Spectroscopic study of the interaction between TCNQ and cryptand 222 in chloroform solution

The interaction between 4, 7, 13, 16, 21, 24-hexaoxa-1,10-diazabicyclo [8.8.8] hexacosane (C222) and 7,7,8,8-teracyanoquinodimethane (TCNQ) has been studied in chloroform at 25 degrees C. The results indicate a two step mechanism. At the first step, two adducts (assign as P1 and P2) are formed through equilibrium reactions. In continue and through nonequilibrium reactions the adducts are converted to a final product (assign as P3). Based on the comparison of the spectra of C222-TCNQ mixture with that of Na-18C6-TCNQ mixture, the C222(+)TCNQ-, C222(+)TCNQ(-)TCNQ(o) and (C222(+))(2)(TCNQ(-))(2) are suggested as the P1, P2, and P3, respectively. IR specra of C222 and TCNQ are compared with the spectrum of solid 1:1 TCNQ-C222 complex and the effect of complexation on absorption bands are discussed.