The Diversity of Cucurbituril Molecular Switches and Shuttles.

cucurbituril host:guest macrocycle shuttle switch

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
14 Dec 2023
Historique:
received: 03 07 2023
pubmed: 19 9 2023
medline: 19 9 2023
entrez: 19 9 2023
Statut: ppublish

Résumé

Ring translocation switches and shuttles featuring a macrocycle (or a ring molecule) navigating between two or more stations continue to attract attention. While the vast majority of these systems are developed in organic solvents, the cucurbituril (CB) macrocycles are ideally suited to prepare such systems in water. Indeed, their stability and their relatively high affinity for relevant guest molecules are key attributes toward translating the progresses made in organic solvents, into water. This concept article summarizes the findings, key advances and multiple possibilities offered by CBs toward advanced molecular switches and shuttles in water.

Identifiants

pubmed: 37725407
doi: 10.1002/chem.202302114
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202302114

Subventions

Organisme : Aix-Marseille Université
Organisme : Centre National de la Recherche Scientifique
Organisme : France 2030 investment plan
ID : AMX-20-IET-015

Informations de copyright

© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Références

 
J. B. Rafferty, S. E. Sedelnikova, D. Hargreaves, P. J. Artymiuk, P. J. Baker, G. J. Sharples, A. A. Mahdi, R. G. Lloyd, D. W. Rice, Science 1996, 274, 415-421;
N. D. Thomsen, M. R. Lawson, L. B. Witkowsky, S. Qu, J. M. Berger, Proc. Natl. Acad. Sci. USA 2016, 113, E7691-E7700;
H. F. Noller, L. Lancaster, J. Zhou, S. Mohan, Nat. Struct. Mol. Biol. 2017, 24, 1021-1027.
L. Zhou, L. A. Sazanov, Science 2019, 365, eaaw9144.
 
H. Noji, R. Yasuda, M. Yoshida, K. Kinosita Jr., Nature 1997, 386, 299-302;
A. Hahn, J. Vonck, D. J. Mills, T. Meier, W. Kühlbrandt, Science 2018, 360, eaat4318.
 
N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 1999, 401, 152-155;
S. Erbas-Cakmak, S. D. P. Fielden, U. Karaca, D. A. Leigh, C. T. McTernan, D. J. Tetlow, M. R. Wilson, Science 2017, 358, 340-343;
A. W. Heard, S. M. Goldup, ACS Cent. Sci. 2020, 6, 117-128;
S. Borsley, E. Kreidt, D. A. Leigh, B. M. W. Roberts, Nature 2022, 604, 80-85.
S. S. Patel, K. M. Picha, Annu. Rev. Biochem. 2000, 69, 651-697.
T. M. Lohman, K. P. Bjornson, Annu. Rev. Biochem. 1996, 65, 169-214.
A. M. Pyle, Annu. Rev. Biochem. 2008, 37, 317-336.
 
V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Res. 2001, 34, 433-444;
S. Silvi, M. Venturi, A. Credi, J. Mater. Chem. 2009, 19, 2279-2294;
S. Erbas-Cakmak, D. A. Leigh, C. T. McTernan, A. L. Nussbaumer, Chem. Rev. 2015, 115, 10081-10206;
S. Kassem, T. van Leeuwen, A. S. Lubbe, M. R. Wilson, B. L. Feringa, D. A. Leigh, Chem. Soc. Rev. 2017, 46, 2592-2621;
I. Aprahamian, ACS Cent. Sci. 2020, 6, 347-358.
P. L. Anelli, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1991, 113, 5131-5133.
R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137.
A. Blanco-Gómez, P. Cortón, L. Barravecchia, I. Neira, E. Pazos, C. Peinador, M. D. García, Chem. Soc. Rev. 2020, 49, 3834-3862.
 
J. D. Crowley, S. M. Goldup, A.-L. Lee, D. A. Leigh, R. T. McBurney, Chem. Soc. Rev. 2009, 38, 1530-1541;
C. J. Bruns, J. F. Stoddart, Acc. Chem. Res. 2014, 47, 2186-2199;
M. Xue, Y. Yang, X. Chi, X. Yan, F. Huang, Chem. Rev. 2015, 115, 7398-7501;
J. F. Stoddart, Angew. Chem. Int. Ed. 2017, 56, 11094-11125;
J.-P. Sauvage, Angew. Chem. Int. Ed. 2017, 56, 11080-11093.
Q. Gan, Y. Ferrand, C. Bao, B. Kauffmann, A. Grélard, H. Jiang, I. Huc, Science 2011, 331, 1172-1175.
 
