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Issue 44, 2010
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The investigation of structural and thermosensitive properties of new phosphazene derivatives bearing glycol and amino acid

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Abstract

In this study, hexachlorocyclotriphosphazene, N3P3Cl6 (cylotriphosphazene), was reacted with hydrophilic and hydrophobic groups to synthesize amphiphilic phosphazene derivatives (4–12). Cylotriphosphazene was reacted triethylene glycol monomethyl ether (TEGME), dipropylene glycol monomethyl ether (DPGME), diethylene glycol monobutyl ether (DEGBE), (1 : 3 mole proportion) in the presence of sodium hydride and using tetrahydrofuran (THF) as solvent at −60 °C. Three isomers (nongeminal cis-2,4,6 (1a–3a); nongeminal trans-2,4,6 (1b–3b); geminal 2,2,4 (1c–3c)) were isolated from the reaction of hexachlorocyclotriphosphazatriene (trimer) (1) with TEGME, DPGME and DEGBE. The substitution reactions of cis-tris isomers (1a–3a) with 4-amino butyric acid, 5-amino valeric acid and 6-amino hexanoic acid were separately done to provide amphiphilic phosphazenes (4–12). All compounds were characterized by using elemental analysis, 31P NMR and mass spectroscopy. Thermosensitive properties of compounds were studied. The compounds (4–12) were soluble in both water and organic media that shows they are amphiphilic molecules. Concentration-dependent LCST (Lower Critical Solution Temperature) behaviours of new compounds (4–12) were measured in water. Compounds 7, 9, 11 and 12 exhibited a reversible and thermosensitive phase transition in aqueous medium, from soluble to insoluble states.

Graphical abstract: The investigation of structural and thermosensitive properties of new phosphazene derivatives bearing glycol and amino acid

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Article information


Submitted
09 Jul 2010
Accepted
01 Sep 2010
First published
11 Oct 2010

Dalton Trans., 2010,39, 10685-10691
Article type
Paper

The investigation of structural and thermosensitive properties of new phosphazene derivatives bearing glycol and amino acid

A. Uslu and Ş. Güvenaltın, Dalton Trans., 2010, 39, 10685
DOI: 10.1039/C0DT00818D

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