Abstract
Macrocycles, as a class of cyclic molecules, have been broadly researched by supramolecular chemists due to their efficient dynamic binding behaviors with suitable guest molecules. When the macrocycle and its corresponding guest were covalently tied up, an ingenious topological architecture named as “mechanically self-locked molecule” formed. Mechanically self-locked molecules using noncovalent interaction as driving force were designed and engineered at molecular resolution, providing a possibility to realize the motion of molecular machine in one molecule. On the basis of the number and position of the covalent connected sites between the macrocycle and the guest molecule, we will summarize the mechanically self-locked architectures according to the following categories: pseudo[1]rotaxanes, pseudo[1]catenanes, molecular figures-of-eight, pretzelanes, and double-lasso molecules. We wish this chapter focusing on the progress of these unique structures could expand the horizon for people who are interested in or working on the mechanically self-locked architectures or molecular machines.
References
Corey EJ, Cheng XM (1989) The logic of chemical synthesis. Wiley, New York
Nicolaou KC, Vourloumis D, Winssinger N, Baran PS (2000) The art and science of total synthesis at the dawn of the twenty-first century. Angew Chem Int Ed 39:44–122
Eaton PE, Cole TW (1964) Cubane. J Am Chem Soc 86:3157–3158
Wasserman E (1960) The preparation of interlocking rings: a catenane1. J Am Chem Soc 82:4433–4434
Frisch HL, Wasserman E (1961) Chemical topology1. J Am Chem Soc 83:3789–3795
Dietrich-Buchecker CO, Sauvage JP, Kintzinger JP (1983) Une nouvelle famille de molecules: Les metallo-catenanes. Tetrahedron Lett 24:5095–5098
Hubin TJ, Busch DH (2000) Template routes to interlocked molecular structures and orderly molecular entanglements. Coord Chem Rev 200–202:5–52
Reuter C, Mohry A, Sobanski A, Vögtle F (2000) [1]rotaxanes and pretzelanes: synthesis, chirality, and absolute configuration. Chem Eur J 6:1674–1682
Ashton PR, Ballardini R, Balzani V, Boyd SE, Credi A, Gandolfi MT, Gómez-López M, Iqbal S, Philp D, Preece JA, Prodi L, Ricketts HG, Stoddart JF, Tolley MS, Venturi M, Venturi M, White AJP, Williams DJ (1997) Simple mechanical molecular and supramolecular machines: photochemical and electrochemical control of switching processes. Chem Eur J 3:152–170
Ashton PR, Gómez-López M, Iqbal S, Preece JA, Stoddart JF (1997) A self-complexing macrocycle acting as a chromophoric receptor. Tetrahedron Lett 38:3635–3638
Liu Y, Flood AH, Moskowitz RM, Stoddart JF (2005) Versatile self-complexing compounds based on covalently linked donor–acceptor cyclophanes. Chem Eur J 11:369–385
Wang Y, Sun J, Liu Z, Nassar MS, Botros YY, Stoddart JF (2017) Radically promoted formation of a molecular lasso. Chem Sci 8:2562–2568
Brøndsted Nielsen M, Becher J (1998) ‘Self-complexing’ tetrathiafulvalene macrocycles; a tetrathiafulvalene switch. Chem Commun 475–476
Brøndsted Nielsen M, Hansen JG, Becher J (1999) Self-complexing tetrathiafulvalene-based donor–acceptor macrocycles. Eur J Org Chem 1999:2807–2815
