Abstract
The mechanical bond offers novel and intriguing opportunities to connect together molecular components and arrange them in space. Mechanically interlocked molecules (MIMs) such as rotaxanes and catenanes can indeed be designed to operate as molecular devices, that is, to accomplish function(s) that arise(s) from the cooperation of their molecular components. In this chapter we will deal with rotaxane- and catenane-based architectures characterized by two main features: (i) the presence of inorganic moieties in the molecular structure and (ii) the integration of photoactive units. Here we focus on metal complexes as inorganic moieties, which can play the dual role of scaffolds for the construction of the molecules and for controlling the spatial arrangement of the components, and of functional units, because they present peculiar photophysical and electrochemical properties. The use of light to operate molecular devices and machines has long been acknowledged as a most valuable choice under several aspects. In this regard, for the sake of clarity, we have classified the selected examples in two main categories: photoactive systems, which are characterized by photoinduced processes within the components of the interlocked architecture, and photoactivated systems, wherein light is used to cause a mechanical rearrangement of the components. The examples discussed will show how the union of the structural control offered by the mechanical bond with the tools of inorganic chemistry can lead to the realization of complex structures with sophisticated functions.
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References
Bruns, C.J., Stoddart, J.F.: The Nature of the Mechanical Bond. Wiley, Hoboken (2017)
Sauvage, J.-P., Dietrich-Buchecker, C.: Molecular Catenanes, Rotaxanes and Knots. Wiley-VCH, Weinheim (1999)
Ashton, P.R., Baxter, I., Fyfe, M.C.T., et al.: Rotaxane or Pseudorotaxane? That Is the Question! J. Am. Chem. Soc. 120, 2297–2397 (1998)
Balzani, V., Venturi, M., Credi, A.: Molecular Devices and Machines: A Journey Into the Nanoworld, 2nd edn. Wiley-VCH, Weinheim (2008)
(a) Balzani, V., Credi, A., Venturi, M.: Light powered molecular machines. Chem. Soc. Rev. 38, 1542–1550 (2009); (b) Silvi, S., Venturi, M., Credi, A.: Light operated molecular machines. Chem. Commun. 47, 2483–2489 (2011); (c) Ceroni, P., Credi, A., Venturi, M.: Light to investigate (read) and operate (write) molecular devices and machines. Chem. Soc. Rev. 43, 4068–4083 (2014)
Ceroni, P., Balzani, V., Juris, A.: Photochemistry and Photophysics: Concepts, Research, Applications. Wiley-VCH, Weinheim (2014)
(a) Dietrich-Buchecker, C.O., Sauvage, J-P.: Une nouvelle famille de molecules : les metallo-catenanes. Tetrahedron Lett. 24, 5095–5098 (1983); (b) Dietrich-Buchecker, C.O., Sauvage, J.P., Kern, J.M.: Templated synthesis of interlocked macrocyclic ligands: the catenands. J. Am. Chem. Soc. 106, 3043–3045 (1984); (c) Dietrich-Buchecker, C.O., Sauvage, J.P.: Interlocking of molecular threads: from the statistical approach to the templated synthesis of catenands. Chem. Rev. 87, 795–810 (1987)
Sauvage, J.P.: From Chemical Topology to Molecular Machines (Nobel Lecture). Angew. Chem. Int. Ed. 56, 11080–11093 (2017)
Van Gaal, H.L.M., Van Der Linden, J.G.M.: Trends in redox potentials of transition metal complexes. Coord. Chem. Rev. 47, 41–54 (1982)
Juris, A., Balzani, V., Barigelletti, F., et al.: Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence. Coord. Chem. Rev. 84, 85–277 (1988)
Campagna, S., Puntoriero, F., Nastasi, F., et al.: Photochemistry and Photophysics of Coordination Compounds: Ruthenium. Top. Curr. Chem. 280, 117–214 (2007)
