Interplay between a Foldamer Helix and a Macrocycle in a Foldarotaxane Architecture.
crystallography
foldamers
molecular motion
rotaxanes
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
06 04 2021
06 04 2021
Historique:
received:
08
01
2021
pubmed:
22
1
2021
medline:
22
1
2021
entrez:
21
1
2021
Statut:
ppublish
Résumé
The design and synthesis of a novel rotaxane/foldaxane hybrid architecture is reported. The winding of an aromatic oligoamide helix host around a dumbbell-shaped thread-like guest, or axle, already surrounded by a macrocycle was evidenced by NMR spectroscopy and X-ray crystallography. The process proved to depend on the position of the macrocycle along the axle and the associated steric hindrance. The macrocycle thus behaves as a switchable shield that modulates the affinity of the helix for the axle. Reciprocally, the foldamer helix acts as a supramolecular auxiliary that compartmentalizes the axle. In some cases, the macrocycle is forced to move along the axle to allow the foldamer to reach its best recognition site.
Identifiants
pubmed: 33475210
doi: 10.1002/anie.202100349
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
8380-8384Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
C. J. Bruns, J. F. Stoddart, The nature of the mechanical bond: From Molecules to Machines, Wiley, Hoboken, 2016.
E. A. Neal, S. M. Goldup, Chem. Commun. 2014, 50, 5128-5142;
P. Waelès, M. Gauthier, F. Coutrot, Angew. Chem. Int. Ed. 2021, https://doi.org/10.1002/anie.202007496;
Angew. Chem. 2021, https://doi.org/10.1002/ange.202007496;
J. Gassensmith, J. M. Baumes, B. D. Smith, Chem. Commun. 2009, 6329-6338;
M. J. Frampton, H. L. Anderson, Angew. Chem. Int. Ed. 2007, 46, 1028-1064;
Angew. Chem. 2007, 119, 1046-1083;
A. Martinez-Cuezva, C. Lopez-Leonardo, M. Alajarin, J. Berna, Synlett 2019, 30, 893-902;
F. Modicom, E. M. G. Jamieson, E. Rochette, S. M. Goldup, Angew. Chem. Int. Ed. 2019, 58, 3875-3879;
Angew. Chem. 2019, 131, 3915-3919.
H. Tian, Q.-C. Wang, Chem. Soc. Rev. 2006, 35, 361-374;
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;
F. Coutrot, ChemistryOpen 2015, 4, 556-576;
H.-Y. Zhou, Y. Han, C.-F. Chen, Mater. Chem. Front. 2020, 4, 12-28;
S. Kassem, T. van Leeuwen, A. S. Lubbe, M. R. Wilson, B. L. Feringa, D. A. Leigh, Chem. Soc. Rev. 2017, 46, 2592-2621;
E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. Int. Ed. 2007, 46, 72-191;
Angew. Chem. 2007, 119, 72-196.
D. A. Leigh, M. A. F. Morales, E. M. Pérez, J. K. Y. Wong, C. G. Saiz, A. M. Z. Slawin, A. J. Carmichael, D. M. Haddleton, A. M. Brouwer, W. J. Buma, G. W. H. Wurpel, S. León, F. Zerbetto, Angew. Chem. Int. Ed. 2005, 44, 3062-3067;
Angew. Chem. 2005, 117, 3122-3127;
C. Romuald, A. Ardá, C. Clavel, J. Jiménez-Barbero, F. Coutrot, Chem. Sci. 2012, 3, 1851-1857;
H. Tian, R. Li, P.-H. Lin, K. Meguellati, New J. Chem. 2020, 44, 10628.
E. Busseron, C. Romuald, F. Coutrot, Chem. Eur. J. 2010, 16, 10062-10073;
D. Inamori, H. Masai, T. Tamaki, J. Terao, Chem. Eur. J. 2020, 26, 3385-3389.
A. Altieri, G. Bottari, F. Dehez, D. A. Leigh, J. K. Y. Wong, F. Zerbetto, Angew. Chem. Int. Ed. 2003, 42, 2296-2300;
Angew. Chem. 2003, 115, 2398-2402;
J. J. Yu, L. Y. Zhao, Z. T. Shi, Q. Zhang, G. London, W. J. Liang, C. Gao, M. M. Li, X. M. Cao, H. Tian, B. L. Feringa, D. H. Qu, J. Org. Chem. 2019, 84, 5790-5802.
