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

An optically active bithiophene derivative containing a d -glucose residue and two ethynyl groups ((a R )- 7 ) was synthesized and copolymerized with 2,5-diiodothiophene through Sonogashira–Hagihara cross-coupling. The absorption, circular dichroism, photoluminescence and circularly polarized lumine...

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Bibliographic Details
Published in:Polymer chemistry 2018-12, Vol.9 (46), p.5504-5510
Main Authors: Ikai, Tomoyuki, Minami, Serena, Awata, Seiya, Shimizu, Sho, Yoshida, Takumu, Okubo, Mitsuhiro, Shinohara, Ken-ichi
Format: Article
Language:English
Subjects:
Addition polymerization
Chemical synthesis
Chiral materials
Circular polarization
Copolymerization
Cross coupling
Dependence
Dichroism
Enantiomers
Glucose
Helicity
Luminescence
Optical activity
Optical properties
Photoluminescence
Polarized light
Polymer chemistry
Polymers
Ultraviolet radiation
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Summary:An optically active bithiophene derivative containing a d -glucose residue and two ethynyl groups ((a R )- 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.
ISSN:1759-9954
1759-9962
DOI:10.1039/C8PY01436A