Citation: Abdol-reza Hajipour a, b, Sakineh Habibi b, Arnold E. Ruoho a. SYNTHESIS AND CHARACTERIZATION OF NOVEL OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S AND POLY(ESTER-IMIDE)S CONTAINING CALIX[4]ARENE AND AMINO ACID UNITS WITH BINDING ABILITY TOWARDS ALKALI METAL AND TOXIC HEAVY METAL CATIONS[J]. Chinese Journal of Polymer Science, ;2010, 28(5): 731-743. doi: 10.1007/s10118-010-9125-7 shu

SYNTHESIS AND CHARACTERIZATION OF NOVEL OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S AND POLY(ESTER-IMIDE)S CONTAINING CALIX[4]ARENE AND AMINO ACID UNITS WITH BINDING ABILITY TOWARDS ALKALI METAL AND TOXIC HEAVY METAL CATIONS

Received Date: 24 August 2009
Revised Date: 18 November 2009

A novel calix[4]arene derivative 2 with amino functional groups at the lower rim was first prepared via introduction of nitro functional groups and amination of the dinitro derivative of calix[4]arene. The optically active monomers were synthesized by dehydration of L-leucine (and L-isoleucine) and 3,3',4,4'-benzophenonetetracarboxylic-3,3',4,4'-dianhydride (3) followed by reaction with thionyl chloride to form 5a and 5b. Two methods, polymerization under microwave irradiation and solution polymerization in CH2Cl2/TEA, were then employed to carry out the condensation polymerization of 2 with the optically active monomers 5a and 5b, respectively. The polymerization conditions affected the kind of resulting polymers, poly(amide-imide)s (PAIs) 6a and 6b and poly(ester-imide)s (PEIs) 6a' and 6b' were obtained selectively in good yields and moderate inherent viscosities. Sorption-extraction experiments were carried out using cram picrate extraction method and verified good binding ability of the resulting calixarene-based polymers towards silver, alkali metal and toxic heavy metal cations. Also thermogravimetric analysis indicated that the resulting PAIs and PEIs were thermally stable.
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