K. Nørgaard, B. W. Laursen, S. Nygaard, K. Kjaer, H.-R. Tseng, A. H. Flood, J. F. Stoddart, T. Bjørnholm, Angew. Chem. Int. Ed. 2005, 44, 7035-7039;
M. Hmadeh, A. C. Fahrenbach, S. Basu, A. Trabolsi, D. Benitez, H. Li, A.-M. Albrecht-Gary, M. Elhabiri, J. F. Stoddart, Chem. Eur. J. 2011, 17, 6076-6087;
H. Li, A. C. Fahrenbach, A. Coskun, Z.-X. Zhu, G. Barin, Y.-L. Zhao, Y. Y. Botros, J.-P. Sauvage, J. F. Stoddart, Angew. Chem. Int. Ed. 2011, 50, 6782;
L. Fang, S. Basu, C.-H. Sue, A. C. Fahrenbach, J. F. Stoddart, J. Am. Chem. Soc. 2011, 133, 396-399;
C. J. Bruns, Symmetry 2019, 11, 1249.
 
M. R. Panman, B. H. Bakker, D. den Uyl, E. R. Kay, D. A. Leigh, W. J. Buma, A. M. Brouwer, J. A. J. Geenevasen, S. Woutersen, Nat. Chem. 2013, 5, 929-934;
Z. Wu, S. Wang, Z. Zhang, Y. Zhang, Y. Yin, H. Shi, S. Jiao, RSC Adv. 2022, 12, 30495-30500.
 
Q.-C. Wang, D.-H. Qu, J. Ren, K. Chen, H. Tian, Angew. Chem. Int. Ed. 2004, 43, 2661-2665;
H. Murakami, A. Kawabuchi, R. Matsumoto, T. Ido, N. Nakashima, J. Am. Chem. Soc. 2005, 127, 15891-15899.
 
A. Harada, Acc. Chem. Res. 2001, 34, 456-464;
C. A. Stanier, S. J. Alderman, T. D. W. Claridge, H. L. Anderson, Angew. Chem. Int. Ed. 2002, 41, 1769-1772;
X. Ma, H. Tian, Chem. Soc. Rev. 2010, 39, 70-80;
T. Girek, J. Inclusion Phenom. Macrocyclic Chem. 2012, 74, 1-21;
D.-H. Qu, Q.-C. Wang, Q.-W. Zhang, X. Ma, H. Tian, Chem. Rev. 2015, 115, 7543-7588;
A. Hashidzume, H. Yamaguchi, A. Harada, Eur. J. Org. Chem. 2019, 2019, 3344-3357;
E. Liu, S. Cherraben, L. Boulo, C. Troufflard, B. Hasenknopf, G. Vives, M. Sollogoub, Chem 2023, 9, 1147-1163.
S. J. Barrow, S. Kasera, M. J. Rowland, J. del Barrio, O. A. Scherman, Chem. Rev. 2015, 115, 12320-12406.
W. L. Mock, J. Pierpont, J. Chem. Soc. Chem. Commun. 1990, 1509-1511.
J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2000, 122, 540-541.
 
S. Liu, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 16798-16799;
E. Pazos, P. Novo, C. Peinador, A. E. Kaifer, M. D. García, Angew. Chem. Int. Ed. 2019, 58, 403-416;
X. Hu, F. Liu, X. Zhang, Z. Zhao, S. Liu, Chem. Sci. 2020, 11, 4779-4785;
C. Li, A.-D. Manick, Y. Zhao, F. Liu, B. Chatelet, R. Rosas, D. Siri, D. Gigmes, V. Monnier, L. Charles, J. Broggi, S. Liu, A. Martinez, A. Kermagoret, D. Bardelang, Chem. Eur. J. 2022, e202201656.
 
V. Serreli, C.-F. Lee, E. R. Kay, D. A. Leigh, Nature 2007, 445, 523-527;
J. M. Abendroth, O. S. Bushuyev, P. S. Weiss, C. J. Barrett, ACS Nano 2015, 9, 7746-7768;
Y. Ren, R. Jamagne, D. J. Tetlow, D. A. Leigh, Nature 2022, 612, 78-82.
L. Zhu, M. Zhu, Y. Zhao, ChemPlusChem 2017, 82, 30-41.
A. Coskun, D. C. Friedman, H. Li, K. Patel, H. A. Khatib, J. F. Stoddart, J. Am. Chem. Soc. 2009, 131, 2493-2495.
F. Biedermann, V. D. Uzunova, O. A. Scherman, W. M. Nau, A. De Simone, J. Am. Chem. Soc. 2012, 134, 15318-15323.
 
