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J Am Chem Soc. 2012 Dec 5;134(48):19795-807. doi: 10.1021/ja3086565. Epub 2012 Nov 27.

Lyotropic chiral nematic liquid crystalline aliphatic conjugated polymers based on disubstituted polyacetylene derivatives that exhibit high dissymmetry factors in circularly polarized luminescence.

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1
Department of Polymer Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.

Abstract

We synthesized disubstituted liquid crystalline polyacetylene (diLCPA) derivatives bearing 4-nonyloxy phenyl groups with lyotropic and thermotropic LC behavior. The poly(diphenylacetylene) main chain structure of the diLCPAs and the chirality induced with either chiral moieties or chiral dopants allow the formation of a highly ordered lyotropic N*-LC phase. Circular dichroism (CD) spectra of the diLCPAs imply that one-handed intrachain helical structures are formed in solution, while interchain helical π-stacking between the polymer main chains are formed in cast film and in the N*-LC state. Absorption dissymmetry factors (g(abs)) in the N*-LC state show values on the order of 10(-1). The N*-LC state facilitates the formation of helically π-stacked structures with a high degree of helical ordering of the diLCPA and is indispensable for the generation of circularly polarized luminescence (CPL) with high emission dissymmetry factors (g(em)) on the order of 10(-1). To the best of our knowledge, this is the highest reported value of CPL achieved for aliphatic, conjugated polymers. As an alternative to the thermotropic N*-LC phase, we have found that the lyotropic N*-LC phase of diLCPA could be promising materials possessing CPL functionality for use in next-generation π-conjugated organic optoelectronic devices, displays, and sensors.

PMID:
23150937
DOI:
10.1021/ja3086565
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