Interaction of N, N `-bis {[}2-N, N-dimethylaminoethyl)]-1,4,6,8-naphthalene-diimide with para substituted phenols: preparation and spectroscopic characterization of charge-transfer complexes and their conductivity measurements with polystyrene composites

Charge-transfer (CT) complexes formed from the reaction of N, N'-bis-{[}2-N,N-dimethylaminoethyl)]1,4,6,8-naphthalenediimide(BDMAENDI) with some phenolic acceptors such as 4-aminophenol (4AP), 4-methylphenol (4MP) and 4-nitrophenol (4NP) have been studied in methanol at 298 K. The final products have been isolated and characterization using UV-Vis., mid-infrared, and H-1-NMR spectra and thermal measurements (TGA and DTG) as well as elemental analysis for CHN. The photometric titration curves for the reactions indicated that the 1: 2 charge transfer complexes {[}(BDMAENDI)(4AP) 2], {[}(BDMAENDI)(4MP) 2] and {[}(BDMAENDI)(4NP) 2] were formed. The infrared and 1H-NMR spectra interpreted that the mode of CT interaction associated with the hydrogen bonding exists between a proton (-OH) of a phenolic acceptor and the (donor) lone pair electron on nitrogen on the two dimethylaminoethyl groups attached to 1,4,6,8-naphthalene-diimide. The activation parameters Delta E, Delta H, Delta S and Delta G were obtained from the DTG diagrams by using the Coats-Redfern method. The polymer composites of {[}(BDMAENDI)(acceptor) 2] charge transfer complex with polystyrene were prepared by weight ratio (1: 5), respectively. The polymer composites exhibit semiconducting behavior with thermal activation energies in the range of 0.36 to 0.70 eV at different temperature.