X. Hou, C. Ke, J. Fraser Stoddart, Chem. Soc. Rev. 2016, 45, 3766-3780;
F. d'Orchymont, J. P. Holland, J. Am. Chem. Soc. 2023, 145, 12894-12910.
K. Moon, A. E. Kaifer, Org. Lett. 2004, 6, 185-188.
M. Freitag, L. Gundlach, P. Piotrowiak, E. Galoppini, J. Am. Chem. Soc. 2012, 134, 3358-3366.
F. Benyettou, K. Nchimi-Nono, M. Jouiad, Y. Lalatonne, I. Milosevic, L. Motte, J.-C. Olsen, N. I. Saleh, A. Trabolsi, Chem. Eur. J. 2015, 21, 4607-4613.
 
W. Ong, M. Gómez-Kaifer, A. E. Kaifer, Org. Lett. 2002, 4, 1791-1794;
H.-J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA 2002, 99, 5007-5011;
P. Dalvand, K. Nchimi Nono, D. Shetty, F. Benyettou, Z. Asfari, C. Platas-Iglesias, M. A. Olson, A. Trabolsi, M. Elhabiri, RSC Adv. 2021, 11, 29543-29554.
Z. Huang, L. Yang, Y. Liu, Z. Wang, O. A. Scherman, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 5351-5355.
F. Liu, H. Karoui, A. Rockenbauer, S. Liu, O. Ouari, D. Bardelang, Molecules 2020, 25, 776.
S. Schoder, H. V. Schröder, L. Cera, R. Puttreddy, A. Güttler, U. Resch-Genger, K. Rissanen, C. A. Schalley, Chem. Eur. J. 2019, 25, 3257-3261.
V. Kolman, M. S. A. Khan, M. Babinsky, R. Marek, V. Sindelar, Org. Lett. 2011, 13, 6148-6151.
X.-L. Ni, J.-M. Yi, S. Song, Y.-Q. Zhang, S.-F. Xue, Q.-J. Zhu, Z. Tao, Tetrahedron 2013, 69, 6219-6222.
L. Zhu, H. Yan, X.-J. Wang, Y. Zhao, J. Org. Chem. 2012, 77, 10168-10175.
W. Lei, Q. Zhou, G. Jiang, Y. Hou, B. Zhang, X. Cheng, X. Wang, ChemPhysChem 2011, 12, 2933-2940.
X. Y. Deng, W. T. Xu, M. Liu, M. X. Yang, Q. J. Zhu, B. Lü, Z. Tao, Supramol. Chem. 2019, 31, 616-624.
W. Zhang, Y. Luo, Y. Zhou, M. Liu, W. Xu, B. Bian, Z. Tao, X. Xiao, Dyes Pigm. 2020, 176, 108235.
J. Wook Lee, K. Kim, K. Kim, Chem. Commun. 2001, 1042-1043.
D. Tuncel, M. Katterle, Chem. Eur. J. 2008, 14, 4110-4116.
X. Ling, E. L. Samuel, D. L. Patchell, E. Masson, Org. Lett. 2010, 12, 2730-2733.
E. Y. Chernikova, S. V. Tkachenko, O. A. Fedorova, A. S. Peregudov, I. A. Godovikov, N. E. Shepel, S. Minkovska, A. Kurutos, N. Gadjev, T. G. Deligeorgiev, Y. V. Fedorov, Dyes Pigm. 2016, 131, 206-214.
V. Sindelar, S. Silvi, A. E. Kaifer, Chem. Commun. 2006, 2185-2187.
H. Shi, K. Zhang, R.-L. Lin, W.-Q. Sun, X.-F. Chu, X.-H. Liu, J.-X. Liu, Asian J. Org. Chem. 2019, 8, 339-343.
V. Sindelar, K. Moon, A. E. Kaifer, Org. Lett. 2004, 6, 2665-2668.
X. Yang, Q. Cheng, V. Monnier, L. Charles, H. Karoui, O. Ouari, D. Gigmes, R. Wang, A. Kermagoret, D. Bardelang, Angew. Chem. Int. Ed. 2021, 60, 6617-6623.