Cooke G, Woisel P, Bria M, Delattre F, Garety JF, Hewage SG, Rabani G, Rosair GM (2006) A tuneable self-complexing molecular switch. Org Lett 8:1423–1426
Hooley RJ, Rebek (2007) Self-complexed deep cavitands: alkyl chains coil into a nearby cavity. Org Lett 9:1179–1182
Du X-S, Wang C-Y, Jia Q, Deng R, Tian H-S, Zhang H-Y, Meguellati K, Yang Y-W (2017) Pillar[5]arene-based [1]rotaxane: high-yield synthesis, characterization and application in knoevenagel reaction. Chem Commun 53:5326–5329
Balzani V, Ceroni P, Credi A, Gómez-López M, Hamers C, Fraser Stoddart J, Wolf R (2001) Controlled dethreading/rethreading of a scorpion-like pseudorotaxane and a related macrobicyclic self-complexing system. New J Chem 25:25–31
Hiratani K, Kaneyama M, Nagawa Y, Koyama E, Kanesato M (2004) Synthesis of [1]rotaxane via covalent bond formation and its unique fluorescent response by energy transfer in the presence of lithium ion. J Am Chem Soc 126:13568–13569
Qu D-H, Feringa BL (2010) Controlling molecular rotary motion with a self-complexing lock. Angew Chem 122:1125–1128
Li H, Zhang H, Zhang Q, Zhang Q-W, Qu D-H (2012) A switchable ferrocene-based [1]rotaxane with an electrochemical signal output. Org Lett 14:5900–5903
Li H, Zhang J-N, Zhou W, Zhang H, Zhang Q, Qu D-H, Tian H (2013) Dual-mode operation of a bistable [1]rotaxane with a fluorescence signal. Org Lett 15:3070–3073
Li H, Li X, Ågren H, Qu D-H (2014) Two switchable star-shaped [1](n)rotaxanes with different multibranched cores. Org Lett 16:4940–4943
Waelès P, Clavel C, Fournel-Marotte K, Coutrot F (2015) Synthesis of triazolium-based mono- and tris-branched [1]rotaxanes using a molecular transporter of dibenzo-24-crown-8. Chem Sci 6:4828–4836
Xue Z, Mayer MF (2010) Actuator prototype: capture and release of a self-entangled [1]rotaxane. J Am Chem Soc 132:3274–3276
Ogawa T, Usuki N, Nakazono K, Koyama Y, Takata T (2015) Linear–cyclic polymer structural transformation and its reversible control using a rational rotaxane strategy. Chem Commun 51:5606–5609
Onagi H, Blake CJ, Easton CJ, Lincoln SF (2003) Installation of a ratchet tooth and pawl to restrict rotation in a cyclodextrin rotaxane. Chem Eur J 9:5978–5988
Ma X, Wang Q, Tian H (2007) Disparate orientation of [1]rotaxanes. Tetrahedron Lett 48:7112–7116
Ma X, Qu D, Ji F, Wang Q, Zhu L, Xu Y, Tian H (2007) A light-driven [1]rotaxane via self-complementary and suzuki-coupling capping. Chem Commun 1409–1411
Di Motta S, Avellini T, Silvi S, Venturi M, Ma X, Tian H, Credi A, Negri F (2013) Photophysical properties and conformational effects on the circular dichroism of an azobenzene–cyclodextrin [1]rotaxane and its molecular components. Chem Eur J 19:3131–3138
Cao J, Ma X, Min M, Cao T, Wu S, Tian H (2014) Inhibit logic operations based on light-driven β-cyclodextrin pseudo[1]rotaxane with room temperature phosphorescence addresses. Chem Commun 50:3224–3226
Franchi P, Fanì M, Mezzina E, Lucarini M (2008) Increasing the persistency of stable free-radicals: synthesis and characterization of a nitroxide based [1]rotaxane. Org Lett 10:1901–1904
Miyawaki A, Kuad P, Takashima Y, Yamaguchi H, Harada A (2008) Molecular puzzle ring: pseudo[1]rotaxane from a flexible cyclodextrin derivative. J Am Chem Soc 130:17062–17069
