PREPARATION OF FUNCTIONALIZED P-PHENYLENEDIAMINE DERIVATIVES USING ARENE IRON CHEMISTRY

Selective displacement of chloride from cyclopentadienyl(1,4-dichlorob enzene)iron(1+) by a series of cyclic secondary amine nucleophiles is described. This selectivity, in combination with further manipulation of the complexes, allows access to a series of unsymmetrical and/or fu nctionalized tetraalkyl-p-phenylenediamine complexes. A series of deme talated phenylenediamines were shown by CV to have redox potentials di stributed over a range of 320 mV, as a consequence of remote functiona lity. Preliminary fluorescence studies on a series of electron accepto r-substituted phenylenediamines indicated quenching of the phenylenedi amine fluorescence, attributable to rapid electron transfer.