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

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2007-09, Vol.68 (1), p.123-133
• Main Authors: Refat, Moamen S., Killa, Hamada M.A., Grabchev, Ivo, El-Sayed, Mohamed Y.
• Format: Article
• Language: English
• Subjects: Amides - analysis; Amides - chemical synthesis; Chemistry Techniques, Analytical - methods; CT complexes; Electric Conductivity; Electrons; Indicators and Reagents - chemistry; Kinetics; Light; Magnetic Resonance Spectroscopy - methods; Methanol - chemistry; Models, Chemical; N, N′-Bis[2-hydroxyethyl]-1,4,6,8-naphthalenediimide; Naphthalenes - analysis; Naphthalenes - chemical synthesis; Phenanthrolines - chemistry; Phenol - chemistry; Phenolic acceptors; Spectrophotometry, Infrared - methods; Spectrophotometry, Ultraviolet - methods; Temperature; Thermal studies; Thermodynamics
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2006.10.055

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 1H 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–π * transition. The donor site involved in CT interaction is the diimide two nitrogen atoms by forming hydrogen bonding. The kinetic thermodynamic parameters like Δ E, Δ H, Δ S and Δ G are calculated from the DTG diagrams using Coats–Redfern method. The electrical conductivity properties for the solid CT complexes were measured within the temperature of room 25 °C.