Yamauchi K, Miyawaki A, Takashima Y, Yamaguchi H, Harada A (2010) Switching from altro-α-cyclodextrin dimer to pseudo[1]rotaxane dimer through tumbling. Org Lett 12:1284–1286
Legros V, Vanhaverbeke C, Souard F, Len C, Désiré J (2013) Β-cyclodextrin–glycerol dimers: synthesis and NMR conformational analysis. Eur J Org Chem 2013:2583–2590
Gao C, Ma X, Zhang Q, Wang Q, Qu D, Tian H (2011) A light-powered stretch–contraction supramolecular system based on cobalt coordinated [1]rotaxane. Org Biomol Chem 9:1126–1132
Liu Y, Chipot C, Shao X, Cai W (2014) Threading or tumbling? Insight into the self-inclusion mechanism of an altro-α-cyclodextrin derivative. J Phys Chem C 118:19380–19386
Wolf R, Asakawa M, Ashton PR, Gómez-López M, Hamers C, Menzer S, Parsons IW, Spencer N, Stoddart JF, Tolley MS, Williams DJ (1998) A molecular chameleon: chromophoric sensing by a self-complexing molecular assembly. Angew Chem Int Ed 37:975–979
Ogoshi T, Akutsu T, Yamafuji D, Aoki T, Yamagishi T-a (2013) Solvent- and achiral-guest-triggered chiral inversion in a planar chiral pseudo[1]catenane. Angew Chem 125:8269–8273
Yao J, Wu W, Liang W, Feng Y, Zhou D, Chruma JJ, Fukuhara G, Mori T, Inoue Y, Yang C (2017) Temperature-driven planar chirality switching of a pillar[5]arene-based molecular universal joint. Angew Chem Int Ed 56:6869–6873
Lee E, Ju H, Park I-H, Jung JH, Ikeda M, Kuwahara S, Habata Y, Lee SS (2018) Pseudo[1]catenane-type pillar[5]thiacrown whose planar chiral inversion is triggered by metal cation and controlled by anion. J Am Chem Soc 140:9669–9677
Li S-H, Zhang H-Y, Xu X, Liu Y (2015) Mechanically selflocked chiral gemini-catenanes. Nat Commun 6:7590–7596
Reuter C, Wienand W, Schmuck C, Vögtle F (2001) A self-threaded “molecular 8”. Chem Eur J 7:1728–1733
Boyle MM, Forgan RS, Friedman DC, Gassensmith JJ, Smaldone RA, Stoddart JF, Sauvage J-P (2011) Donor–acceptor molecular figures-of-eight. Chem Commun 47:11870–11872
Boyle MM, Gassensmith JJ, Whalley AC, Forgan RS, Smaldone RA, Hartlieb KJ, Blackburn AK, Sauvage J-P, Stoddart JF (2012) Stereochemistry of molecular figures-of-eight. Chem Eur J 18:10312–10323
Liu Y, Vignon SA, Zhang X, Bonvallet PA, Khan SI, Houk KN, Stoddart JF (2005) Dynamic chirality in donor−acceptor pretzelanes. J Org Chem 70:9334–9344
Zhao Y-L, Trabolsi A, Stoddart JF (2009) A bistable pretzelane. Chem Commun 4844–4846
Han M, Zhang H-Y, Yang L-X, Ding Z-J, Zhuang R-J, Liu Y (2011) A [2]catenane and pretzelane based on sn–porphyrin and crown ether. Eur J Org Chem 2011:7271–7277
Romuald C, Ardá A, Clavel C, Jiménez-Barbero J, Coutrot F (2012) Tightening or loosening a pH-sensitive double-lasso molecular machine readily synthesized from an ends-activated [c2]daisy chain. Chem Sci 3:1851–1857
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Li, SH., Chen, Y., Liu, Y. (2019). Mechanically Self-Locked Molecules. In: Liu, Y., Chen, Y., Zhang, HY. (eds) Handbook of Macrocyclic Supramolecular Assembly . Springer, Singapore. https://doi.org/10.1007/978-981-13-1744-6_5-1
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DOI: https://doi.org/10.1007/978-981-13-1744-6_5-1
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