Acid/base controllable molecular switch based on a neutral phenanthroline guest penetrated pseudorotaxane

Masahiro Muraoka; Hiromitsu Irie; Yohji Nakatsuji

doi:10.1039/B926010B

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Acid/base controllable molecular switch based on a neutral phenanthroline guest penetrated pseudorotaxane†

Masahiro Muraoka,*^a Hiromitsu Irie^a and Yohji Nakatsuji*^a

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* Corresponding authors

^a Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, Ohmiya, Asahi-ku, Osaka, Japan
E-mail: muraoka@chem.oit.ac.jp, nakatsuji@chem.oit.ac.jp
Fax: +81-6-6957-2135
Tel: +81-6-6954-4273

Abstract

A ditopic macrocycle with a bisamide and a half dibenzo-crown ether component has been newly synthesized and its complexation behavior toward neutral phenanthroline derivatives is reported. The macrocycle can bind phenanthroline derivatives very strongly by hydrogen bonding and π-electron interaction, yielding pseudorotaxane structures. The inclusion complexes show a pH controllable reversible threading–dethreading molecular switching system.

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Supplementary files

Fig. S1: Partial ¹H NMR spectra of an equimolar mixture (19 mM) of 1 and 2b; Fig. S2: Partial ¹H NMR spectra an equimolar mixture (19 mM) of 1 and 3; Fig. S3–S7: ¹H NMR titration curves for 2a, 2b and 3 with 1; Table S1: Association constants thermodynamic parameters for complexes of macrocycle 1 with 2a, 2b and 3; Fig. S8: ¹H NMR spectra of an equimolar mixture (19 mM) of 1 and protonated phenanthroline ( 2a); Fig. S9: Variable temperature ¹H NMR spectral changes for 2a with 1 PDF (406K)

Article information

DOI: https://doi.org/10.1039/B926010B
Article type: Paper
Submitted: 10 Dec 2009
Accepted: 08 Mar 2010
First published: 18 Mar 2010

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Org. Biomol. Chem., 2010,8, 2408-2413

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Acid/base controllable molecular switch based on a neutral phenanthroline guest penetrated pseudorotaxane

M. Muraoka, H. Irie and Y. Nakatsuji, Org. Biomol. Chem., 2010, 8, 2408 DOI: 10.1039/B926010B

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Organic & Biomolecular Chemistry

Acid/base controllable molecular switch based on a neutral phenanthroline guest penetrated pseudorotaxane†

Abstract

Supplementary files

Article information

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Acid/base controllable molecular switch based on a neutral phenanthroline guest penetrated pseudorotaxane

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