Molecular Russian dolls

Kang Cai; Mark C. Lipke; Zhichang Liu; Jordan Nelson; Tao Cheng; Yi Shi; Chuyang Cheng; Dengke Shen; Ji Min Han; Suneal Vemuri; Yuanning Feng; Charlotte L. Stern; William A. Goddard; Michael R. Wasielewski; J. Fraser Stoddart

doi:10.1038/s41467-018-07673-1

Molecular Russian dolls

Kang Cai, Mark C. Lipke, Zhichang Liu, Jordan Nelson, Tao Cheng, Yi Shi, Chuyang Cheng, Dengke Shen, Ji Min Han, Suneal Vemuri, Yuanning Feng, Charlotte L. Stern, William A. Goddard, Michael R. Wasielewski, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

66 Scopus citations

Abstract

The host-guest recognition between two macrocycles to form hierarchical non-intertwined ring-in-ring assemblies remains an interesting and challenging target in noncovalent synthesis. Herein, we report the design and characterization of a box-in-box assembly on the basis of host-guest radical-pairing interactions between two rigid diradical dicationic cyclophanes. One striking feature of the box-in-box complex is its ability to host various 1,4-disubstituted benzene derivatives inside as a third component in the cavity of the smaller of the two diradical dicationic cyclophanes to produce hierarchical Russian doll like assemblies. These results highlight the utility of matching the dimensions of two different cyclophanes as an efficient approach for developing new hybrid supramolecular assemblies with radical-paired ring-in-ring complexes and smaller neutral guest molecules.

Original language	English (US)
Article number	5275
Journal	Nature communications
Volume	9
Issue number	1
DOIs	https://doi.org/10.1038/s41467-018-07673-1
State	Published - Dec 1 2018

Funding

This research is part of the Joint Center of Excellence in Integrated Nano-Systems (JCIN) at King Abdulaziz City of Science and Technology (KACST) and Northwestern University (NU). Computational investigations were supported by the U.S. National Science Foundation under grant no. EFRI-1332411 (W.A.G. and T.C.). We would like to thank both KACST and NU for their continued support of this research. Electron paramagnetic resonance studies were supported by the U.S. National Science Foundation under Grant No. CHE-1565925 (M.R.W.).

ASJC Scopus subject areas

General Chemistry
General Biochemistry, Genetics and Molecular Biology
General Physics and Astronomy

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10.1038/s41467-018-07673-1

Cite this

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title = "Molecular Russian dolls",

abstract = "The host-guest recognition between two macrocycles to form hierarchical non-intertwined ring-in-ring assemblies remains an interesting and challenging target in noncovalent synthesis. Herein, we report the design and characterization of a box-in-box assembly on the basis of host-guest radical-pairing interactions between two rigid diradical dicationic cyclophanes. One striking feature of the box-in-box complex is its ability to host various 1,4-disubstituted benzene derivatives inside as a third component in the cavity of the smaller of the two diradical dicationic cyclophanes to produce hierarchical Russian doll like assemblies. These results highlight the utility of matching the dimensions of two different cyclophanes as an efficient approach for developing new hybrid supramolecular assemblies with radical-paired ring-in-ring complexes and smaller neutral guest molecules.",

author = "Kang Cai and Lipke, {Mark C.} and Zhichang Liu and Jordan Nelson and Tao Cheng and Yi Shi and Chuyang Cheng and Dengke Shen and Han, {Ji Min} and Suneal Vemuri and Yuanning Feng and Stern, {Charlotte L.} and Goddard, {William A.} and Wasielewski, {Michael R.} and Stoddart, {J. Fraser}",

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AU - Lipke, Mark C.

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AU - Cheng, Tao

AU - Shi, Yi

AU - Cheng, Chuyang

AU - Shen, Dengke

AU - Han, Ji Min

AU - Vemuri, Suneal

AU - Feng, Yuanning

AU - Stern, Charlotte L.

AU - Goddard, William A.

AU - Wasielewski, Michael R.

AU - Stoddart, J. Fraser

PY - 2018/12/1

Y1 - 2018/12/1

N2 - The host-guest recognition between two macrocycles to form hierarchical non-intertwined ring-in-ring assemblies remains an interesting and challenging target in noncovalent synthesis. Herein, we report the design and characterization of a box-in-box assembly on the basis of host-guest radical-pairing interactions between two rigid diradical dicationic cyclophanes. One striking feature of the box-in-box complex is its ability to host various 1,4-disubstituted benzene derivatives inside as a third component in the cavity of the smaller of the two diradical dicationic cyclophanes to produce hierarchical Russian doll like assemblies. These results highlight the utility of matching the dimensions of two different cyclophanes as an efficient approach for developing new hybrid supramolecular assemblies with radical-paired ring-in-ring complexes and smaller neutral guest molecules.

AB - The host-guest recognition between two macrocycles to form hierarchical non-intertwined ring-in-ring assemblies remains an interesting and challenging target in noncovalent synthesis. Herein, we report the design and characterization of a box-in-box assembly on the basis of host-guest radical-pairing interactions between two rigid diradical dicationic cyclophanes. One striking feature of the box-in-box complex is its ability to host various 1,4-disubstituted benzene derivatives inside as a third component in the cavity of the smaller of the two diradical dicationic cyclophanes to produce hierarchical Russian doll like assemblies. These results highlight the utility of matching the dimensions of two different cyclophanes as an efficient approach for developing new hybrid supramolecular assemblies with radical-paired ring-in-ring complexes and smaller neutral guest molecules.

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Molecular Russian dolls

Abstract

Funding

ASJC Scopus subject areas

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CCDC 1851546: Experimental Crystal Structure Determination

CCDC 1851545: Experimental Crystal Structure Determination

CCDC 1851540: Experimental Crystal Structure Determination

Cite this

Molecular Russian dolls

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1851546: Experimental Crystal Structure Determination

CCDC 1851545: Experimental Crystal Structure Determination

CCDC 1851540: Experimental Crystal Structure Determination

Cite this