The synthesis, characterization and photophysical properties of some new cyclotriphosphazene derivatives bearing Schiff base

Aslan F., Demirpençe Z., Tatsız R., Türkmen H., Öztürk A. İ., ARSLAN M.

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, vol.634, pp.1140-1144, 2008 (SCI-Expanded) identifier identifier


Hex a(2-formylphenoxy)cyclotriphosphazene (o-CHO-C6H4O)(6)N3P3 (2) was obtained from the reaction of hexachlorocyclotriphosphazene (1) with salicylaldehyde in the presence of K2CO3 in THF solvent. A series of Schiff bases containing cyclo-triphosphazenes such as [o-(C6H5N=CH)C6H4O](6)N3P3 (3), [o-(1-C10H7N=CH)C6H4O](6)N3P3 (4), [o-(p-HOC6H4N=CH)C6H4O](6)N3P3 (5), [o-(2,3-Cl2C6H3N=CH)C(6)H4O](6)N3P3 (6), [o-(3,4-Cl2C6H3N=CH)C6H4O](6)N3P3 (7), [o-(3,5-(CH3)(2)C6H3N= CH)C6H4O](6)N3P3 (8), [o-(C6H5CH2N=CH)C6H4O](6)N3P3 (9), [o-(p-CH3OC6H4CH2N=CH)C6H4O](6)N3P3 (10), [o-(n-CH3CH2CH2CH2N=CH)C6H4O](6)N3P3 (11), [o-(t-(CH3)(3)CN=CH)C6H4O](6)N3P3 (12), [o-(n-CH3[CH2](10)CH2N=CH)C6H4O](6)N3P3 (13) were synthesized from the reaction of hexa(2-formylphenoxy)cyclotriphosphazene (2) with aniline, 1-naphthylamine, 2-amino-phenol, 2,3-dichloroaniline, 3,4-dichloroaniline, 3,5-di-tert-butylaniline, benzylamine, p-methoxybenzylamine, n-butylamine, tertbutylamine and 1-dodecylamine, respectively The synthesized compounds were obtained in good yield and high purity. The structures of the compounds were confirmed by means of IR, NMR(H-1, C-13, P-31) and elemental analysis. Photophysical properties of the cyclotriphosphazene derivates were investigated in dichloromethane solvent by UV-Vis. spectrophotometry and spectrofluorometry (emission and excitation). Among the synthesized cyclotriphosphazene derivates, the compounds 2, 4, 5, 11 and 12 exhibit emission between 390 and 550 nm at room temperature.