Suit[4]ane

Wenqi Liu; Charlotte L. Stern; J. Fraser Stoddart

doi:10.1021/jacs.0c03408

Suit[4]ane

Wenqi Liu, Charlotte L. Stern, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Suitanes are two-component mechanically interlocked molecules in which one (torso) of the components, with several protruding limbs, is encompassed by another (suit) all-in-one component. This kind of molecular ship-in-a-bottle architecture remains a challenging one to make. Herein, we report a porphyrin-based suit[4]ane, which is composed of a porphyrin with four protruding ligands (two phenyl groups and two bromine atoms) called the limbs that are encompassed by a tricyclic octacationic cyclophane. The suit[4]ane can be obtained by slippage, a mechanism by which the cyclophane is able to open up two of its entrances in order to take up the porphyrin at high temperature and close them down at low temperature, locking the porphyrin inside its binding cavity. Dynamic 1H NMR spectroscopy reveals that the trapped porphyrin inside the cyclophane rocks back and forth in the suit[4]ane about 1000 times a second.

Original language	English (US)
Pages (from-to)	10273-10278
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	23
DOIs	https://doi.org/10.1021/jacs.0c03408
State	Published - Jun 10 2020

Funding

We thank Northwestern University (NU) for their support of this research. We also thank the personnel in the Integrated Molecular Structure Education and Research Center (IMSERC) at NU for their assistance in the collection of the data. This work made use of the NUFAB facility of Northwestern University’s NUANCE Center, which has received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205), the MRSEC program (NSF DMR-1720139) at the Materials Research Center, the International Institute for Nanotechnology (IIN), the Keck Foundation, and the State of Illinois, through the IIN.

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.0c03408

Cite this

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title = "Suit[4]ane",

abstract = "Suitanes are two-component mechanically interlocked molecules in which one (torso) of the components, with several protruding limbs, is encompassed by another (suit) all-in-one component. This kind of molecular ship-in-a-bottle architecture remains a challenging one to make. Herein, we report a porphyrin-based suit[4]ane, which is composed of a porphyrin with four protruding ligands (two phenyl groups and two bromine atoms) called the limbs that are encompassed by a tricyclic octacationic cyclophane. The suit[4]ane can be obtained by slippage, a mechanism by which the cyclophane is able to open up two of its entrances in order to take up the porphyrin at high temperature and close them down at low temperature, locking the porphyrin inside its binding cavity. Dynamic 1H NMR spectroscopy reveals that the trapped porphyrin inside the cyclophane rocks back and forth in the suit[4]ane about 1000 times a second.",

author = "Wenqi Liu and Stern, {Charlotte L.} and Stoddart, {J. Fraser}",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/jacs.0c03408",

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TY - JOUR

T1 - Suit[4]ane

AU - Liu, Wenqi

AU - Stern, Charlotte L.

AU - Stoddart, J. Fraser

PY - 2020/6/10

Y1 - 2020/6/10

N2 - Suitanes are two-component mechanically interlocked molecules in which one (torso) of the components, with several protruding limbs, is encompassed by another (suit) all-in-one component. This kind of molecular ship-in-a-bottle architecture remains a challenging one to make. Herein, we report a porphyrin-based suit[4]ane, which is composed of a porphyrin with four protruding ligands (two phenyl groups and two bromine atoms) called the limbs that are encompassed by a tricyclic octacationic cyclophane. The suit[4]ane can be obtained by slippage, a mechanism by which the cyclophane is able to open up two of its entrances in order to take up the porphyrin at high temperature and close them down at low temperature, locking the porphyrin inside its binding cavity. Dynamic 1H NMR spectroscopy reveals that the trapped porphyrin inside the cyclophane rocks back and forth in the suit[4]ane about 1000 times a second.

AB - Suitanes are two-component mechanically interlocked molecules in which one (torso) of the components, with several protruding limbs, is encompassed by another (suit) all-in-one component. This kind of molecular ship-in-a-bottle architecture remains a challenging one to make. Herein, we report a porphyrin-based suit[4]ane, which is composed of a porphyrin with four protruding ligands (two phenyl groups and two bromine atoms) called the limbs that are encompassed by a tricyclic octacationic cyclophane. The suit[4]ane can be obtained by slippage, a mechanism by which the cyclophane is able to open up two of its entrances in order to take up the porphyrin at high temperature and close them down at low temperature, locking the porphyrin inside its binding cavity. Dynamic 1H NMR spectroscopy reveals that the trapped porphyrin inside the cyclophane rocks back and forth in the suit[4]ane about 1000 times a second.

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Suit[4]ane

Abstract

Funding

ASJC Scopus subject areas

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CCDC 1993288: Experimental Crystal Structure Determination

Cite this

Suit[4]ane

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1993288: Experimental Crystal Structure Determination

Cite this