Keywords
Fullerenes
Supramolecular
Preorganization
Molecular devices
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Abstract
Non-planar polycyclic aromatic hydrocarbons (PAHs) are organic molecules characterized by an aromatic framework composed of multiple fused benzene rings, exclusively containing sp2 carbon atoms. These nonplanar PAHs exhibit enhanced properties over planar analogs, such as enhanced solubility and the ability to self-assemble, making them ideal components of new materials. The most notable member of the family is corannulene ([5]circulene, C20H10). The topology of corannulene and its complementarity with fullerenes is expected to play a significant role in supramolecular binding. Consequently, various molecular tweezers incorporating two or more corannulene units linked by different spacer groups have been reported. Herein, we highlight selected examples in supramolecular interactions.
References
J.-M. Lehn, Chem. Soc. Rev. 2017, 46, 2378-2379, https://doi.org/10.1039/C7CS00115K.
J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, John Wiley & Sons, 2011.
J.W. Steed, J. L. Atwood, Supramolecular Chemistry, John Wiley & Sons, 2022.
S. Erbas-Cakmak, D. A. Leigh, C. T. McTernan, A. L. Nussbaumer, Chem. Rev. 2015, 115(18), 10081-10206, https://doi.org/10.1021/acs.chemrev.5b00146.
K. Ariga, H. Ito, J.P. Hill, H. Tsukube, Chem. Soc. Rev. 2012, 41, 5800, https://doi.org/10.1039/C2CS35162E.
D. Pochan, O. Scherman, Chem. Rev. 2021, 121(22), 13699-13700, https://doi.org/10.1021/acs.chemrev.1c00884.
D.B. Amabilino, D.K. Smith, J.W. Steed, Chem. Soc. Rev. 2017, 46, 2404-2420, https://doi.org/10.1039/C7CS00163K.
J. Yu, M. Gaedke, F. Schaufelberger, Eur. J. Org. Chem. 2023, 26(8), e202201130, https://doi.org/10.1002/ejoc.202201130.
Z. Li, Z. Liu, H. Sun, C. Gao, Chem. Rev. 2015, 115(15), 7046-7117, https://doi.org/10.1021/acs.chemrev.5b00102.
V. Georgakilas, J.A. Perman, J. Tucek, R. Zboril, Chem. Rev. 2015, 115(11), 4744-4822, https://doi.org/10.1021/cr500304f.
K.S. Novoselov, A.K. Geim, S.V. Morozov, D. Jiang, Y. Zhang, S.V. Dubonos, I.V. Grigorieva, A.A. Firsov, Science 2004, 306, 666-669, https://doi.org/10.1126/science.1102896.
S. Iijima, T. Ichihashi, Nature 1993, 363, 603–605, https://doi.org/10.1038/363603a0.
S. Collavini, J.L. Delgado, Sustainable Energy Fuels 2018, 2, 2480-2493, https://doi.org/10.1039/C8SE00254A.
D.M. Guldi, M. Prato, Acc. Chem. Res. 2000, 33, 695-703, https://doi.org/10.1021/ar990144m.
C. Fuertes-Espinosa, M. Pujals, X. Ribas, Chem 2020, 6(12), 3219-3262, https://doi.org/10.1016/j.chempr.2020.11.003.
X. Chang, Y. Xu, M. von Delius, Chem. Soc. Rev. 2024, 53, 47-83, https://doi.org/10.1039/D2CS00937D.
C. Wang, H. Dong, W. Hu, Y. Liu, D. Zhu, Chem. Rev. 2012, 112(4), 2208-2267, https://doi.org/10.1021/cr100380z.
M. Rickhaus, M. Mayor, M. Juriček, Chem. Soc. Rev. 2017, 46, 1643-1660, https://doi.org/10.1039/C6CS00623J.
L. Ripani, E. Bombonato, F. Paolucci, M. Marcaccio, Curr. Opin. Electrochem. 2022, 35, 101065, https://doi.org/10.1016/j.coelec.2022.101065.
R.G. Lawton, W.W. Barth, J. Am. Chem. Soc. 1971, 93, 1730-1745, https://doi.org/10.1021/ja00736a028.
K. Yamamoto, T. Harada, M. Nakazaki, T. Naka, Y. Kai, S. Harada, N. Kasai, J. Am. Chem. Soc. 1983, 105(24), 7171-7172, https://doi.org/10.1021/ja00362a025.
Y. Shen, C.F. Chen, Chem. Rev. 2012, 112(3), 1463-1535, https://doi.org/10.1021/cr200087r.
S. Zank, J.M. Fernandez‐Garcia, A.J. Stasyuk, A.A. Voityuk, M. Krug, M. Sola, D.M. Guldi, N. Martin, Angew. Chem., Int. Ed. 2022, 61(7), 2-10, https://doi.org/10.1002/anie.202112834.
J.C. Hanson, C.E. Nordman, Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater. 1976, 32, 1147–1153, https://doi.org/10.1107/S0567740876012430.
F.J. Lovas, R.J. McMahon, J.-U. Grabow, M. Schnell, J. Mack, L.T. Scott, R.L. Kuczkowski, J. Am. Chem. Soc. 2005, 127(12), 4345-4349, https://doi.org/10.1021/ja0426239.
M. Juriček, N.L. Strutt, J.C. Barnes, A.M. Butterfield, E.J. Dale, K.K Baldridge, J.F. Stoddart, J.S. Siegel, Nat. Chem. 2014, 6, 222-228, https://doi.org/10.1038/nchem.1842.
