An aromatic layered foldamer based on a (cis, cis)-squaramide: chiral induction and absolute structure

Kazusa Kuyama; Fumi Takeda; Ayano Ikeda; Kimiko Tanaka; Kosuke Katagiri; Masatoshi Kawahata; Yusuke Okada; Nagao Kobayashi; Hiroyuki Kagechika; Aya Tanatani

doi:10.1039/D5OB00324E

An aromatic layered foldamer based on a (cis, cis)-squaramide: chiral induction and absolute structure†

Kazusa Kuyama,^a Fumi Takeda,^a Ayano Ikeda,^a Kimiko Tanaka,^a Kosuke Katagiri,

^b Masatoshi Kawahata,

^c Yusuke Okada,^d Nagao Kobayashi,

*^d Hiroyuki Kagechika

^e and Aya Tanatani

*^af

Author affiliations

* Corresponding authors

^a Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan
E-mail: tanatani.aya@ocha.ac.jp

^b Department of Chemistry of Functional Molecules, Faculty of Science and Engineering, Konan University, 8-9-1 Okamoto, Higashinada, Kobe, Hyogo 658-8501, Japan

^c Faculty of Pharmaceutical Science, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan

^d Faculty of Textile Science and Technology, Shinshu University, 3-15-1 Tokida, Ueda, Nagano 386-8567, Japan
E-mail: nagaok@shinshu-u.ac.jp

^e Laboratory for Biomaterials and Bioengineering, Institute of Integrated Research, Institute of Science Tokyo, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

^f Institute for Human Life Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan

Abstract

The meta-linked bissquaramides 8 and 9 were synthesized and spectroscopically characterized. Compound 9, composed of two N,N′-dialkyl-N,N′-diphenylsquaramides 6 sharing a common benzene ring, exhibits CD signals characteristic of right-handed helicity, despite the S-chirality of each unit and its left-handed-helical structure in X-ray crystal analysis. This inversion arises from the interaction of the electric transition moments of the two units.

This article is part of the themed collection: Foldamers

Organic & Biomolecular Chemistry

An aromatic layered foldamer based on a (cis, cis)-squaramide: chiral induction and absolute structure†

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An aromatic layered foldamer based on a (cis, cis)-squaramide: chiral induction and absolute structure

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