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Synthesis and properties of multiblock amphiphilic cyclophanes with chiral aromatic units

Polymer Journal volume 55, pages 1225–1229 (2023)Cite this article

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Abstract

We designed multiblock amphiphilic cyclophanes (CSS, CRR and CSR) that possess twisted aromatic units with axial chirality. Electronic absorption and emission spectroscopy revealed that these cyclophanes are molecularly dispersed in organic solvents, while they form aggregates in aqueous environments. We also found that under aqueous conditions, the chiral aromatic units within cyclophanes CSS and CRR adopt a more planar conformation compared to their diastereomer CSR, demonstrating the possibility of stereoselective recognition. Furthermore, by comparing the corresponding multiblock amphiphiles that are linear and chiral, we found that the macrocyclic structure might be essential for recognition.

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Acknowledgements

This work was supported by Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Engine” (18H05418 and 18H05419 to KK), Grant-in-Aid for Early-Career Scientists (21K14670 to KS), and Grant-in-Aid for Transformative Research Areas “Molecular Cybernetics” (21H05872 to KS). KS also thanks The Foundation for The Promotion of Ion Engineering and The Office of Research Innovation, Tokyo Institute of Technology for their financial support. We also thank Suzukakedai Materials Analysis Division, Open Facility Center, Tokyo Institute of Technology for ESI-TOF-MS spectrometry, and Open Research Facilities for Life Science and Technology, Tokyo Institute of Technology for NMR and CD spectroscopy.

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  1. Kohei Sato

    Present address: Department of Chemistry, School of Science, Kwansei Gakuin University, 1 Gakuen Uegahara, Sanda-shi, Hyogo, 669-1330, Japan

Authors and Affiliations

  1. School of Life Science and Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa, 226-8501, Japan

    Ryoto Matsuda, Haruki Otake, Kohei Sato & Kazushi Kinbara

  2. Living Systems Materialogy Research Group, International Research Frontiers Initiative, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa, 226-8501, Japan

    Kazushi Kinbara

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  1. Ryoto Matsuda
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Correspondence to Kohei Sato or Kazushi Kinbara.

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Matsuda, R., Otake, H., Sato, K. et al. Synthesis and properties of multiblock amphiphilic cyclophanes with chiral aromatic units. Polym J 55, 1225–1229 (2023). https://doi.org/10.1038/s41428-023-00812-6

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