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Double‐Stranded Helical Oligomers Covalently Bridged by Rotary Cyclic Boronate Esters
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- Hiroki Iida
- Department of Molecular Design and Engineering Graduate School of Engineering Nagoya University, Chikusa-ku Nagoya 464-8603 Japan
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- Kenji Ohmura
- Department of Molecular Design and Engineering Graduate School of Engineering Nagoya University, Chikusa-ku Nagoya 464-8603 Japan
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- Ryuta Noda
- Department of Molecular Design and Engineering Graduate School of Engineering Nagoya University, Chikusa-ku Nagoya 464-8603 Japan
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- Soichiro Iwahana
- Department of Molecular Design and Engineering Graduate School of Engineering Nagoya University, Chikusa-ku Nagoya 464-8603 Japan
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- Hiroshi Katagiri
- Graduate School of Science and Engineering Yamagata University 4-3-16 Jonan, Yonezawa, Yamagata 992-8510 Japan
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- Naoki Ousaka
- Department of Molecular Design and Engineering Graduate School of Engineering Nagoya University, Chikusa-ku Nagoya 464-8603 Japan
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- Taku Hayashi
- Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Chemistry Graduate School of Science Nagoya University Nagoya 464-8602 Japan
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- Yuh Hijikata
- Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Chemistry Graduate School of Science Nagoya University Nagoya 464-8602 Japan
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- Stephan Irle
- Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Chemistry Graduate School of Science Nagoya University Nagoya 464-8602 Japan
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- Eiji Yashima
- Department of Molecular Design and Engineering Graduate School of Engineering Nagoya University, Chikusa-ku Nagoya 464-8603 Japan
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Description
<jats:title>Abstract</jats:title><jats:p>Novel double helices covalently bridged by cyclic boronate esters were synthesized from complementary dimers with an <jats:italic>m</jats:italic>‐terphenyl backbone joined by a chiral or achiral phenylene linker bearing diethyl boronates and diols, respectively. The X‐ray crystallographic analysis and variable‐temperature NMR and circular dichroism measurements, along with theoretical calculations, revealed that the double helices function as a “molecular rotor” in which the cyclic boronate ester units rotate, yielding two stable rotamers at low temperatures. Moreover, our data indicates that the covalently bonded double helices can undergo a unique helix‐inversion simultaneously with a rotational motion of the boronate esters.</jats:p>
Journal
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- Chemistry – An Asian Journal
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Chemistry – An Asian Journal 12 (8), 927-935, 2017-03-14
Wiley