Collect. Czech. Chem. Commun.
2003, 68, 1488-1514
https://doi.org/10.1135/cccc20031488
Redox-Induced Ring Shuttling and Evidence for Folded Structures in Long and Flexible Two-Station Rotaxanes
Tohru Yamamotoa, Hsian-Rong Tsenga, J. Fraser Stoddarta,*, Vincenzo Balzanib, Alberto Credib, Filippo Marchionib and Margherita Venturib,*
a Department of Chemistry and Biochemistry, University of California, Los Angeles 405 Hilgard Avenue, Los Angeles, CA 90095-1569, U.S.A.
b Dipartimento di Chimica "G. Ciamician", Università di Bologna, Via Selmi 2, 40126 Bologna, Italy
Crossref Cited-by Linking
- Bazargan Gloria, Sohlberg Karl: Advances in modelling switchable mechanically interlocked molecular architectures. International Reviews in Physical Chemistry 2018, 37, 1. <https://doi.org/10.1080/0144235X.2018.1419042>
- Franchi Paola, Bleve Valentina, Mezzina Elisabetta, Schäfer Christian, Ragazzon Giulio, Albertini Marco, Carbonera Donatella, Credi Alberto, Di Valentin Marilena, Lucarini Marco: Structural Changes of a Doubly Spin‐Labeled Chemically Driven Molecular Shuttle Probed by PELDOR Spectroscopy. Chemistry A European J 2016, 22, 8745. <https://doi.org/10.1002/chem.201601407>
- Lestini Elena, Nikitin Kirill, Stolarczyk Jacek K., Fitzmaurice Donald: Electron Transfer and Switching in Rigid [2]Rotaxanes Adsorbed on TiO2 Nanoparticles. ChemPhysChem 2012, 13, 797. <https://doi.org/10.1002/cphc.201100903>
- Hansen Stinne W., Stein Paul C., Sørensen Anne, Share Andrew I., Witlicki Edward H., Kongsted Jacob, Flood Amar H., Jeppesen Jan O.: Quantification of the π–π Interactions that Govern Tertiary Structure in Donor–Acceptor [2]Pseudorotaxanes. J. Am. Chem. Soc. 2012, 134, 3857. <https://doi.org/10.1021/ja210861v>
- Coskun Ali, Spruell Jason M., Barin Gokhan, Dichtel William R., Flood Amar H., Botros Youssry Y., Stoddart J. Fraser: High hopes: can molecular electronics realise its potential?. Chem. Soc. Rev. 2012, 41, 4827. <https://doi.org/10.1039/c2cs35053j>
- Credi Alberto, Semeraro Monica, Silvi Serena, Venturi Margherita: Redox Control of Molecular Motion in Switchable Artificial Nanoscale Devices. Antioxidants & Redox Signaling 2011, 14, 1119. <https://doi.org/10.1089/ars.2010.3223>
- Nielsen Kent A., Levillain Eric, Lynch Vincent M., Sessler Jonathan L., Jeppesen Jan O.: Tetrathiafulvalene Porphyrins. Chemistry A European J 2009, 15, 506. <https://doi.org/10.1002/chem.200801636>
- Kim Hyungjun, Goddard William A., Jang Seung Soon, Dichtel William R., Heath James R., Stoddart J. Fraser: Free Energy Barrier for Molecular Motions in Bistable [2]Rotaxane Molecular Electronic Devices. J. Phys. Chem. A 2009, 113, 2136. <https://doi.org/10.1021/jp809213m>
- Canevet David, Sallé Marc, Zhang Guanxin, Zhang Deqing, Zhu Daoben: Tetrathiafulvalene (TTF) derivatives: key building-blocks for switchable processes. Chem. Commun. 2009, 2245. <https://doi.org/10.1039/b818607n>
- Lestini Elena, Nikitin Kirill, Müller‐Bunz Helge, Fitzmaurice Donald: Introducing Negative Charges into Bis‐p‐phenylene Crown Ethers: A Study of Bipyridinium‐Based [2]Pseudorotaxanes and [2]Rotaxanes. Chemistry A European J 2008, 14, 1095. <https://doi.org/10.1002/chem.200700387>
