Issue 5, 2017

Reversible mechanical protection: building a 3D “suit” around a T-shaped benzimidazole axle

Abstract

The T-shaped benzimidazolium/crown ether recognition motif was used to prepare suit[1]anes. These novel mechanically interlocked molecules (MIMs) were fully characterized by 1H and 13C NMR spectroscopy, single-crystal X-ray diffraction, UV-vis absorption and fluorescence spectroscopy. By conversion to a suit[1]ane, a simple benzimidazole was shown to be protected from deprotonation by strong base. Moreover, it was demonstrated that this unique three-dimensional encapsulation can be made reversible, thus introducing the concept of “reversible mechanical protection”; a protecting methodology that may have potential applications in synthetic organic chemistry and the design of molecular machinery.

Graphical abstract: Reversible mechanical protection: building a 3D “suit” around a T-shaped benzimidazole axle

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Febr. 2017
Accepted
14 Marts 2017
First published
28 Marts 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 3898-3904

Reversible mechanical protection: building a 3D “suit” around a T-shaped benzimidazole axle

K. Zhu, G. Baggi, V. N. Vukotic and S. J. Loeb, Chem. Sci., 2017, 8, 3898 DOI: 10.1039/C7SC00790F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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