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Title: Electrochemically addressable trisradical rotaxanes organized within a metal–organic framework

Abstract

The organization of trisradical rotaxanes within the channels of a Zr6-based metal–organic framework (NU-1000) has been achieved postsynthetically by solvent-assisted ligand incorporation. Robust ZrIV–carboxylate bonds are forged between the Zr clusters of NU-1000 and carboxylic acid groups of rotaxane precursors (semirotaxanes) as part of this building block replacement strategy. Ultraviolet–visible–near-infrared (UV-Vis-NIR), electron paramagnetic resonance (EPR), and 1H nuclear magnetic resonance (NMR) spectroscopies all confirm the capture of redox-active rotaxanes within the mesoscale hexagonal channels of NU-1000. Cyclic voltammetry measurements performed on electroactive thin films of the resulting material indicate that redox-active viologen subunits located on the rotaxane components can be accessed electrochemically in the solid state. In contradistinction to previous methods, this strategy for the incorporation of mechanically interlocked molecules within porous materials circumvents the need for de novo synthesis of a metal–organic framework, making it a particularly convenient approach for the design and creation of solid-state molecular switches and machines. In conclusion, the results presented here provide proof-of-concept for the application of postsynthetic transformations in the integration of dynamic molecular machines with robust porous frameworks.

Authors:
; ; ; ; ; ; ; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Oak Ridge Associated Universities, Inc., Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1235145
Alternate Identifier(s):
OSTI ID: 1348348
Grant/Contract Number:  
AC05-06OR23100; FG87ER13808; W911NF-12-1-0130; FA9550-11-C-0028; DGE-0824162; CHE-1266201
Resource Type:
Published Article
Journal Name:
Proceedings of the National Academy of Sciences of the United States of America
Additional Journal Information:
Journal Name: Proceedings of the National Academy of Sciences of the United States of America Journal Volume: 112 Journal Issue: 36; Journal ID: ISSN 0027-8424
Publisher:
Proceedings of the National Academy of Sciences
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; mechanically interlocked molecules; metal–organic framework; molecular switches; rotaxanes radicals

Citation Formats

McGonigal, Paul R., Deria, Pravas, Hod, Idan, Moghadam, Peyman Z., Avestro, Alyssa-Jennifer, Horwitz, Noah E., Gibbs-Hall, Ian C., Blackburn, Anthea K., Chen, Dongyang, Botros, Youssry Y., Wasielewski, Michael R., Snurr, Randall Q., Hupp, Joseph T., Farha, Omar K., and Stoddart, J. Fraser. Electrochemically addressable trisradical rotaxanes organized within a metal–organic framework. United States: N. p., 2015. Web. doi:10.1073/pnas.1514485112.
McGonigal, Paul R., Deria, Pravas, Hod, Idan, Moghadam, Peyman Z., Avestro, Alyssa-Jennifer, Horwitz, Noah E., Gibbs-Hall, Ian C., Blackburn, Anthea K., Chen, Dongyang, Botros, Youssry Y., Wasielewski, Michael R., Snurr, Randall Q., Hupp, Joseph T., Farha, Omar K., & Stoddart, J. Fraser. Electrochemically addressable trisradical rotaxanes organized within a metal–organic framework. United States. doi:https://doi.org/10.1073/pnas.1514485112
McGonigal, Paul R., Deria, Pravas, Hod, Idan, Moghadam, Peyman Z., Avestro, Alyssa-Jennifer, Horwitz, Noah E., Gibbs-Hall, Ian C., Blackburn, Anthea K., Chen, Dongyang, Botros, Youssry Y., Wasielewski, Michael R., Snurr, Randall Q., Hupp, Joseph T., Farha, Omar K., and Stoddart, J. Fraser. Mon . "Electrochemically addressable trisradical rotaxanes organized within a metal–organic framework". United States. doi:https://doi.org/10.1073/pnas.1514485112.
@article{osti_1235145,
title = {Electrochemically addressable trisradical rotaxanes organized within a metal–organic framework},
author = {McGonigal, Paul R. and Deria, Pravas and Hod, Idan and Moghadam, Peyman Z. and Avestro, Alyssa-Jennifer and Horwitz, Noah E. and Gibbs-Hall, Ian C. and Blackburn, Anthea K. and Chen, Dongyang and Botros, Youssry Y. and Wasielewski, Michael R. and Snurr, Randall Q. and Hupp, Joseph T. and Farha, Omar K. and Stoddart, J. Fraser},
abstractNote = {The organization of trisradical rotaxanes within the channels of a Zr6-based metal–organic framework (NU-1000) has been achieved postsynthetically by solvent-assisted ligand incorporation. Robust ZrIV–carboxylate bonds are forged between the Zr clusters of NU-1000 and carboxylic acid groups of rotaxane precursors (semirotaxanes) as part of this building block replacement strategy. Ultraviolet–visible–near-infrared (UV-Vis-NIR), electron paramagnetic resonance (EPR), and 1H nuclear magnetic resonance (NMR) spectroscopies all confirm the capture of redox-active rotaxanes within the mesoscale hexagonal channels of NU-1000. Cyclic voltammetry measurements performed on electroactive thin films of the resulting material indicate that redox-active viologen subunits located on the rotaxane components can be accessed electrochemically in the solid state. In contradistinction to previous methods, this strategy for the incorporation of mechanically interlocked molecules within porous materials circumvents the need for de novo synthesis of a metal–organic framework, making it a particularly convenient approach for the design and creation of solid-state molecular switches and machines. In conclusion, the results presented here provide proof-of-concept for the application of postsynthetic transformations in the integration of dynamic molecular machines with robust porous frameworks.},
doi = {10.1073/pnas.1514485112},
journal = {Proceedings of the National Academy of Sciences of the United States of America},
number = 36,
volume = 112,
place = {United States},
year = {2015},
month = {8}
}

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DOI: https://doi.org/10.1073/pnas.1514485112

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    • Beilstein Journal of Organic Chemistry, Vol. 14
    • DOI: 10.3762/bjoc.14.190