- Altobello Silvano, Nikitin Kirill, Stolarczyk Jacek K., Lestini Elena, Fitzmaurice Donald: Quantitative Conformational Study of Redox‐Active [2]Rotaxanes, Part 1: Methodology and Application to a Model [2]Rotaxane. Chemistry A European J 2008, 14, 1107. <https://doi.org/10.1002/chem.200700898>
- Nikitin Kirill, Lestini Elena, Stolarczyk Jacek K., Müller‐Bunz Helge, Fitzmaurice Donald: Quantitative Conformational Study of Redox‐Active [2]Rotaxanes, Part 2: Switching in Flexible and Rigid Bistable [2]Rotaxanes. Chemistry A European J 2008, 14, 1117. <https://doi.org/10.1002/chem.200701384>
- Aprahamian Ivan, Olsen John‐Carl, Trabolsi Ali, Stoddart J. Fraser: Tetrathiafulvalene Radical Cation Dimerization in a Bistable Tripodal [4]Rotaxane. Chemistry A European J 2008, 14, 3889. <https://doi.org/10.1002/chem.200800191>
- Stoddart J. Fraser, Colquhoun Howard M.: Big and little Meccano. Tetrahedron 2008, 64, 8231. <https://doi.org/10.1016/j.tet.2008.06.035>
- Guo X., Zhou Y., Feng M., Xu Y., Zhang D., Gao H., Fan Q., Zhu D.: Tetrathiafulvalene‐, 1,5‐Dioxynaphthalene‐, and Cyclobis(paraquat‐p‐phenylene)‐based [2]Rotaxanes with Cyclohexyl and Alkyl Chains as Spacers: Synthesis, Langmuir–Blodgett Films, and Electrical Bistability. Adv Funct Materials 2007, 17, 763. <https://doi.org/10.1002/adfm.200600898>
- Nygaard S., Liu Y., Stein P. C., Flood A. H., Jeppesen J. O.: Using Molecular Force to Overcome Steric Barriers in a Springlike Molecular Ouroboros**. Adv Funct Materials 2007, 17, 751. <https://doi.org/10.1002/adfm.200600907>
- Aprahamian Ivan, Yasuda Takuma, Ikeda Taichi, Saha Sourav, Dichtel William R., Isoda Kyosuke, Kato Takashi, Stoddart J. Fraser: A Liquid‐Crystalline Bistable [2]Rotaxane. Angewandte Chemie 2007, 119, 4759. <https://doi.org/10.1002/ange.200700305>
- Aprahamian Ivan, Yasuda Takuma, Ikeda Taichi, Saha Sourav, Dichtel William R., Isoda Kyosuke, Kato Takashi, Stoddart J. Fraser: A Liquid‐Crystalline Bistable [2]Rotaxane. Angew Chem Int Ed 2007, 46, 4675. <https://doi.org/10.1002/anie.200700305>
- Nygaard Sune, Leung Ken C.-F., Aprahamian Ivan, Ikeda Taichi, Saha Sourav, Laursen Bo W., Kim Soo-Young, Hansen Stinne W., Stein Paul C., Flood Amar H., Stoddart J. Fraser, Jeppesen Jan O.: Functionally Rigid Bistable [2]Rotaxanes. J. Am. Chem. Soc. 2007, 129, 960. <https://doi.org/10.1021/ja0663529>
- Nygaard Sune, Hansen Stinne W., Huffman John C., Jensen Frank, Flood Amar H., Jeppesen Jan O.: Two Classes of Alongside Charge-Transfer Interactions Defined in One [2]Catenane. J. Am. Chem. Soc. 2007, 129, 7354. <https://doi.org/10.1021/ja069047w>
- Saha Sourav, Flood Amar H., Stoddart J. Fraser, Impellizzeri Stefania, Silvi Serena, Venturi Margherita, Credi Alberto: A Redox-Driven Multicomponent Molecular Shuttle. J. Am. Chem. Soc. 2007, 129, 12159. <https://doi.org/10.1021/ja0724590>
- Nygaard Sune, Hansen Camilla N., Jeppesen Jan O.: Binding Studies between Triethylene Glycol-Substituted Monopyrrolotetrathiafulvalene Derivatives and Cyclobis(paraquat-p-phenylene). J. Org. Chem. 2007, 72, 1617. <https://doi.org/10.1021/jo061962c>
- Nikitin Kirill, Lestini Elena, Lazzari Mariachiara, Altobello Silvano, Fitzmaurice Donald: A Tripodal [2]Rotaxane on the Surface of Gold. Langmuir 2007, 23, 12147. <https://doi.org/10.1021/la701657r>
- Aprahamian Ivan, Dichtel William R., Ikeda Taichi, Heath James R., Stoddart J. Fraser: A Clicked Bistable [2]Rotaxane. Org. Lett. 2007, 9, 1287. <https://doi.org/10.1021/ol070052u>
