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Monitoring Self-Sorting by Electrospray Ionization Mass Spectrometry: Formation Intermediates and Error-Correction during the Self-Assembly of Multiply Threaded Pseudorotaxanes

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Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany
Cite this: J. Am. Chem. Soc. 2010, 132, 7, 2309–2320
Publication Date (Web):February 2, 2010
https://doi.org/10.1021/ja9101369
Copyright © 2010 American Chemical Society

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    Abstract

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    Three binary pseudorotaxanes, which are based on two different secondary ammonium/crown ether binding motifs, have been studied by 1H NMR and 1H,1H EXSY NMR experiments with respect to their thermodynamic stabilities and their axle exchange kinetics. The stability ranking does not follow the order of axle exchange rates, and the thermodynamically most stable axle−wheel combinations assemble only slowly. On the basis of these binding motifs, a series of self-sorting systems have been studied ranging from simple four-component mixtures through sequence-specific pseudorotaxanes to multiply threaded complexes. Because of the mismatch of kinetic and thermodynamic order, wrongly assembled structures are unavoidable, which require error-correction steps to yield the final thermodynamically controlled self-sorted products. These error-correction steps can easily be monitored by electrospray mass spectrometry, when a mixed-flow microreactor is coupled to the ion source to cover second time scales. Self-assembly intermediates, wrongly assembled structures, and the final thermodynamic products can be simultaneously identified. The determination of preferred assembly pathways as well as the formation of dead-end structures provides a clear picture of a rich kinetic behavior of the self-sorting systems under study.

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    A series of 1H NMR spectra recorded during the formation of 11-2H·2PF6 from 1-H·PF6, 2-H·PF6, and 4; 1H NMR and ESI-MS spectra of 15-2H·2PF6, 18b-H·PF6, 19-H·PF6, 20-2H·2PF6, a 1:2 mixture of 3-2H·2PF6 and 6, and a 1:2:1 mixture of 1-H·PF6, 2-H·PF6, and 4; and 1H−1H COSY spectra of 18b-H·PF6 and 20-2H·2PF6. This material is available free of charge via the Internet at http://pubs.acs.org.

