship between the substituent influence and the structure of the decomposed products, and reaction mechanism are reported. These results serve for establishing guidelines for molecular designing of next-generation charged high-spin molecular systems such as oligoarylamine-based pluri-charged high-spin molecules, in a more sophisticated manner.

A tetraaryl-m-phenylenediamine dication diradical, which exhibits ground-state triplet, was chemically generated and decomposed in preparative scale. A nitro compound and a biaryl were formed as main products, indicating the cleavage of pi-system.Figure optionsDownload as PowerPoint slide