- Murakami Hiroto, Chifu Hiroko, Sagara Takamasa: Fabrication of a Self-assembled Rotaxane Monolayer Consisting of a Viologen-functionalized Alkanethiol and α-Cyclodextrin Using Potential Sweep Method. Chemistry Letters 2007, 36, 1218. <https://doi.org/10.1246/cl.2007.1218>
- Choi Jang Wook, Flood Amar H., Steuerman David W., Nygaard Sune, Braunschweig Adam B., Moonen Nicolle N. P., Laursen Bo W., Luo Yi, DeIonno Erica, Peters Andrea J., Jeppesen Jan O., Xu Ke, Stoddart J. Fraser, Heath James R.: Ground‐State Equilibrium Thermodynamics and Switching Kinetics of Bistable [2]Rotaxanes Switched in Solution, Polymer Gels, and Molecular Electronic Devices. Chemistry A European J 2006, 12, 261. <https://doi.org/10.1002/chem.200500934>
- Flood Amar H., Wong Eric W., Stoddart J. Fraser: Models of charge transport and transfer in molecular switch tunnel junctions of bistable catenanes and rotaxanes. Chemical Physics 2006, 324, 280. <https://doi.org/10.1016/j.chemphys.2005.12.031>
- Flood Amar H., Nygaard Sune, Laursen Bo W., Jeppesen Jan O., Stoddart J. Fraser: Locking down the Electronic Structure of (Monopyrrolo)tetrathiafulvalene in [2]Rotaxanes. Org. Lett. 2006, 8, 2205. <https://doi.org/10.1021/ol060319+>
- Vella Sarah J., Tiburcio Jorge, Gauld James W., Loeb Stephen J.: Push−Pull [2]Pseudorotaxanes. Electronic Control of Threading by Switching ON/OFF an Intramolecular Charge Transfer. Org. Lett. 2006, 8, 3421. <https://doi.org/10.1021/ol0610338>
- Beckman Robert, Beverly Kris, Boukai Akram, Bunimovich Yuri, Choi Jang Wook, DeIonno Erica, Green Johnny, Johnston-Halperin Ezekiel, Luo Yi, Sheriff Bonnie, Stoddart J. Fraser, Heath James R.: Spiers Memorial Lecture : Molecular mechanics and molecular electronics. Faraday Discuss. 2006, 131, 9. <https://doi.org/10.1039/B513148K>
- Nørgaard Kasper, Laursen Bo W., Nygaard Sune, Kjaer Kristian, Tseng Hsian‐Rong, Flood Amar H., Stoddart J. Fraser, Bjørnholm Thomas: Structural Evidence of Mechanical Shuttling in Condensed Monolayers of Bistable Rotaxane Molecules. Angewandte Chemie 2005, 117, 7197. <https://doi.org/10.1002/ange.200501538>
- Nørgaard Kasper, Laursen Bo W., Nygaard Sune, Kjaer Kristian, Tseng Hsian‐Rong, Flood Amar H., Stoddart J. Fraser, Bjørnholm Thomas: Structural Evidence of Mechanical Shuttling in Condensed Monolayers of Bistable Rotaxane Molecules. Angew Chem Int Ed 2005, 44, 7035. <https://doi.org/10.1002/anie.200501538>
- Liu Yi, Flood Amar H., Moskowitz Ross M., Stoddart J. Fraser: Versatile Self‐Complexing Compounds Based on Covalently Linked Donor–Acceptor Cyclophanes. Chemistry A European J 2005, 11, 369. <https://doi.org/10.1002/chem.200400614>
- Jang Seung Soon, Jang Yun Hee, Kim Yong-Hoon, Goddard William A., Flood Amar H., Laursen Bo W., Tseng Hsian-Rong, Stoddart J. Fraser, Jeppesen Jan O., Choi Jang Wook, Steuerman David W., DeIonno Erica, Heath James R.: Structures and Properties of Self-Assembled Monolayers of Bistable [2]Rotaxanes on Au (111) Surfaces from Molecular Dynamics Simulations Validated with Experiment. J. Am. Chem. Soc. 2005, 127, 1563. <https://doi.org/10.1021/ja044530x>
- Jang Yun Hee, Jang Seung Soon, Goddard William A.: Molecular Dynamics Simulation Study on a Monolayer of Half [2]Rotaxane Self-Assembled on Au(111). J. Am. Chem. Soc. 2005, 127, 4959. <https://doi.org/10.1021/ja044762w>