Kadish, K.M., Smith, K.M., Guilard, R. (eds.): The Porphyrin Handbook. Academic Press, New York (1999)
Andersson, M., Lynke, M., Chambron, J.-C., et al.: Porphyrin-containing [2]-Rotaxanes: Metal Coordination Enhanced Superexchange Electron Transfer between Noncovalently Linked Chromophores. J. Am. Chem. Soc. 122, 3526–3527 (2000)
Andersson, M., Lynke, M., Chambron, J.-C., et al.: Long-Range Electron Transfer in Porphyrin-Containing [2]-Rotaxanes: Tuning the Rate by Metal Cation Coordination. J. Am. Chem. Soc. 124, 4347–4362 (2002)
Echegoyen, L., Echegoyen, L.E.: Electrochemistry of Fullerenes and Their Derivatives. Acc. Chem. Res. 31, 593–601 (1998)
Guldi, D.M.: Fullerene–porphyrin architectures; photosynthetic antenna and reaction center models. Chem. Soc. Rev. 31, 22–36 (2002)
Zhang, G., Gil-Ramírez, G., Markevicius, A., et al.: Lanthanide Template Synthesis of Trefoil Knots of Single Handedness. J. Am. Chem. Soc. 137, 10437–10442 (2015)
(a) Bünzli, J.C.G., Piguet, C.: Taking advantage of luminescent lanthanide ions. Chem. Soc. Rev. 34, 1048–1077 (2005); (b) Armelao, L., Quici, S., Barigelletti, F., et al.: Design of luminescent lanthanide complexes: From molecules to highly efficient photo-emitting materials. Coord. Chem. Rev. 254, 487–505 (2010)
Lynke, M., Chambron, J.-C., Heinz, V., et al.: Electron Transfer between Mechanically Linked Porphyrins in a [2]Rotaxane. J. Am. Chem. Soc. 119, 11329–11330 (1997)
Megiatto, J.D., Schuster, D.I., De Miguel, G., et al.: Topological and Conformational Effects on Electron Transfer Dynamics in Porphyrin-[60]Fullerene Interlocked Systems. Chem. Mater. 24, 2472–2485 (2012)
Imahori, H., El-Khouly, M.E., Fujitsuka, M., et al.: Solvent Dependence of Charge Separation and Charge Recombination Rates in Porphyrin−Fullerene Dyad. J. Phys. Chem. A. 105, 325–332 (2001)
(a) Rajkumar, G.A., Sandanayaka, A.S.D., Ikeshita, K., et al.: Prolongation of the Lifetime of the Charge-Separated State at Low Temperatures in a Photoinduced Electron-Transfer System of [60]Fullerene and Ferrocene Moieties Tethered by Rotaxane Structures. J. Phys. Chem. B 110, 6516–6525 (2006); (b) Marois, J-S., Cantin, K., Desmarais, A., Morin, J-F.: [3]Rotaxane−Porphyrin Conjugate as a Novel Supramolecular Host for Fullerenes. Org. Lett. 10, 33–36 (2008)
Watanabe, N., Kihara, N., Furusho, Y., et al.: Photoinduced Intrarotaxane Electron Transfer between Zinc Porphyrin and [60]Fullerene in Benzonitrile. Angew. Chem. Int. Ed. 42, 681–683 (2003)
Li, K., Schuster, D.I., Guldi, D.M., et al.: Convergent Synthesis and Photophysics of [60]Fullerene/Porphyrin-Based Rotaxanes. J. Am. Chem. Soc. 126, 3388–3389 (2004)
Jakob, M., Berg, A., Rubin, R., et al.: Photoinduced Electron Transfer in Porphyrin- and Fullerene/Porphyrin-Based Rotaxanes as Studied by Time-Resolved EPR Spectroscopy. J. Phys. Chem. A. 113, 5846–5854 (2009)
Li, K., Bracher, P.J., Guldi, D.M., et al.: [60]Fullerene-Stoppered Porphyrinorotaxanes: Pronounced Elongation of Charge-Separated-State Lifetimes. J. Am. Chem. Soc. 126, 9156–9157 (2004)
Armaroli, N., Diederich, F., Dietrich-Buchecker, C.O., et al.: A Copper(I)-Complexed Rotaxane with Two Fullerene Stoppers: Synthesis, Electrochemistry, and Photoinduced Processes. Chem. Eur. J. 4, 406–416 (1998)
Kirner, S.V., Henkel, C., Guldi, D.M., et al.: Multistep energy and electron transfer processes in novel rotaxane donor–acceptor hybrids generating microsecond-lived charge separated states. Chem. Sci. 6, 7293–7304 (2015)
(a) Megiatto, J.D., Spencer, R., Schuster, D.I.: Efficient One-Pot Synthesis of Rotaxanes Bearing Electron Donors and [60]Fullerene. Org. Lett. 11, 4152–4155 (2009); (b) Megiatto, J.D., Spencer, R., Schuster, D.I.: Optimizing reaction conditions for synthesis of electron donor-[60]fullerene interlocked multiring systems. J. Mater. Chem. 21, 1544–1550 (2011)
