Aminobisphosphonate Polymers via RAFT and a Multicomponent Kabachnik-Fields Reaction

Patricia R Bachler; Michael D Schulz; Chelsea A Sparks; Kenneth B Wagener; Brent S Sumerlin

doi:10.1002/marc.201500060

Aminobisphosphonate Polymers via RAFT and a Multicomponent Kabachnik-Fields Reaction

Macromol Rapid Commun. 2015 May;36(9):828-33. doi: 10.1002/marc.201500060. Epub 2015 Mar 24.

Authors

Patricia R Bachler¹, Michael D Schulz, Chelsea A Sparks, Kenneth B Wagener, Brent S Sumerlin

Affiliation

¹ George & Josephine Butler Polymer Research Laboratory, Center for Macromolecular Science & Engineering, Department of Chemistry, University of Florida, Gainesville, Florida, 32611-7200, USA.

PMID: 25808663
DOI: 10.1002/marc.201500060

Abstract

Polyacrylamides containing pendant aminobisphosphonate groups are synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization and a multicomponent postpolymerization functionalization reaction. A Moedritzer-Irani reaction installs the phosphonic acid groups on well-defined, RAFT-generated polymers bearing a pendant amine. An alternate route to the same materials is developed utilizing a three-component Kabachnik-Fields reaction and subsequent dealkylation. Kinetics of the RAFT polymerization of the polymer precursor are studied. Successful functionalization is demonstrated by NMR and FTIR spectroscopy and elemental analysis of the final polymers.

Keywords: Kabachnik-Fields; Moedritzer-Irani; aminobisphosphonate; multicomponent reactions; postpolymerization reactions; reversible addition-fragmentation chain transfer.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amines / chemistry*
Diphosphonates / chemistry*
Kinetics
Polymers / chemical synthesis*
Polymers / chemistry*

Substances

Amines
Diphosphonates
Polymers