Preparation and Characterization of Chromophor Group Containing Cyclotriphosphazenes: I Imino Chromophor Carrying Some Cyclotriphosphazenes

Abstract

Some new substituted cyclotriphosphazenes were prepared by the reaction of hexachlorocyclotriphophazene and 4-hydroxy or 4′-hydroxy Schiff bases as 4′-hydroxybenzylideneaniline, 4′-hydroxy-4-chlorobenzylideneaniline, 4′-hydroxy-2-chlorobenzylidenaniline, 4′-hydroxyfurfurylidenaniline, 4-hydroxybenzylidene-2′-methylaniline, 4-hydroxybenzylidene-2′,6′-dimethylaniline, 4-hydroxybenzylidene-2′-chloroaniline, 4-hydroxybenzylidene-4′-tert-butylaniline, 4′-hydroxybenzylidene-3,4-15-Crown-5-aniline. The structure of compounds with a general formula [NP(OC<inf>6</inf>H<inf>4</inf>CH=N-Ar)<inf>2</inf>]<inf>3</inf>, or [NP(OC<inf>6</inf>H<inf>4</inf>N=CH-Ar)<inf>2</inf>]<inf>3</inf>, was determined by IR, UV, 1H-NMR and elemental analysis. IR spectra of all compounds showed four characteristic bands located at 1633-1601cm-1, 1242-1150cm-1, 1278-1261cm-1 and 958-943cm-1, respectively, corresponding to CH=N, P=N, P-N-P (asymmetric) and P-N-P (symmetric) vibrations. Charasterictic UV bands, named as Band I, Band II, Band III and Band IV located at 346-308nm, 294-271nm, 262-216nm and 240-210nm respectively, are due to electronic transitions. The 1H-NMR spectra of 4-hydroxyfurfurylidene and the phosphazene derivative shows cis-trans izomerization below 305°K and 295°K.