Lynke, M., Chambron, J.-C., Heinz, V., et al.: Multiporphyrinic Rotaxanes: Control of Intramolecular Electron Transfer Rate by Steering the Mutual Arrangement of the Chromophores. J. Am. Chem. Soc. 122, 11834–11844 (2000)
Megiatto, J.D., Schuster, D.I., Abwandner, S., et al.: [2]Catenanes Decorated with Porphyrin and [60]Fullerene Groups: Design, Convergent Synthesis, and Photoinduced Processes. J. Am. Chem. Soc. 132, 3847–3861 (2010)
Flaigni, L., Talarico, A.M., Chambron, J.-C., et al.: Photoinduced Electron Transfer in Multiporphyrinic Interlocked Structures: The Effect of Copper(I) Coordination in the Central Site. Chem. Eur. J. 10, 2689–2699 (2004)
Albrecht-Gary, A.M., Saad, Z., Dietrich-Buchecker, C.O., Sauvage, J.P.: Interlocked macrocyclic ligands: a kinetic catenand effect in copper(I) complexes. J. Am. Chem. Soc. 107, 3205–3209 (1985)
Ferrer, B., Rogez, G., Credi, A., et al.: Photoinduced electron flow in a self-assembling supramolecular extension cable. Proc. Natl. Acad. Sci. U. S. A. 103, 18411–18416 (2006)
Flamigni, L., Armaroli, N., Barigelletti, F., et al.: Photoinduced processes in porphyrin-stoppered [3]-rotaxanes. New J. Chem. 23, 1151–1158 (1999)
Trolez, Y., Finke, A.D., Silvestri, F., et al.: Unconventional Synthesis of a CuI Rotaxane with a Superacceptor Stopper: Ultrafast Excited-State Dynamics and Near-Infrared Luminescence. Chem. Eur. J. 24, 10422–10433 (2018)
Delavaux-Nicot, B., Ben Aziza, H., Nierengarten, I., et al.: A Rotaxane Scaffold for the Construction of Multiporphyrinic Light-Harvesting Devices. Chem. Eur. J. 24, 133–140 (2018)
Maeda, C., Yamaguchi, S., Ikeda, C., et al.: Dimeric Assemblies from 1,2,3-Triazole-Appended Zn(II) Porphyrins with Control of NH-Tautomerism in 1,2,3-Triazole. Org. Lett. 10, 549–552 (2008)
Trinh, T.M.N., Nierengarten, I., Ben Aziza, H., et al.: Coordination-Driven Folding in Multi-ZnII-Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold. Chem. Eur. J. 23, 11011–11021 (2017)
Han, M., Zhang, H.-Y., Yang, L.-X., et al.: A Reversible Luminescent Lanthanide Switch Based on a Dibenzo[24]-Crown-8−Dipicolinic Acid Conjugate. Org. Lett. 10, 5557–5560 (2008)
Ding, Z.-J., Zhang, Y.-M., Teng, X., Liu, Y.: Controlled Photophysical Behaviors between Dibenzo-24-crown-8 Bearing Terpyridine Moiety and Fullerene-Containing Ammonium Salt. J. Org. Chem. 76, 1910–1913 (2011)
Erbas-Cakmak S., Leigh, D.A., McTernan, C.T., et al.: Artificial Molecular Machines. Chem. Rev. 115, 10081–10206 (2015)
(a) Everly, R.M., McMillin, D.R.: Reinvestigation of the absorbing and emitting charge-transfer excited states of [Cu(NN)2]+ systems. J. Phys. Chem. 95, 9071–9075 (1991); (b) Gushurst, A.K.I., McMillin, D.R., Dietrich-Buchecker, C.O., Sauvage, J.P.: Comparative studies of the photophysical properties of copper phenanthrolines: from Cu(dmp)2+ to the copper(I) catenates. Inorg. Chem. 28, 4070–4072 (1989); (c) Ruthkosky, M., Castellano, F.N., Meyer, G.J.: Photodriven Electron and Energy Transfer from Copper Phenanthroline Excited States. Inorg. Chem. 35, 6406–6412 (1996)
Livoreil, A., Sauvage, J.-P., Armaroli, N., et al.: Electrochemically and Photochemically Driven Ring Motions in a Disymmetrical Copper [2]-Catenate. J. Am. Chem. Soc. 119, 12114–12124 (1997)
Armaroli, N., Balzani, V., Collin, J.-P., et al.: Rotaxanes Incorporating Two Different Coordinating Units in Their Thread: Synthesis and Electrochemically and Photochemically Induced Molecular Motions. J. Am. Chem. Soc. 121, 4397–4408 (1999)
