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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.

SUBMITTER: Zhu K

PROVIDER: S-EPMC5465563 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Reversible mechanical protection: building a 3D "suit" around a T-shaped benzimidazole axle.

Zhu Kelong K Baggi Giorgio G Vukotic V Nicholas VN Loeb Stephen J SJ

Chemical science 20170328 5

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 <sup>1</sup>H and <sup>13</sup>C 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 encapsulatio ...[more]

PMID: 28626559

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