- Liu Yi, Flood Amar H., Bonvallet Paul A., Vignon Scott A., Northrop Brian H., Tseng Hsian-Rong, Jeppesen Jan O., Huang Tony J., Brough Branden, Baller Marko, Magonov Sergei, Solares Santiago D., Goddard William A., Ho Chih-Ming, Stoddart J. Fraser: Linear Artificial Molecular Muscles. J. Am. Chem. Soc. 2005, 127, 9745. <https://doi.org/10.1021/ja051088p>
- Jang Seung Soon, Jang Yun Hee, Kim Yong-Hoon, Goddard William A., Choi Jang Wook, Heath James R., Laursen Bo W., Flood Amar H., Stoddart J. Fraser, Nørgaard Kasper, Bjørnholm Thomas: Molecular Dynamics Simulation of Amphiphilic Bistable [2]Rotaxane Langmuir Monolayers at the Air/Water Interface. J. Am. Chem. Soc. 2005, 127, 14804. <https://doi.org/10.1021/ja0531531>
- Nørgaard Kasper, Jeppesen Jan O., Laursen Bo W., Simonsen Jens B., Weygand Markus J., Kjaer Kristian, Stoddart J. Fraser, Bjørnholm Thomas: Evidence of Strong Hydration and Significant Tilt of Amphiphilic [2]Rotaxane Molecules in Langmuir Films Studied by Synchrotron X-ray Reflectivity. J. Phys. Chem. B 2005, 109, 1063. <https://doi.org/10.1021/jp0448494>
- Agrawal, Y.K., Sharma, C.R.: Supramolecular Assemblies and their Applications. REVAC 2005, 24, 35. <https://doi.org/10.1515/REVAC.2005.24.1.35>
- Steuerman David W., Tseng Hsian‐Rong, Peters Andrea J., Flood Amar H., Jeppesen Jan O., Nielsen Kent A., Stoddart J. Fraser, Heath James R.: Molecular‐Mechanical Switch‐Based Solid‐State Electrochromic Devices. Angewandte Chemie 2004, 116, 6648. <https://doi.org/10.1002/ange.200461723>
- Steuerman David W., Tseng Hsian‐Rong, Peters Andrea J., Flood Amar H., Jeppesen Jan O., Nielsen Kent A., Stoddart J. Fraser, Heath James R.: Molecular‐Mechanical Switch‐Based Solid‐State Electrochromic Devices. Angew Chem Int Ed 2004, 43, 6486. <https://doi.org/10.1002/anie.200461723>
- Kang Seogshin, Vignon Scott A., Tseng Hsian‐Rong, Stoddart J. Fraser: Molecular Shuttles Based on Tetrathiafulvalene Units and 1,5‐Dioxynaphthalene Ring Systems. Chemistry A European J 2004, 10, 2555. <https://doi.org/10.1002/chem.200305725>
- Iijima Takahiro, Vignon Scott A., Tseng Hsian‐Rong, Jarrosson Thibaut, Sanders Jeremy K. M., Marchioni Filippo, Venturi Margherita, Apostoli Emanuela, Balzani Vincenzo, Stoddart J. Fraser: Controllable Donor–Acceptor Neutral [2]Rotaxanes. Chemistry A European J 2004, 10, 6375. <https://doi.org/10.1002/chem.200400651>
- Tseng Hsian‐Rong, Wu Dongmin, Fang Nicholas Xuanlai, Zhang Xiang, Stoddart J. Fraser: The Metastability of an Electrochemically Controlled Nanoscale Machine on Gold Surfaces. ChemPhysChem 2004, 5, 111. <https://doi.org/10.1002/cphc.200300992>
- Jang Yun Hee, Hwang Sungu, Kim Yong-Hoon, Jang Seung Soon, Goddard William A.: Density Functional Theory Studies of the [2]Rotaxane Component of the Stoddart−Heath Molecular Switch. J. Am. Chem. Soc. 2004, 126, 12636. <https://doi.org/10.1021/ja0385437>
- Lee Isaac C., Frank Curtis W., Yamamoto Tohru, Tseng Hsian-Rong, Flood Amar H., Stoddart J. Fraser, Jeppesen Jan O.: Langmuir and Langmuir−Blodgett Films of Amphiphilic Bistable Rotaxanes. Langmuir 2004, 20, 5809. <https://doi.org/10.1021/la0361518>
- Laursen Bo W., Nygaard Sune, Jeppesen Jan O., Stoddart J. Fraser: Counterion-Induced Translational Isomerism in a Bistable [2]Rotaxane. Org. Lett. 2004, 6, 4167. <https://doi.org/10.1021/ol048518l>