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Molecular Russian dolls

Cai, Kang and Lipke, Mark C. and Liu, Zhichang and Nelson, Jordan and Cheng, Tao and Shi, Yi and Cheng, Chuyang and Shen, Dengke and Han, Ji-Min and Vemuri, Suneal and Feng, Yuanning and Stern, Charlotte L. and Goddard, William A., III and Wasielewski, Michael R. and Stoddart, J. Fraser (2018) Molecular Russian dolls. Nature Communications, 9 . Art. No. 5275. ISSN 2041-1723. PMCID PMC6288134. http://resolver.caltech.edu/CaltechAUTHORS:20181213-075259162

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1038/s41467-018-07673-1DOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6288134PubMed CentralArticle
ORCID:
AuthorORCID
Cai, Kang0000-0002-8883-0142
Liu, Zhichang0000-0003-3412-512X
Cheng, Tao0000-0003-4830-177X
Cheng, Chuyang0000-0002-3834-0479
Goddard, William A., III0000-0003-0097-5716
Wasielewski, Michael R.0000-0003-2920-5440
Stoddart, J. Fraser0000-0003-3161-3697
Additional Information:© 2018 The Author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. Received 03 July 2018; Accepted 30 October 2018; Published 10 December 2018. 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.). Data availability: All the data generated or analyzed during this study are included in this published article (and its supplementary information files) or available from the authors upon reasonable request. The crystallographic data in this study have been deposited in the Cambridge Structural Database under entry IDs CCDC 1851540–185146. Author Contributions: K.C. conceived and designed the research, carried out most of experiments, analyzed the data and composed the manuscript. M.C.L. involved in the single-crystal growths, UV–Vis–NIR and CV measurements. J.-M.H. helped with the CV measurements. C.L.S. did the crystallographic analysis. M.R.W. and J.N. performed the EPR studies. W.A.G. and T.C. performed DFT calculations. M.C.L. and Z.L. did the first revision of the manuscript. Y.F. and S.V. provided some help with the synthesis. Y.S., D.S., and C.C. involved in the discussions and contributed to the manuscript preparation. J.F.S. directed the research. All authors discussed and commented on the manuscript. The authors declare no competing interests.
Funders:
Funding AgencyGrant Number
NSFEFRI-1332411
NSFCHE-1565925
King Abdulaziz City for Science and Technology (KACST)UNSPECIFIED
Northwestern UniversityUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
WAG1311
PubMed Central ID:PMC6288134
Record Number:CaltechAUTHORS:20181213-075259162
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20181213-075259162
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:91750
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Dec 2018 17:21
Last Modified:04 Jan 2019 20:49

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