New bifunctional redox active ligand based on catechol and 2-iminopyridine, 4-imPy-3,6-CatH2 (1), was synthesized by the condensation of 4-amino-3,6-di-tert-butyl-catechol with 2-pyridinecarboxaldehyde. The oxidation of 1 leads to the corresponding iminopyridine-functionalized o-benzoquinone, 4-imPy-3,6-Q (2). The ligands demonstrate coordination abilities typical for o-quinone as well as 2-iminopyridine ligands, and able to form heterometallic complexes with metal fragments at both functions simultaneously. Potassium, manganese and thallium o-semiquinonato complexes of general type (4-imPy-3,6-SQ)M ((4-imPy-3,6-SQ−)K+ (3), (4-imPy-3,6-SQ)Mn(CO)4 (4), (4-imPy-3,6-SQ)Tl (5)) were generated in solution and investigated by means of X-band EPR spectroscopy. o-Quinone 2 reacts with metallic copper to form mononuclear copper(II) bis-o-benzosemiquinonate (4-imPy-3,6-SQ)2Cu (7), oxidizes triarylstibines with a formation of triarylantimony(V) catecholates (4-imPy-3,6-Cat)SbAr3 (where Ar=Ph (8), p-Tol (9)). Molecular structure of 9 in crystal was determined by single-crystal X-ray analysis. Catechol 1 and o-quinone 2 form neutral complexes with zinc(II) and cadmium(II) iodides: ZnI2·(4-imPy-3,6-CatH2) (10), CdI2·(4-imPy-3,6-CatH2) (11), ZnI2·(4-imPy-3,6-Q) (12) and CdI2·(4-imPy-3,6-Q) (13) where iminopyridine-containing catechol and o-quinone acting as N,N′-coordinated neutral ligands. A formation of heterometallic compounds based on new ligands is shown on the example of interaction of triphenylantimony(V) catecholate 8 with CuCl and CdI2 (complexes CuCl·(4-imPy-3,6-Cat)SbPh3 (14) and CdI2·(4-imPy-3,6-Cat)SbPh3 (15), respectively).