Kelly, L.A., Rodgers, M.A.J.: Inter- and Intramolecular Oxidative Quenching of Mixed Ligand Tris(bipyridyl)ruthenium(II) Complexes by Methyl Viologen. J. Phys. Chem. 99, 13132–13140 (1995)
Anelli, P.L., Ashton, P.R., Ballardini, R., et al.: Molecular meccano. 1. [2]Rotaxanes and a [2]catenane made to order. J. Am. Chem. Soc. 114, 193–218 (1992)
Ashton, P.R., Ballardini, R., Balzani, V., et al.: A Photochemically Driven Molecular-Level Abacus. Chem. Eur. J. 6, 3558–3574 (2000)
Balzani, V., Clemente-León, M., Credi, A., et al.: Autonomous artificial nanomotor powered by sunlight. Proc. Natl. Acad. Sci. U. S. A. 103, 1178–1183 (2006)
Scarpantonio, L., Tron, A., Destribats, C., et al.: Concatenation of reversible electronic energy transfer and photoinduced electron transfer to control a molecular piston. Chem. Commun. 48, 3981–3983 (2012)
Ashton, P.R., Balzani, V., Kocian, O., et al.: A Light-Fueled “Piston Cylinder” Molecular-Level Machine. J. Am. Chem. Soc. 120, 11190–11191 (1998)
Ford, W.E., Rodgers, M.A.J.: Reversible triplet-triplet energy transfer within a covalently linked bichromophoric molecule. J. Phys. Chem. 96, 2917–2920 (1992)
Qu, D.H., Tian, H.: Novel and efficient templates for assembly of rotaxanes and catenanes. Chem. Sci. 2, 1011–1015 (2011)
Trabolsi, A., Khashab, N., Fahrenbach, A.C., et al.: Radically enhanced molecular recognition. Nat. Chem. 2, 42–49 (2010)
Li, H., Fahrenbach, A.C., Dey, S.K., et al.: Mechanical Bond Formation by Radical Templation. Angew. Chem. Int. Ed. 49, 8260–8265 (2010)
Li, H., Fahrenbach, A.C., Coskun, A., et al.: A Light-Stimulated Molecular Switch Driven by Radical–Radical Interactions in Water. Angew. Chem. Int. Ed. 50, 6782–6788 (2011)
Sun, J., Wu, Y., Liu, Z., et al.: Visible Light-Driven Artificial Molecular Switch Actuated by Radical–Radical and Donor–Acceptor Interactions. J. Phys. Chem. A. 119, 6317–6325 (2015)
Jeon, W.S., Kim, H.-J., Lee, C., et al.: Control of the stoichiometry in host–guest complexation by redox chemistry of guests: Inclusion of methylviologen in cucurbit[8]uril. Chem. Commun. 0, 1828–1829 (2002)
Monhaphol, T.K., Andersson, S., Sun, L.: Isolated Supramolecular [Ru(bpy)3]–Viologen–[Ru(bpy)3] Complexes with Trapped CB[7,8] and Photoinduced Electron-Transfer Study in Nonaqueous Solution. Chem. Eur. J. 17, 11604–11612 (2011)
Barigelletti, F., Juris, A., Balzani, V., et al.: Excited-State Properties of Complexes of the Ru(diimine)32+ Family. Inorg. Chem. 22, 3335–3339 (1983)
Collin, J.-P., Jouvenot, D., Koizumi, M., et al.: A Ruthenium(II)-Complexed Rotaxane Whose Ring Incorporates a 6,6′-Diphenyl-2,2′-bipyridine: Synthesis and Light-Driven Motions. Eur. J. Inorg. Chem. 2005, 1850–1855 (2005)
Mobian, P., Kern, J.M., Sauvage, J.P.: Light-Driven Machine Prototypes Based on Dissociative Excited States: Photoinduced Decoordination and Thermal Recoordination of a Ring in a Ruthenium(II)-Containing [2]Catenane. Angew. Chem. Int. Ed. 43, 2392–2395 (2004)
Schäfer, C., Ragazzon, G., Colasson, B., et al.: An Artificial Molecular Transporter. Chem. Open. 5, 120–124 (2016)
Hecker, C.R., Fanwick, P.E., McMillin, D.R.: Evidence for Dissociative Photosubstitution Reactions of [Ru(trpy)(bpy)(NCCH3)]2+. Crystal and Molecular Structure of [Ru(trpy)(bpy)(py)](PF6)2·(CH3)2CO. Inorg. Chem. 30, 659–666 (1991)
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Baroncini, M., Canton, M., Casimiro, L., Credi, A., Silvi, S. (2022). Mechanically Interlocked Systems: Photoactive Rotaxanes and Catenanes. In: Bahnemann, D., Patrocinio, A.O.T. (eds) Springer Handbook of Inorganic Photochemistry. Springer Handbooks. Springer, Cham. https://doi.org/10.1007/978-3-030-63713-2_22
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