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Issue 19, 2014
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Chiroptical and emissive properties of a calix[4]arene-containing chiral poly(p-phenylene ethynylene) with enantioselective recognition ability

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Abstract

Supramolecular chirality was achieved in solutions and thin films of a calixarene-containing chiral aryleneethynylene copolymer. The observed chiroptical activity, which is primarily allied with the formation of aggregates of high molecular weight polymer chains, is the result of a combination of intrachain and interchain effects. The former arises by the adoption of an induced helix-sense by the polymer main-chain while the latter comes from the exciton coupling of aromatic backbone transitions. The co-existence of bulky bis-calix[4]arene units and chiral side-chains on the polymer skeleton prevents efficient π-stacking of neighbouring chains, keeping the chiral assembly highly emissive. In contrast, for a model polymer lacking calixarene moieties, the chiroptical activity is dominated by strong interchain exciton couplings as a result of more favourable packing of polymer chains, leading to a marked decrease of photoluminescence in the aggregate state. The enantiomeric recognition abilities of both polymers towards (R)- and (S)-α-methylbenzylamine were examined. It was found that a significant enantiodiscrimination is exhibited by the calixarene-based polymer in the aggregate state.

Graphical abstract: Chiroptical and emissive properties of a calix[4]arene-containing chiral poly(p-phenylene ethynylene) with enantioselective recognition ability

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Publication details

The article was received on 24 May 2014, accepted on 16 Jun 2014 and first published on 17 Jun 2014


Article type: Paper
DOI: 10.1039/C4PY00729H
Author version available: Download Author version (PDF)
Citation: Polym. Chem., 2014,5, 5793-5803
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    Chiroptical and emissive properties of a calix[4]arene-containing chiral poly(p-phenylene ethynylene) with enantioselective recognition ability

    J. V. Prata, A. I. Costa, G. Pescitelli and H. D. Pinto, Polym. Chem., 2014, 5, 5793
    DOI: 10.1039/C4PY00729H

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