Nucleophilic substitution reactions of phenolphthalein with different substituted cyclotriphosphazene derivatives

In the present work, the partially or fully substituted phenolphthalein bridged cyclotriphosphazene derivatives and their spectral properties were reported for the first time. The reactions of phenolphthalein (2), with racemic trans-2,4-bis(dibenzylamino)-2,4,6,6-tetrachlorocyclotriphosphazene (3), 2,2,4,4-tetra(anilino)-6,6-dichlorocyclotriphosphazene (4), 2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene (5) and 2,2,4,4,6-pentaphenoxy-6-chlorocyclotriphosphazene (6) in THF gave phenolphthalein bridged cyclotriphosphazene compounds 7–10. All these compounds (7–10) were fully characterized by elemental analysis, FT-IR, mass (MS), 1H, 13C and 31P NMR, electronic absorption and fluorescence spectroscopies. The fluorescence properties of novel phenolphthalein bridged dibenzylamino, anilino, thiophenoxy and phenoxy substituted cyclotriphosphazene compounds (7–10) were investigated and compared in dichloromethane.

Graphical abstractIn the present work, the partially or fully substituted phenolphthalein bridged cyclotriphosphazene derivatives and their spectral properties were reported for the first time. The reactions of phenolphthalein (2), with racemic trans-2,4-bis(dibenzylamino)-2,4,6,6-tetrachlorocyclotriphosphazene (3), 2,2,4,4-tetra(anilino)-6,6-dichlorocyclotriphosphazene (4), 2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene (5) and 2,2,4,4,6-pentaphenoxy-6-chlorocyclotriphosphazene (6) in THF gave phenolphthalein bridged cyclotriphosphazene compounds 7–10. All these compounds (7–10) were fully characterized by elemental analysis, FT-IR, mass (MS), 1H, 13C and 31P NMR, electronic absorption and fluorescence spectroscopies. The fluorescence properties of novel phenolphthalein bridged dibenzylamino, anilino, thiophenoxy and phenoxy substituted cyclotriphosphazene compounds (7–10) were investigated and compared in dichloromethane.Figure optionsDownload full-size imageDownload as PowerPoint slide