Issue 53, 2015

Multifunctional poly(phosphoester)s with two orthogonal protective groups


A novel cyclic phosphate monomer, 2-(2-(benzyloxy)ethoxy)-1,3,2-dioxaphospholane-2-oxide (BnEEP), was developed to generate poly(phosphoester)s containing protected pendant hydroxyl groups by anionic ring-opening polymerization. The hydroxyl-groups were released by a mild catalytic hydrogenation leaving the polymer backbone intact. In addition, the number of pendant hydroxyl groups was varied by copolymerization of BnEEP with ethyl ethylene phosphate (EEP). Furthermore, copolymers of BnEEP with an acetal protected cyclic phosphate, 2-(2,2-dimethyl-1,3-dioxolan-4-yl-methoxy)-2-oxo-1,3,2-dioxaphospholane (GEP), were prepared in order to establish a selective deprotection of the acetal or the benzyl protective groups by acidic hydrolysis or catalytic hydrogenation respectively. No degradation of the polyester backbone was detected under the reported conditions. The novel monomer allows adjustment of the chemical and physical properties of the poly(phosphoester)s and gives access to various side chain functionalities.

Graphical abstract: Multifunctional poly(phosphoester)s with two orthogonal protective groups

Supplementary files

Article information

Article type
20 Apr 2015
07 May 2015
First published
07 May 2015
This article is Open Access
Creative Commons BY license

RSC Adv., 2015,5, 42881-42888

Author version available

Multifunctional poly(phosphoester)s with two orthogonal protective groups

L. K. Müller, T. Steinbach and F. R. Wurm, RSC Adv., 2015, 5, 42881 DOI: 10.1039/C5RA07167D

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