A facile access to N-heteroaryl-fused bis-BODIPY scaffolds has been developed. A BODIPY dimer with an α,α-amine linker serves as a starting material to obtain pyrrole- and pyridine-fused BODIPYs, either by direct oxidation or by oxidative condensation with an aldehyde building block. Both species mark antipodal conjugative coupling conditions that result in distinct spectral outcomes. In stark contrast to the pyrrole fusion, pyridine-coupled species show unique panchromatic absorption profiles.