The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Acid−Base Actuation of [c 2]Daisy Chains
Abstract
A versatile synthetic strategy, which was conceived and employed to prepare doubly threaded, bistable [c2]daisy chain compounds, is described. Propargyl and 1-pentenyl groups have been grafted onto the stoppers of [c2]daisy chain molecules obtained using a template-directed synthetic protocol. Such [c2]daisy chain molecules undergo reversible extension and contraction upon treatment with acid and base, respectively. The dialkyne-functionalized [c2]daisy chain (AA) was subjected to an [AA+BB] type polymerization with an appropriate diazide (BB) to afford a linear, mechanically interlocked, main-chain polymer. The macromolecular properties of this polymer were characterized by chronocoulometry, size exclusion chromatography, and static light-scattering analysis. The acid-base switching properties of both the monomers and the polymer have been studied in solution, using (1)H NMR spectroscopy, UV/vis absorption spectroscopy, and cyclic voltammetry. The experimental results demonstrate that the functionalized [c2]daisy chains, along with their polymeric derivatives, undergo quantitative, efficient, and fully reversible switching processes in solution. Kinetics measurements demonstrate that the acid/base-promoted extension/contraction movements of the polymeric [c2]daisy chain are actually faster than those of its monomeric counterpart. These observations open the door to correlated molecular motions and to changes in material properties.
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Cites
Muscular Thin Films for Building Actuators and Powering Devices
Feinberg, A. W., Feigel, A., Shevkoplyas, S. S., Sheehy, S., Whitesides, G. M., & Parker, K. K. (2007) · Science · doi:10.1126/science.1146885 · Cited by 765
Cited by
Stimuli-responsive supramolecular polymeric materials
Yan, X., Wang, F., Zheng, B., & Huang, F. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35091b · Cited by 1,631
Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes
Liu, Z., Nalluri, S. K. M., & Stoddart, J. F. (2017) · Chemical Society Reviews · doi:10.1039/c7cs00185a · Cited by 909
Self-citationSupramolecular polymers constructed by crown ether-based molecular recognition
Zheng, B., Wang, F., Dong, S., & Huang, F. (2012) · Chem. Soc. Rev. · doi:10.1039/c1cs15220c · Cited by 674
Design of Collective Motions from Synthetic Molecular Switches, Rotors, and Motors
Dattler, D., Fuks, G., Heiser, J., Moulin, E., Perrot, A., Yao, X., & Giuseppone, N. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00288 · Cited by 469
Mechanically bonded macromolecules
Fang, L., Olson, M. A., Benítez, D., Tkatchouk, E., Goddard III, W. A., & Stoddart, J. F. (2010) · Chem. Soc. Rev. · doi:10.1039/b917901a · Cited by 450
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Metadata
- Authors
- Fang, L., Hmadeh, M., Wu, J., Olson, M. A., Spruell, J. M., Trabolsi, A., Yang, Y.-W., Elhabiri, M., Albrecht-Gary, A.-M., & Stoddart, J. F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-05-06
- Volume
- 131
- Issue
- 20
- Pages
- 7126-7134
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1996609698
- Cited by
- 206
- References
- 1
- FWCI
- 10.86
- Type
- journal article
- Language
- en
- Open access
- closed
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- Fang, L., Hmadeh, M., Wu, J., Olson, M. A., Spruell, J. M., Trabolsi, A., Yang, Y.-W., Elhabiri, M., Albrecht-Gary, A.-M., & Stoddart, J. F. (2009). Acid−Base Actuation of [c 2]Daisy Chains. Journal of the American Chemical Society. https://doi.org/10.1021/ja900859d
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