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    75. You-Ming Zhang, Xiao-Peng Chen, Guo-Yan Liang, Kai-Peng Zhong, Qi Lin, Hong Yao, Tai-Bao Wei. A novel water soluble pillar[5]arene and phenazine derivative self-assembled pseudorotaxane sensor for the selective detection of Hg 2+ and Ag + with high selectivity and sensitivity. New Journal of Chemistry 2018, 42 (12) , 10148-10152. https://doi.org/10.1039/C8NJ00508G
    76. Zhihua Zhang, Li Shao, Yujuan Zhou, Jie Yang. Pillar[5]arene‐based endo‐cavity and exo‐wall complexation‐drived hierarchical supramolecular polymerization. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (21) , 3529-3533. https://doi.org/10.1002/pola.28738
    77. Zhihua Zhang, Li Shao, Zhentao Li, Guocan Yu, Jie Yang. A cationic water-soluble pillar[7]arene: Synthesis and its fluorescent host−guest complex in water. Tetrahedron Letters 2017, 58 (28) , 2736-2739. https://doi.org/10.1016/j.tetlet.2017.05.095
    78. Cátia Parente Carvalho, Zoe Domínguez, Cristina Domínguez, Hamdy S. El‐Sheshtawy, José Paulo Da Silva, Jesús F. Arteaga, Uwe Pischel. Five‐Component Self‐Assembly of Cucurbituril‐Based Hetero‐pseudorotaxanes. ChemistryOpen 2017, 6 (2) , 288-294. https://doi.org/10.1002/open.201600173
    79. Pol Besenius. Controlling supramolecular polymerization through multicomponent self‐assembly. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (1) , 34-78. https://doi.org/10.1002/pola.28385
    80. Jürgen H. Gross. Electrospray Ionization. 2017, 721-778. https://doi.org/10.1007/978-3-319-54398-7_12
    81. Bartosz Marzec, Lei Zhang, Nianyong Zhu, Wolfgang Schmitt. Bio-inspired synthetic approaches: from hierarchical, hybrid supramolecular assemblies to CaCO 3 -based microspheres. Dalton Transactions 2017, 46 (19) , 6456-6463. https://doi.org/10.1039/C7DT00914C
    82. Si-Jia Rao, Qi Zhang, Ju Mei, Xu-Hao Ye, Chuan Gao, Qiao-Chun Wang, Da-Hui Qu, He Tian. One-pot synthesis of hetero[6]rotaxane bearing three different kinds of macrocycle through a self-sorting process. Chemical Science 2017, 8 (10) , 6777-6783. https://doi.org/10.1039/C7SC03232C
    83. Zheng Meng, Bo‐Yang Wang, Jun‐Feng Xiang, Qiang Shi, Chuan‐Feng Chen. Self‐Assembly of a [2]Pseudorotaxane by an Inchworm‐Motion Mechanism. Chemistry – A European Journal 2016, 22 (42) , 15075-15084. https://doi.org/10.1002/chem.201602785
    84. Edward A. Neal, Stephen M. Goldup. A Kinetic Self‐Sorting Approach to Heterocircuit [3]Rotaxanes. Angewandte Chemie 2016, 128 (40) , 12676-12681. https://doi.org/10.1002/ange.201606640
    85. Edward A. Neal, Stephen M. Goldup. A Kinetic Self‐Sorting Approach to Heterocircuit [3]Rotaxanes. Angewandte Chemie International Edition 2016, 55 (40) , 12488-12493. https://doi.org/10.1002/anie.201606640
    86. Lucas Powers, David Smithrud. A Versatile Axle for the Construction of Disassemblage Rotaxanes. Molecules 2016, 21 (8) , 1043. https://doi.org/10.3390/molecules21081043
    87. Karol Nowosinski, Stephan Warnke, Kevin Pagel, Dávid Komáromy, Wei Jiang, Christoph A. Schalley. Photooxygenation and gas‐phase reactivity of multiply threaded pseudorotaxanes. Journal of Mass Spectrometry 2016, 51 (4) , 269-281. https://doi.org/10.1002/jms.3746
    88. . Interfaces for Time‐resolved Mass Spectrometry. 2016, 89-156. https://doi.org/10.1002/9781118887332.ch4
    89. Linghui Chen, Zehuan Huang, Jiang-Fei Xu, Zhiqiang Wang, Xi Zhang. Controllable supramolecular polymerization through self-sorting of aliphatic and aromatic motifs. Polymer Chemistry 2016, 7 (7) , 1397-1404. https://doi.org/10.1039/C5PY01923K
    90. Jie Yang, Li Shao, Guocan Yu. Construction of pillar[6]arene-based CO 2 and UV dual-responsive supra-amphiphile and application in controlled self-assembly. Chemical Communications 2016, 52 (15) , 3211-3214. https://doi.org/10.1039/C5CC10617F
    91. Xin Fu, Qi Zhang, Si-Jia Rao, Da-Hui Qu, He Tian. One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy. Chemical Science 2016, 7 (3) , 1696-1701. https://doi.org/10.1039/C5SC04844C
    92. Yiliang Wang, Guchuan Ping, Chunju Li. Efficient complexation between pillar[5]arenes and neutral guests: from host–guest chemistry to functional materials. Chemical Communications 2016, 52 (64) , 9858-9872. https://doi.org/10.1039/C6CC03999E
    93. Bin Hua, Li Shao, Guocan Yu, Feihe Huang. Fluorescence indicator displacement detection based on pillar[5]arene-assisted dye deprotonation. Chemical Communications 2016, 52 (65) , 10016-10019. https://doi.org/10.1039/C6CC04919B
    94. Jie Yang, Li Shao, Jiayin Yuan, Feihe Huang. Construction of a pillar[6]arene based water-soluble supramolecular pseudopolyrotaxane driven by cucurbit[8]uril-enhanced π–π interaction. Chemical Communications 2016, 52 (84) , 12510-12512. https://doi.org/10.1039/C6CC07433B
    95. Guocan Yu, Run Zhao, Dan Wu, Fuwu Zhang, Li Shao, Jiong Zhou, Jie Yang, Guping Tang, Xiaoyuan Chen, Feihe Huang. Pillar[5]arene-based amphiphilic supramolecular brush copolymers: fabrication, controllable self-assembly and application in self-imaging targeted drug delivery. Polymer Chemistry 2016, 7 (40) , 6178-6188. https://doi.org/10.1039/C6PY01402J
    96. Guocan Yu, Jiong Zhou, Jie Shen, Guping Tang, Feihe Huang. Cationic pillar[6]arene/ATP host–guest recognition: selectivity, inhibition of ATP hydrolysis, and application in multidrug resistance treatment. Chemical Science 2016, 7 (7) , 4073-4078. https://doi.org/10.1039/C6SC00531D
    97. Xiaofan Ji, Hu Wang, Yang Li, Danyu Xia, Hao Li, Guping Tang, Jonathan L. Sessler, Feihe Huang. Controlling amphiphilic copolymer self-assembly morphologies based on macrocycle/anion recognition and nucleotide-induced payload release. Chemical Science 2016, 7 (9) , 6006-6014. https://doi.org/10.1039/C6SC01851C
    98. Hua Liu, Wen‐Jing Hu, Yahu A. Liu, Jiu‐Sheng Li, Biao Jiang, Ke Wen. Complexations between Oxacalixcrowns and Secondary Ammonium Salts and ­Construction of an Oxacalixcrown‐Based [2]Rotaxane. European Journal of Organic Chemistry 2015, 2015 (28) , 6270-6277. https://doi.org/10.1002/ejoc.201500893
    99. Hu Wang, Pi Wang, Hao Xing, Ning Li, Xiaofan Ji. A multistimuli‐responsive supramolecular polymer constructed by crown ether‐based molecular recognition and disulfide bond connection. Journal of Polymer Science Part A: Polymer Chemistry 2015, 53 (18) , 2079-2084. https://doi.org/10.1002/pola.27693
    100. Rener Chen, Qizhong Zhou, Bin Zhang, Jiashou Wu, Yuyuan Ye, Guoliang Dai, Huajiang Jiang. K + responsive supramolecular polymer constructed by dibenzo-30-crown-10/paraquat-based molecular recognition. Journal of Polymer Science Part A: Polymer Chemistry 2015, 53 (10) , 1178-1181. https://doi.org/10.1002/pola.27569
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