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Mechanochemical Tuning of the Binaphthyl Conformation at the Air–Water Interface^†

Dr. Daisuke Ishikawa

World Premier International (WPI) Research Centre for Materials, Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 305-0044, Ibaraki (Japan) http://www.nims.go.jp/super/HP/E_home.htm

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Dr. Taizo Mori,

Dr. Taizo Mori

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Dr. Yusuke Yonamine,

Dr. Yusuke Yonamine

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Dr. Waka Nakanishi,

Corresponding Author

Dr. Waka Nakanishi

[email protected]

Waka Nakanishi, World Premier International (WPI) Research Centre for Materials, Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 305-0044, Ibaraki (Japan) http://www.nims.go.jp/super/HP/E_home.htm

David L. Cheung, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

Katsuhiko Ariga, World Premier International (WPI) Research Centre for Materials, Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 305-0044, Ibaraki (Japan) http://www.nims.go.jp/super/HP/E_home.htm

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Dr. David L. Cheung,

Corresponding Author

Dr. David L. Cheung

[email protected]

Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

Present address: School of Chemistry, National University of Ireland Galway, Galway (Ireland)

David L. Cheung, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

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Dr. Jonathan P. Hill,

Dr. Jonathan P. Hill

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Prof. Katsuhiko Ariga,

Corresponding Author

Prof. Katsuhiko Ariga

[email protected]

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

David L. Cheung, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

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Dr. Daisuke Ishikawa,

Dr. Daisuke Ishikawa

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Dr. Taizo Mori,

Dr. Taizo Mori

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Dr. Yusuke Yonamine,

Dr. Yusuke Yonamine

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Dr. Waka Nakanishi,

Corresponding Author

Dr. Waka Nakanishi

[email protected]

David L. Cheung, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

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Dr. David L. Cheung,

Corresponding Author

Dr. David L. Cheung

[email protected]

Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

Present address: School of Chemistry, National University of Ireland Galway, Galway (Ireland)

David L. Cheung, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

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Dr. Jonathan P. Hill,

Dr. Jonathan P. Hill

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

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Prof. Katsuhiko Ariga,

Corresponding Author

Prof. Katsuhiko Ariga

[email protected]

CREST, JST, Sanbancho, Chiyoda-ku, 102-0075, Tokyo (Japan)

David L. Cheung, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow (UK)

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First published: 12 June 2015

https://doi.org/10.1002/ange.201503363

Citations: 19

^†

This work was partly supported by World Premier International Research Center Initiative (WPI Initiative), MEXT (Japan), the Core Research for Evolutional Science and Technology (CREST) program of Japan Science and Technology Agency (JST) (Japan), and JSPS KAKENHI Grant Number 26104541, 26790003, and 259503. T.M. is grateful for financial support in the form of JSPS Postdoctoral Fellowships for Young Scientists. We also gratefully acknowledge support with MS analysis from the Research and Analytical Center for Giant Molecules (Tohoku University).

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Abstract

Gradual and reversible tuning of the torsion angle of an amphiphilic chiral binaphthyl, from −90° to −80°, was achieved by application of a mechanical force to its molecular monolayer at the air–water interface. This 2D interface was an ideal location for mechanochemistry for molecular tuning and its experimental and theoretical analysis, since this lowered dimension enables high orientation of molecules and large variation in the area. A small mechanical energy (<1 kcal mol⁻¹) was applied to the monolayer, causing a large variation (>50 %) in the area of the monolayer and modification of binaphthyl conformation. Single-molecule simulations revealed that mechanical energy was converted proportionally to torsional energy. Molecular dynamics simulations of the monolayer indicated that the global average torsion angle of a monolayer was gradually shifted.

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Mechanochemical Tuning of the Binaphthyl Conformation at the Air–Water Interface†

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Mechanochemical Tuning of the Binaphthyl Conformation at the Air–Water Interface^†