Optoelectronic Tuning of Organoborylazadipyrromethenes via Effective Electronegativity at the Metalloid Center

Organoborylazadipyrromethenes were synthesized from free base and fluoroborylazadipyrromethenes and characterized with regard to their structural and electronic properties. B–N bond lengths, along with photophysical and redox behavior, appear dependent on the effective electronegativity at the boron atom as tuned by its substituents, with stronger electronegativity correlating to a shorter B–N bond length, red-shifted absorbance, enhanced fluorescence lifetime and yield, and positively shifted redox potentials.