A spectroelectrochemical study of the reduction of a Schiff base cryptand

The electrochemical reduction of a bicyclic hexaimino Schiff base cryptand 1 (N[(CH2)2N-CH-meta-C6H4-CH=N(CH2)2]3N) and that of one of its strands 2 ((CH3)2CH-N=CH-meta-C6H4-CH=N-CH(CH3)2) has been studied by visible and near infrared in-situ spectroelectrochemical techniques. These results are in good agreement with those obtained using alkali metals, but in this case the effect of the formation of ion pairs is minimized through the use of tetrabutylammonium cations. It is confirmed that 1- and 1= have the same visible and near IR spectrum. The spectrum of the products of the electrochemical reduction of 2 is similar to those of 1- or 1=.