A. Martinez-Cuezva, J. Berna, R.-A. Orenes, A. Pastor, M. Alajarin, Angew. Chem. Int. Ed. 2014, 53, 6762-6767;
Angew. Chem. 2014, 126, 6880-6885.
Y. Ferrand, I. Huc, Acc. Chem. Res. 2018, 51, 970-977.
Q. Gan, Y. Ferrand, C. Bao, B. Kauffmann, A. Grélard, H. Jiang, I. Huc, Science 2011, 331, 1172-1175;
Y. Ferrand, Q. Gan, B. Kauffmann, H. Jiang, I. Huc, Angew. Chem. Int. Ed. 2011, 50, 7572-7575;
Angew. Chem. 2011, 123, 7714-7717;
S. A. Denisov, Q. Gan, X. Wang, L. Scarpantonio, Y. Ferrand, B. Kauffmann, G. Jonusauskas, I. Huc, N. D. McClenaghan, Angew. Chem. Int. Ed. 2016, 55, 1328-1333;
Angew. Chem. 2016, 128, 1350-1355;
Q. Gan, X. Wang, B. Kauffmann, F. Rosu, Y. Ferrand, I. Huc, Nat. Nanotechnol. 2017, 12, 447-454.
X. Wang, B. Wicher, Y. Ferrand, I. Huc, J. Am. Chem. Soc. 2017, 139, 9350-9358.
We define here a foldarotaxane as the combination of a foldaxane and a rotaxane around the same axle. Foldamers and rotaxanes have previously been combined in other ways, for example when a foldamer is an integral part of the axle of a rotaxane, see for example:
K.-D. Zhang, X. Zhao, G.-T. Wang, Y. Liu, Y. Zhang, H.-J. Lu, X.-K. Jiang, Z.-T. Li, Angew. Chem. Int. Ed. 2011, 50, 9866-9870;
Angew. Chem. 2011, 123, 10040-10044;
W.-K. Wang, Z.-Y. Xu, Y.-C. Zhang, H. Wang, D.-W. Zhang, Y. Liu, Z.-T. Li, Chem. Commun. 2016, 52, 7490-7493;
D. A. Leigh, L. Pirvu, F. Schaufelberger, D. J. Tetlow, L. Zhang, Angew. Chem. Int. Ed. 2018, 57, 10484-10488;
Angew. Chem. 2018, 130, 10644-10648;
A. Moretto, I. Menegazzo, M. Crisma, E. J. Shotton, H. Nowell, S. Mammi, C. Toniolo, Angew. Chem. Int. Ed. 2009, 48, 8986-8989;
Angew. Chem. 2009, 121, 9148-9151.
For background on the concept of compartmentalization, see
J. S. Hannam, S. M. Lacy, D. A. Leigh, C. G. Saiz, A. M. Z. Slawin, S. G. Stitchell, Angew. Chem. Int. Ed. 2004, 43, 3260-3264;
Angew. Chem. 2004, 116, 3322-3326;
M. N. Chatterjee, E. R. Kay, D. A. Leigh, J. Am. Chem. Soc. 2006, 128, 4058-4073;
V. Serreli, C.-F. Lee, E. R. Kay, D. A. Leigh, Nature 2007, 445, 523-527;
E. R. Kay, D. A. Leigh, Pure Appl. Chem. 2008, 80, 17-29;
M. Alvarez-Pérez, S. M. Goldup, D. A. Leigh, A. M. Z. Slawin, J. Am. Chem. Soc. 2008, 130, 1836-1838;
A. Carlone, S. M. Goldup, N. Lebrasseur, D. A. Leigh, A. Wilson, J. Am. Chem. Soc. 2012, 134, 8321-8323;
E. Busseron, F. Coutrot, J. Org. Chem. 2013, 78, 4099-4106;
W.-K. Wang, Z.-Y. Xu, Y.-C. Zhang, H. Wang, D.-W. Zhang, Y. Liu, Z.-T. Li, Chem. Commun. 2016, 52, 7490-7493;