W. Wu, S. Song, X. Cui, T. Sun, J.-X. Zhang, X.-L. Ni, Chin. Chem. Lett. 2018, 29, 95-98.
X. Zhang, X. Shi, S. Su, G. Zhou, X.-L. Ni, Dyes Pigm. 2020, 172, 107785.
Y. Gong, H. Chen, X. Ma, H. Tian, ChemPhysChem 2016, 17, 1934-1938.
A. M. Diniz, N. Basílio, H. Cruz, F. Pina, A. J. Parola, Faraday Discuss. 2015, 185, 361-379.
L. Mikulu, R. Michalicova, V. Iglesias, M. A. Yawer, A. E. Kaifer, P. Lubal, V. Sindelar, Chem. Eur. J. 2017, 23, 2350-2355.
A. Seco, S. Yu, A. Tron, N. D. McClenaghan, F. Pina, A. Jorge Parola, N. Basílio, Chem. Eur. J. 2021, 27, 16512-16522.
M. Baroncini, C. Gao, V. Carboni, A. Credi, E. Previtera, M. Semeraro, M. Venturi, S. Silvi, Chem. Eur. J. 2014, 20, 10737-10744.
N. Rad, V. Sashuk, Chem. Sci. 2022, 13, 12440-12444.
S. Liu, C. Ruspic, P. Mukhopadhyay, S. Chakrabarti, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 15959-15967.
D. Sobransingh, A. E. Kaifer, Org. Lett. 2006, 8, 3247-3250.
W. S. Jeon, H.-J. Kim, C. Lee, K. Kim, Chem. Commun. 2002, 1828-1829.
W. S. Jeon, A. Y. Ziganshina, J. W. Lee, Y. H. Ko, J.-K. Kang, C. Lee, K. Kim, Angew. Chem. Int. Ed. 2003, 42, 4097-4100.
I. Neira, O. Domarco, J. L. Barriada, P. Franchi, M. Lucarini, M. D. García, C. Peinador, Org. Biomol. Chem. 2020, 18, 5228-5233.
X. Yang, R. Wang, A. Kermagoret, D. Bardelang, Angew. Chem. Int. Ed. 2020, 59, 21280-21292.
L. Cera, C. A. Schalley, Chem. Sci. 2014, 5, 2560-2567.
N. Noujeim, B. Jouvelet, A. R. Schmitzer, J. Phys. Chem. B 2009, 113, 16159-16168.
I. W. Wyman, D. H. Macartney, Org. Biomol. Chem. 2009, 7, 4045-4051.
I. W. Wyman, D. H. Macartney, J. Org. Chem. 2009, 74, 8031-8038.
M. Pessêgo, J. P. Da Silva, J. A. Moreira, L. García-Río, ChemPlusChem 2013, 78, 1058-1064.
Y. Song, X. Huang, H. Hua, Q. Wang, Dyes Pigm. 2017, 137, 229-235.
E. Babjaková, P. Branná, M. Kuczyńska, M. Rouchal, Z. Prucková, L. Dastychová, J. Vícha, R. Vícha, RSC Adv. 2016, 6, 105146-105153.
S. Andersson, D. Zou, R. Zhang, S. Sun, L. Sun, Org. Biomol. Chem. 2009, 7, 3605-3609.
M. R. Geraskina, A. S. Dutton, M. J. Juetten, S. A. Wood, A. H. Winter, Angew. Chem. Int. Ed. 2017, 56, 9435-9439.
A. Y. Ruleva, Y. V. Fedorov, T. M. Aliev, V. V. Novikov, N. E. Shepel, M. A. Ustimova, O. A. Fedorova, J. Incl. Phenom. Macrocycl. 2020, 98, 249-259.
Y. Liu, X.-Y. Li, H.-Y. Zhang, C.-J. Li, F. Ding, J. Org. Chem. 2007, 72, 3640-3645.
P. Branná, J. Černochová, M. Rouchal, P. Kulhánek, M. Babinský, R. Marek, M. Nečas, I. Kuřitka, R. Vícha, J. Org. Chem. 2016, 81, 9595-9604.
S. S. Thomas, H. Tang, C. Bohne, J. Am. Chem. Soc. 2019, 141, 9645-9654.
 
