Metalla-Assembled Electron-Rich Tweezers: Redox-Controlled Guest Release Through Supramolecular Dimerization.
host-guest systems
molecular tweezers
self-assembly
sulfur heterocycles
supramolecular chemistry
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:
07 Jan 2020
07 Jan 2020
Historique:
received:
19
09
2019
revised:
14
10
2019
pubmed:
2
11
2019
medline:
2
11
2019
entrez:
1
11
2019
Statut:
ppublish
Résumé
Developing methodologies for on-demand control of the release of a molecular guest requires the rational design of stimuli-responsive hosts with functional cavities. While a substantial number of responsive metallacages have already been described, the case of coordination-tweezers has been less explored. Herein, we report the first example of a redox-triggered guest release from a metalla-assembled tweezer. This tweezer incorporates two redox-active panels constructed from the electron-rich 9-(1,3-dithiol-2-ylidene)fluorene unit that are facing each other. It dimerizes spontaneously in solution and the resulting interpenetrated supramolecular structure can dissociate in the presence of an electron-poor planar unit, forming a 1:1 host-guest complex. This complex dissociates upon tweezer oxidation/dimerization, offering an original redox-triggered molecular delivery pathway.
Identifiants
pubmed: 31670452
doi: 10.1002/anie.201912016
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
716-720Subventions
Organisme : Campus France
Organisme : Centre National de la Recherche Scientifique
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
B. Li, T. He, Y. Fan, X. Yuan, H. Qiu, S. Yin, Chem. Commun. 2019, 55, 8036-8059;
T. R. Cook, P. J. Stang, Chem. Rev. 2015, 115, 7001-7045.
A. Casini, B. Woods, M. Wenzel, Inorg. Chem. 2017, 56, 14715-14729.
S. Zarra, D. M. Wood, D. A. Roberts, J. R. Nitschke, Chem. Soc. Rev. 2015, 44, 419-432;
H. Amouri, C. Desmarets, J. Moussa, Chem. Rev. 2012, 112, 2015-2041.
T. Y. Kim, R. A. S. Vasdev, D. Preston, J. D. Crowley, Chem. Eur. J. 2018, 24, 14878-14890.
V. Croué, S. Goeb, M. Sallé, Chem. Commun. 2015, 51, 7275-7289.
S. Bivaud, S. Goeb, V. Croué, P. I. Dron, M. Allain, M. Sallé, J. Am. Chem. Soc. 2013, 135, 10018-10021;
S. Bivaud, J. Y. Balandier, M. Chas, M. Allain, S. Goeb, M. Sallé, J. Am. Chem. Soc. 2012, 134, 11968-11970;
S. Goeb, S. Bivaud, P. I. Dron, J.-Y. Balandier, M. Chas, M. Sallé, Chem. Commun. 2012, 48, 3106-3108.
G. Szalóki, V. Croué, V. Carré, F. Aubriet, O. Alévêque, E. Levillain, M. Allain, J. Arago, E. Orti, S. Goeb, M. Sallé, Angew. Chem. Int. Ed. 2017, 56, 16272-16276;
Angew. Chem. 2017, 129, 16490-16494;
V. Croué, S. Goeb, G. Szalóki, M. Allain, M. Sallé, Angew. Chem. Int. Ed. 2016, 55, 1746-1750;
Angew. Chem. 2016, 128, 1778-1782.
