A BODIPY-Bridged Bisphenoxyl Diradicaloid: Solvent-Dependent Diradical Character and Physical Properties

Abstract

We report a new boron dipyrromethene (BODIPY)-bridged bisphenoxyl diradicaloid (2), which showed closed-shell diamagnetic character in less polar solvents such as dichloromethane but open-shell diradical character with paramagnetic activity in the very polar solvent N,N-dimethylformamide. X-ray crystallographic analysis of 2 revealed an anti-parallel stacked dimer structure via intermolecular dipole–dipole interaction, and the observed solvent-dependent diradical character can be explained by the different dihedral angles between the phenoxyl units and the BODIPY bridge, and structural flexibility of the molecule in different solvents. Compound 2 also exhibited solvent-dependent optical and electrochemical properties.

Keywords

• diradicaloid
• quinone
• BODIPY
• solvatochromism
• conformation flexibility