Spectroscopic and structural characterization of the charge-transfer interaction of N,N′-bis-alkyl derivatives of 1,4,6,8-naphthalenediimide with chloranilic and picric acids

Charge-transfer (CT) complexes formed from the reactions of two N,N′-bis-alkyl derivatives of 1,4,6,8-naphthalenediimide such as N,N′-bis[2-hydroxyethyl)]-1,4,6,8-naphthalenediimide (BHENDI) and N,N′-bis-[2-N,N-dimethylaminoethyl)]-1,4,6,8-naphthalenediimide (BDMAENDI) with chloranilic acid (CLA) and piciric acid (PA) as π-acceptors, have been studied spectrophotometrically in methanol and chloroform, respectively at 25 °C. The photometric titration curves for the reactions indicated that the data obtained refer to 1:1 charge-transfer complexes of [(BHENDI)(CLA)], [(BDMAENDI)(CLA)], [(BHENDI)(PA)] and [(BDMAENDI)(PA)] were formed. Benesi-Hildebrand and its modification methods were applied to the determination of association constant (K), molar extinction coefficient (ɛ). The solid CT complexes have been synthesized and characterization by different spectral methods.