M. Hardouin-Lerouge, P. Hudhomme, M. Sallé, Chem. Soc. Rev. 2011, 40, 30-43;
J. Leblond, A. Petitjean, ChemPhysChem 2011, 12, 1043-1051.
S. Bähring, H. D. Root, J. L. Sessler, J. O. Jeppesen, Org. Biomol. Chem. 2019, 17, 2594-2613;
A. Jana, S. Bähring, M. Ishida, S. Goeb, D. Canevet, M. Sallé, J. O. Jeppesen, J. L. Sessler, Chem. Soc. Rev. 2018, 47, 5614-5645;
J. S. Park, J. L. Sessler, Acc. Chem. Res. 2018, 51, 2400-2410;
A. Jana, M. Ishida, J. S. Park, S. Bähring, J. O. Jeppesen, J. L. Sessler, Chem. Rev. 2017, 117, 2641-2710;
Y. Cotelle, M. Hardouin-Lerouge, S. Legoupy, O. Alévêque, E. Levillain, P. Hudhomme, Beilstein J. Org. Chem. 2015, 11, 1023-1036;
M. Hardouin-Lerouge, Y. Cotelle, S. Legoupy, P. Hudhomme, New J. Chem. 2014, 38, 5341-5348;
M. H. Düker, H. Schäfer, M. Zeller, V. A. Azov, J. Org. Chem. 2013, 78, 4905-4912;
T. Poulsen, K. A. Nielsen, A. D. Bond, J. O. Jeppesen, Org. Lett. 2007, 9, 5485-5488;
K. A. Nielsen, W.-S. Cho, J. O. Jeppesen, V. M. Lynch, J. Becher, J. L. Sessler, J. Am. Chem. Soc. 2004, 126, 16296-16297.
Y. Lu, H.-N. Zhang, G.-X. Jin, Acc. Chem. Res. 2018, 51, 2148-2158;
W. M. Bloch, G. H. Clever, Chem. Commun. 2017, 53, 8506-8516;
S.-L. Huang, T. S. A. Hor, G.-X. Jin, Coord. Chem. Rev. 2017, 333, 1-26;
L. Xu, Y. X. Wang, L. J. Chen, H. B. Yang, Chem. Soc. Rev. 2015, 44, 2148-2167;
J. J. Henkelis, M. J. Hardie, Chem. Commun. 2015, 51, 11929-11943;
M. Han, D. M. Engelhard, G. H. Clever, Chem. Soc. Rev. 2014, 43, 1848-1860;
A. Mishra, S. C. Kang, K.-W. Chi, Eur. J. Inorg. Chem. 2013, 5222-5232;
R. Chakrabarty, P. S. Mukherjee, P. J. Stang, Chem. Rev. 2011, 111, 6810-6918.
S. Krykun, M. Allain, V. Carré, F. Aubriet, Z. Voitenko, S. Goeb, M. Sallé, Inorganics 2018, 6, 44-54.
H. Yan, G. Süss-Fink, A. Neels, H. Stoeckli-Evans, J. Chem. Soc. Dalton Trans. 1997, 4345-4350.
L. Avram, Y. Cohen, Chem. Soc. Rev. 2015, 44, 586-602;
A. Macchioni, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, Chem. Soc. Rev. 2008, 37, 479-489.
N. P. E. Barry, J. Furrer, B. Therrien, Helv. Chim. Acta 2010, 93, 1313-1328.
Y. H. Song, N. Singh, J. Jung, H. Kim, E. H. Kim, H. K. Cheong, Y. Kim, K. W. Chi, Angew. Chem. Int. Ed. 2016, 55, 2007-2011;
Angew. Chem. 2016, 128, 2047-2051.
L. Faour, C. Adam, C. Gautier, S. Goeb, M. Allain, E. Levillain, D. Canevet, M. Sallé, Chem. Commun. 2019, 55, 5743-5746.
F. Aparicio, L. Faour, M. Allain, D. Canevet, M. Sallé, Chem. Commun. 2017, 53, 12028-12031.
D. Canevet, M. Gallego, H. Isla, A. de Juan, E. M. Perez, N. Martin, J. Am. Chem. Soc. 2011, 133, 3184-3190;
G. Bastien, P. I. Dron, M. Vincent, D. Canevet, M. Allain, S. Goeb, M. Sallé, Org. Lett. 2016, 18, 5856-5859.
D. F. Perepichka, I. F. Perepichka, O. Ivasenko, A. J. Moore, M. R. Bryce, L. G. Kuz'mina, A. S. Batsanov, N. I. Sokolov, Chem. Eur. J. 2008, 14, 2757-2770;
S. Amriou, C. Wang, A. S. Batsanov, M. R. Bryce, D. F. Perepichka, E. Ortí, R. Viruela, J. Vidal-Gancedo, C. Rovira, Chem. Eur. J. 2006, 12, 3389-3400.