N -ferrocenyl isonicotinamide, a redox-active 1D hydrogen-bonded chain structure capable of supporting a mixed-valent redox state

摘要: Abstract N-ferrocenyl isonicotinamide was prepared in 28% isolated yield by the acetylation of aminoferrocence with isonicotinoyl chloride THF and 61% HOBt mediated DCC coupling CH2Cl2 characterized NMR, IR, ESI-MS, UV-vis spectroscopy. The structure Nferrocenyl isonicotinamide, C16H14FeN2O, at 100 K exhibits orthorhombic (Pbca) symmetry. isonicotinamide's amide group is twisted 31.7° respect to py 9.7° relative attached Cp ring, contrast planar observed for isomeric (4- Pyridylaminocarbonyl)ferrocene. Adjacent groups form 1D hydrogen bonded chains through CO NH groups; this H-bonding network oriented along [010] direction. Solid state cyclic voltammetry indicates that bonding capable supporting a class III mixed valent redox state. In contrast, MeCN solutions complex exhibit Fc+/0 potential 420-430 mV vs. Ag/AgCl.