Synthesis and characterization of N,N `-bis{[}2-hydroxyethyl]-1,4,6,8-naphthalenediimide with para substituted of phenols based on charge-transfer complexes

The interaction of charge-transfer (CT) complexes resulted from the reaction of N,N'-bis{[}2-hydroxyethyl]-1,4,6,8-naphthalenediimide (BHENDI) with some various acceptors like as substituted phenols in para position; 4-aminophenol (4AP), 4-methylphenol (4MP) and 4-nitrophenol (4NP) have been studied in methanol at room temperature. The reaction was studied using electronic (UV-vis), mid infrared, and (1)H NMR spectra and thermal measurements (TGA and DTG) as well as elemental analysis CHN. The chemical analysis data of the resulted CT-complexes, BHENDI-acceptors, reveal that the formation of a 1:2 CT complexes in all cases. The interaction of N,N'-bis{[}2-hydroxyethyl]- 1,4,6,8-naphthalenediimide and phenolic acceptors were investigated spectrophotometrically and found two detected CT bands have n-pi{*} transition. The donor site involved in CT interaction is the diimide two nitrogen atoms by forming hydrogen bonding. The kinetic thermodynamic parameters like Delta E, Delta H, AS and Delta G are calculated from the DTG diagrams using Coats-Redfem method. The electrical conductivity properties for the solid CT complexes were measured within the temperature of room 25 degrees C. (c) 2006 Elsevier B.V. All rights reserved.