Y. Mochizuki, K. Ikeyatsu, Y. Mutoh, S. Hosoya, S. Saito, Org. Lett. 2017, 19, 4347-4350.
A. G. Kolchinski, D. H. Busch, N. W. Alcock, J. Chem. Soc. Chem. Commun. 1995, 1289-1291.
B. Riss-Yaw, J. Morin, C. Clavel, F. Coutrot, Molecules 2017, 22, 2017.
T. Legigan, B. Riss-Yaw, C. Clavel, F. Coutrot, Chem. Eur. J. 2016, 22, 8835-8847;
B. Riss-Yaw, T. X. Métro, F. Lamaty, F. Coutrot, RSC Adv. 2019, 9, 21587-21590.
This was achieved in the presence of Et3N (3 equiv.) to prevent any adverse acidity from CDCl3 decomposition, which may cause the protonation of the pyridyl units of the helix, hence its unfolding. Note that this amount of Et3N does not deprotonate the ammonium moiety of the [2]rotaxane which is stabilized upon interacting with DB24C8. For a reference, see: N. Kihara, Y. Tachibana, H. Kawasaki, T. Takata, Chem. Lett. 2000, 29, 506-507.
For other examples related to the protection of functionalities on a thread by a macrocycle, see:
T. Oku, Y. Furusho, T. Takata, Org. Lett. 2003, 5, 4923-4925;
A. H. Parham, B. Windisch, F. Vögtle, Eur. J. Org. Chem. 1999, 1233-1238;
D. A. Leigh, E. M. Pérez, Chem. Commun. 2004, 2262-2263;
A. Mateo-Alonso, P. Brough, M. Prato, Chem. Commun. 2007, 1412-1414;
F. Scarel, G. Valenti, S. Gaikwad, M. Marcaccio, F. Paolucci, A. Mateo-Alonso, Chem. Eur. J. 2012, 18, 14063-14068;
D. M. D'Souza, D. A. Leigh, L. Mottier, K. M. Mullen, F. Paolucci, S. J. Teat, S. Zhang, J. Am. Chem. Soc. 2010, 132, 9465-9470;
M. Gauthier, F. Coutrot, Eur. J. Org. Chem. 2019, 21, 3391-3395;
M. Franz, J. A. Januszewski, D. Wendinger, C. Neiss, L. D. Movsisyan, F. Hampel, H. L. Anderson, A. Görling, R. R. Tykwinski, Angew. Chem. Int. Ed. 2015, 54, 6645-6649;
Angew. Chem. 2015, 127, 6746-6750;
A. Fernandes, A. Viterisi, F. Coutrot, S. Potok, D. A. Leigh, V. Aucagne, S. Papot, Angew. Chem. Int. Ed. 2009, 48, 6443-6447;
Angew. Chem. 2009, 121, 6565-6569;
N. Kihara, S. Motoda, T. Yokozawa, T. Takata, Org. Lett. 2005, 7, 1199-1202.
Similarly, it has been shown that the reactivity of a function, when in interaction with an encircling DB24C8, may depend on the proximity of another site of recognition, see:
G. Ragazzona, C. Schäfera, P. Franchia, S. Silvia, B. Colasson, M. Lucarini, A. Credi, Proc. Natl. Acad. Sci. USA 2018, 115, 9385-9390;
C. Romuald, E. Busseron, F. Coutrot, J. Org. Chem. 2010, 75, 6516-6531;
G. Ragazzon, A. Credi, B. Colasson, Chem. Eur. J. 2017, 23, 2149-2156.
In order to make a comparison, the association constant in chloroform at 293 K between a similar dialkylammonium and the DB24C8 is about 500 M−1. It is much lower with amide and even lower with carbamate.