A. Hosseini, S. Taylor, G. Accorsi, N. Armaroli, C.A. Reed, P.D.W. Boyd, J. Am. Chem. Soc. 2006, 128(49), 15903-15913, https://doi.org/10.1021/ja066031x.
D. Canevet, M. Gallego, H. Isla, A. de Juan, E.M. Perez, N. Martin, J. Am. Chem. Soc. 2011, 133(9), 3184-3190, https://doi.org/10.1021/ja111072j.
L.N. Dawe, T.A. AlHujran, H.-A. Tran, J.I. Mercer, E.A. Jackson, L.T. Scott, P.E. Georghiou, Chem. Commun. 2012, 48, 5563-5565, https://doi.org/10.1039/C2CC30652B.
S. Mizyed, P.E. Georghiou, M. Bancu, B. Cuadra, A.K. Rai, P. Cheng, L.T. Scott, J. Am. Chem. Soc. 2001, 123(51), 12770-12774, https://doi.org/10.1021/ja016761z.
P.E. Georghiou, A.H. Tran, S. Mizyed, M. Bancu, L.T.J. Scott, J. Org. Chem. 2005, 70(16), 6158-6163, https://doi.org/10.1021/jo0503761.
J. Stanojkovic, N. Terenti, M.C. Stuparu, JACS Au 2025, 5(4), 1707-1716, https://doi.org/10.1021/jacsau.4c01218.
A. Sygula, F.R. Fronczek, R. Sygula, P.W. Rabideau, M.M. Olmstead, J. Am. Chem. Soc. 2007, 129(13), 3842-3843, https://doi.org/10.1021/ja070616p.
A. Sygula, Synlett 2016, 27(14), 2070-2080, https://doi.org/10.1055/s-0035-1562469.
M. Yanney, F.R. Fronczek, A. Sygula, Angew. Chem., Int. Ed. 2015, 54(38), 11153-11156, https://doi.org/10.1002/anie.201505327.
P. L. Abeyratne Kuragama, F.R. Fronczek, A. Sygula, Org. Lett. 2015, 17(21), 5292-5295, https://doi.org/10.1021/acs.orglett.5b02666.
C.M. Alvarez, G. Aullon, H. Barbero, L.A. Garcia-Escudero, C. Martinez-Perez, J.M. Martin-Alvarez, D. Miguel, Org. Lett. 2015, 17(11), 2578-2581, https://doi.org/10.1021/acs.orglett.5b01161.
D.-C. Yang, M. Li, C.-F. Chen, Chem. Commun. 2017, 53, 9336-9339, https://doi.org/10.1039/C7CC03519E.
D. Halilovic, V. Rajeshkumar, M.C. Stuparu, Org. Lett. 2021, 23(4), 1468-1472, https://doi.org/10.1021/acs.orglett.1c00146.
A. Sacristan-Martin, D. Miguel, A. Diez-Varga, H. Barbero, C.M. Alvarez, J. Org. Chem. 2022, 87(24), 16691-16706, https://doi.org/10.1021/acs.joc.2c02345.
C.M. Alvarez, L.A. Garcia-Escudero, R. Garcia-Rodriguez, J.M. Martin-Alvarez, D. Miguel, V. M. Rayon, Dalton Trans. 2014, 43, 15693–15696, https://doi.org/10.1039/C4DT02078B.
S. Ibanez, C. Mejuto, K. Ceron, P.J. Sanz-Miguel, E. Peris, Chem. Sci. 2024, 15, 13415-13420, https://doi.org/10.1039/D4SC03661A.
H. Barbero, S. Ferrero, L. Alvarez-Miguel, P. Gomez-Iglesias, D. Miguel, C.M. Alvarez, Chem. Commun. 2016, 52, 12964-12967, https://doi.org/10.1039/C6CC06445K.
A. Sacristan-Martin, H. Barbero, S. Ferrero, D. Miguel, R. Garcia-Rodriguez, C.M. Alvarez, Chem. Commun. 2021, 57, 11013-11016, https://doi.org/10.1039/D1CC03451K.
A. Sacristan-Martin, D. Miguel, H. Barbero, C.M. Alvarez, Org. Lett. 2022, 24(32), 5879-5883, https://doi.org/10.1021/acs.orglett.2c01856.
M. Yanney, A. Sygula, Tetrahedron Lett. 2013, 54(21), 2604-2607, https://doi.org/10.1016/j.tetlet.2013.03.009.
C.M. Alvarez, H. Barbero, S. Ferrero, D.J. Miguel, Org. Chem. 2016, 81(14), 6081-6086, https://doi.org/10.1021/acs.joc.6b00454.
A. Sacristan-Martin, N. Alvarez-Llorente, A. Diez-Varga, H. Barbero, C.M. Alvarez, Inorg. Chem. 2025, 64(5), 2360-2370, https://doi.org/10.1021/acs.inorgchem.4c04608.
S. Ferrero, H. Barbero, D. Miguel, R. Garcia-Rodriguez, C.M. Alvarez, J. Org. Chem. 2020, 85(7), 4918-4926, https://doi.org/10.1021/acs.joc.0c00072.
N. Alvarez-Llorente, A. J. Stasyuk, A. Diez-Varga, S. Ferrero, M. Sola, H. Barbero, C.M. Alvarez, Org. Lett. 2025, 27(1), 357-362, https://doi.org/10.1021/acs.orglett.4c04385.
M.C. Stuparu, Angew. Chem., Int. Ed. 2013, 52(30), 7786-7790, https://doi.org/10.1002/anie.201303032.
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