Triazapentadienides, C3F7-C(=NR)-N=C(NHR)-C3F7, result from the reaction of primary amines RNH2 with the fluorinated imine C3F7-CF=N-C4F9. The aniline derivative (R = Ph) is a weak monoprotic acid in dmso. Its conjugate base exhibits an extensive coordination chemistry. It acts as a bidentate ligand toward the molecular fragments Pd(C3H5), Rh(c-C8H12), Ir(c-C8H12), and Rh-(CO)2. The chelates [C3F7-C(NPh)-N-C (NPh)-C3F7]2M, M = Mg, Mn, Fe, Co, Ni, Cu, Zn, and Pd, were prepared. In the crystallographically characterized Co complex, the metal is 3d7, S = 3/2 and tetrahedrally coordinated. Spin densities at carbon in the C6H5 and C3F7 groups were estimated from the 1H and 19F contact shifts. Spin delocalization onto phenyl sp2 carbons is ∼10 times greater than onto the fluorinated sp3 carbons.