Syntheses, characterizations, thermal and photophysical properties of cyclophosphazenes containing adamantane units

In this study, phenoxy-adamantane substituted cyclophosphazene compounds (5–8) were synthesized in three steps. Firstly; adamantane derivatives (1 and 2) containing alkyne groups were prepared. Secondly; 2,2,4,4,6,6-hexzakis-(2′-azido-1′-ethoxy)-cyclotriphosphazatriene (3) and 2,2,4,4,6,6,8,8-octakis-(2′-azido-1′-ethoxy)-cyclotetraphosphazatetraene (4) were synthesized from the nucleophilic substitutions of 2-azido-1-ethanol with trimer (N3P3Cl6) and tetramer (N4P4Cl8) in THF respectively. Thirdly; cyclophosphazenes containing adamantane units (5–8) were obtained by the Cu(I) catalyzed click reactions of cyclophosphazenes (3 and 4) with compounds 1 and 2. The structural investigations of newly synthesized compounds 1–8 were evaluated by elemental analysis and FT-IR (ATR), mass spectrometry, 1H, 13C, 1H–13C HSQC (for 6) and 31P NMR (for 3–8) spectroscopies. Compound 1–8 were also reported for the first time. The thermal and photophysical properties of 5–8 were investigated.

Graphical abstractIn this work was shown that synthesis and characterization of cyclophosphazenes containing adamantane derivatives. The thermal stabilities and fluorescence spectral properties of these compounds have been investigated in CH2Cl2 solution.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► New cyclophosphazene compounds containing adamantane derivatives were synthesized. ► All compounds were fully characterized by spectroscopic techniques. ► The thermal and photophysical properties of these compounds were investigated.