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Helicity control of π-conjugated foldamers containing D-glucose-based single enantiomeric units as a chiral source

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Abstract

An optically active bithiophene derivative containing a D-glucose residue and two ethynyl groups ((aR)-7) was synthesized and copolymerized with 2,5-diiodothiophene through Sonogashira–Hagihara cross-coupling. The absorption, circular dichroism, photoluminescence and circularly polarized luminescence properties of the resulting polymer (poly-7) were investigated under various solution conditions. Poly-7 exhibited a clear solvent dependence of the optical and chiroptical properties as a result of the interconversion between random-coil and right-handed helical backbones. We also demonstrated that poly-7 emitted right-handed circularly polarized light upon ultraviolet irradiation in the helically folded state. Based on the contrasting results for a previously reported polymer (poly-A), which contained biphenyl units instead of bithiophene units in the main chain, it can be concluded that seemingly mirror-imaged chiral materials can be prepared using a single enantiomer of glucose without the need for the unnatural L-isomer.

Graphical abstract: Helicity control of π-conjugated foldamers containing d-glucose-based single enantiomeric units as a chiral source

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Publication details

The article was received on 05 Oct 2018, accepted on 30 Oct 2018 and first published on 30 Oct 2018


Article type: Paper
DOI: 10.1039/C8PY01436A
Citation: Polym. Chem., 2018, Advance Article
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    Helicity control of π-conjugated foldamers containing D-glucose-based single enantiomeric units as a chiral source

    T. Ikai, S. Minami, S. Awata, S. Shimizu, T. Yoshida, M. Okubo and K. Shinohara, Polym. Chem., 2018, Advance Article , DOI: 10.1039/C8PY01436A

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