Q. Cheng, H. Yin, R. Rosas, D. Gigmes, O. Ouari, R. Wang, A. Kermagoret, D. Bardelang, Chem. Commun. 2018, 54, 13825-13828;
H. Yin, R. Rosas, D. Gigmes, O. Ouari, R. Wang, A. Kermagoret, D. Bardelang, Org. Lett. 2018, 20, 3187-3191.
A. Kriat, S. Pascal, B. Kauffmann, Y. Ferrand, D. Bergé-Lefranc, D. Gigmes, O. Siri, A. Kermagoret, D. Bardelang, Chem. Eur. J. 2023, e202300633.
R.-L. Lin, R. Li, H. Shi, K. Zhang, D. Meng, W.-Q. Sun, K. Chen, J.-X. Liu, J. Org. Chem. 2020, 85, 3568-3575.
E. Y. Chernikova, D. V. Berdnikova, Y. V. Fedorov, O. A. Fedorova, F. Maurel, G. Jonusauskas, Phys. Chem. Chem. Phys. 2017, 19, 25834-25839.
S. Angelos, N. M. Khashab, Y.-W. Yang, A. Trabolsi, H. A. Khatib, J. F. Stoddart, J. I. Zink, J. Am. Chem. Soc. 2009, 131, 12912-12914.
S. Choi, R. D. Mukhopadhyay, Y. Kim, I.-C. Hwang, W. Hwang, S. K. Ghosh, K. Baek, K. Kim, Angew. Chem. Int. Ed. 2019, 58, 16850-16853.
N. K. Petrov, D. A. Ivanov, M. V. Alfimov, ACS Omega 2019, 4, 11500-11507.
E. Y. Chernikova, A. I. Grachev, A. S. Peregudov, O. A. Fedorova, Y. V. Fedorov, Dyes Pigm. 2021, 189, 109194.
 
C. P. Collier, G. Matterstei, E. W. Wong, Y. Luo, K. Beverly, J. Sampaio, F. M. Raymo, J. F. Stoddart, J. R. Heath, Science 2000, 289, 1172-1175;
C. Cheng, P. R. McGonigal, S. T. Schneebeli, H. Li, N. A. Vermeulen, C. Ke, J. F. Stoddart, Nat. Nanotechnol. 2015, 10, 547-553;
Y. Qiu, B. Song, C. Pezzato, D. Shen, W. Liu, L. Zhang, Y. Feng, Q.-H. Guo, K. Cai, W. Li, H. Chen, M. T. Nguyen, Y. Shi, C. Cheng, R. D. Astumian, X. Li, J. F. Stoddart, Science 2020, 368, 1247-1253;
L. Zhang, Y. Qiu, W.-G. Liu, H. Chen, D. Shen, B. Song, K. Cai, H. Wu, Y. Jiao, Y. Feng, J. S. W. Seale, C. Pezzato, J. Tian, Y. Tan, X.-Y. Chen, Q.-H. Guo, C. L. Stern, D. Philp, R. D. Astumian, W. A. Goddard, J. F. Stoddart, Nature 2023, 613, 280-286.
 
A. Goujon, T. Lang, G. Mariani, E. Moulin, G. Fuks, J. Raya, E. Buhler, N. Giuseppone, J. Am. Chem. Soc. 2017, 139, 14825-14828;
T. Muramatsu, S. Shimizu, J. M. Clough, C. Weder, Y. Sagara, ACS Appl. Mater. Interfaces 2023, 15, 8502-8509.
D. Dattler, G. Fuks, J. Heiser, E. Moulin, A. Perrot, X. Yao, N. Giuseppone, Chem. Rev. 2020, 120, 310-433.
Q. Li, G. Fuks, E. Moulin, M. Maaloum, M. Rawiso, I. Kulic, J. T. Foy, N. Giuseppone, Nat. Nanotechnol. 2015, 10, 161-165.
A. R. Osborne, T. A. Rapoport, B. van den Berg, Annu. Rev. Cell Dev. Biol. 2005, 21, 529-550.
R. Jones, G. Bragagnolo, R. Arranz, J. Reguera, Nature 2021, 589, 615-619.

Auteurs

Anthony Kermagoret (A)

Aix Marseille Univ, CNRS, CINAM, AMUtech, Marseille, France.

David Bardelang (D)

Aix Marseille Univ, CNRS, ICR, AMUtech, Marseille, France.

Classifications MeSH