Macrocycle-Directed Construction of Tetrahedral Anion-π Receptors for Nesting Anions with Complementary Geometry.
anion-pi interactions
cooperative binding
encapsulation
macrocycles
tetrahedral cages
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
17 Oct 2019
17 Oct 2019
Historique:
received:
18
07
2019
revised:
07
08
2019
pubmed:
10
8
2019
medline:
28
11
2019
entrez:
10
8
2019
Statut:
ppublish
Résumé
Manipulation of the emerging anion-π interactions in a highly cooperative manner through sophisticated host design represents a very challenging task. In this work, unprecedented tetrahedral anion-π receptors have been successfully constructed for complementary accommodation of tetrahedral and relevant anions. The synthesis was achieved by a macrocycle-directed approach by using large macrocycle precursors bearing four reactive sites, which enabled a kinetic-favored pathway and afforded the otherwise inaccessible tetrahedral cages in considerable yields. Crystal structure suggested that the tetrahedral cages have an enclosed three-dimensional cavity surrounded by four electron-deficient triazine faces in a tetrahedral array. The complementary accommodation of a series of tetrahedral and relevant anions including BF
Identifiants
pubmed: 31398268
doi: 10.1002/chem.201903272
doi:
Substances chimiques
Anions
0
Borates
0
Cross-Linking Reagents
0
Macrocyclic Compounds
0
Perchlorates
0
Sulfates
0
Triazines
0
fluoroboric acid
H429WZ9FBQ
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13275-13279Subventions
Organisme : National Natural Science Foundation of China
ID : 21772203
Organisme : National Natural Science Foundation of China
ID : 21761132024
Organisme : National Natural Science Foundation of China
ID : 91427301
Organisme : National Natural Science Foundation of China
ID : 21871276
Organisme : National Natural Science Foundation of China
ID : 21521002
Organisme : Chinese Academy of Sciences
ID : QYZDJ-SSW-SLH023
Organisme : U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences and Biosciences
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
For reviews see:
B. P. Hay, V. S. Bryantsev, Chem. Commun. 2008, 2417;
D.-X. Wang, M.-X. Wang, Chimia 2011, 65, 939;
A. Frontera, P. Gamez, M. Mascal, T. J. Mooibroek, J. Reedijk, Angew. Chem. Int. Ed. 2011, 50, 9564;
Angew. Chem. 2011, 123, 9736;
H. T. Chifotides, K. R. Dunbar, Acc. Chem. Res. 2013, 46, 894;
P. Ballester, Acc. Chem. Res. 2013, 46, 874;
M. M. Watt, M. S. Sollins, D. W. Johnson, Acc. Chem. Res. 2013, 46, 955;
A. Vargas Jentzsch, A. Hennig, J. Mareda, S. Matile, Acc. Chem. Res. 2013, 46, 2791;
M. Giese, M. Albrecht, K. Rissanen, Chem. Rev. 2015, 115, 8867.
M. Mascal, A. Armstrong, M. D. Bartberger, J. Am. Chem. Soc. 2002, 124, 6274;
D. Quiñonero, C. Garau, C. Rotger, A. Frontera, P. Ballester, A. Costa, P. M. Deya, Angew. Chem. Int. Ed. 2002, 41, 3389;
Angew. Chem. 2002, 114, 3539;
I. Alkorta, I. Rozas, J. Elguero, J. Am. Chem. Soc. 2002, 124, 8593.
P. de Hoog, P. Gamez, I. Mutikainen, U. Turpeinen, J. Reedijk, Angew. Chem. Int. Ed. 2004, 43, 5815;
Angew. Chem. 2004, 116, 5939;
S. Demeshko, S. Dechert, F. Meyer, J. Am. Chem. Soc. 2004, 126, 4508;
Y. S. Rosokha, S. V. Lindeman, S. V. Rosokha, J. K. Kochi, Angew. Chem. Int. Ed. 2004, 43, 4650;
Angew. Chem. 2004, 116, 4750;
H. T. Chifotides, B. L. Schottel, K. R. Dunbar, Angew. Chem. Int. Ed. 2010, 49, 7202;
Angew. Chem. 2010, 122, 7360;
Y. Chen, D.-X. Wang, Z.-T. Huang, M.-X. Wang, Chem. Commun. 2011, 47, 8112;
J. Luo, Y.-F. Ao, C. Malm, J. Hunger, Q.-Q. Wang, D.-X. Wang, Dalton Trans. 2018, 47, 7883.
Q. He, Y. Han, Y. Wang, Z.-T. Huang, D.-X. Wang, Chem. Eur. J. 2014, 20, 7486;
Q. He, Y.-F. Ao, Z.-T. Huang, D.-X. Wang, Angew. Chem. Int. Ed. 2015, 54, 11785;
Angew. Chem. 2015, 127, 11951;
R.-B. Xu, Q.-Q. Wang, Y.-F. Ao, Z.-Y. Li, Z.-T. Huang, D.-X. Wang, Org. Lett. 2017, 19, 738;
D.-H. Tuo, W. Liu, X.-Y. Wang, X.-D. Wang, Y.-F. Ao, Q.-Q. Wang, Z.-Y. Li, D.-X. Wang, J. Am. Chem. Soc. 2019, 141, 1118.
V. Gorteau, G. Bollot, J. Mareda, A. Perez-Velasco, S. Matile, J. Am. Chem. Soc. 2006, 128, 14788;
X.-D. Wang, S. Li, Y.-F. Ao, Q.-Q. Wang, Z.-T. Huang, D.-X. Wang, Org. Biomol. Chem. 2016, 14, 330.
Y. J. Zhao, Y. Domoto, E. Orentas, C. Beuchat, D. Emery, J. Mareda, N. Sakai, S. Matile, Angew. Chem. Int. Ed. 2013, 52, 9940;
Angew. Chem. 2013, 125, 10124;
Y. Zhao, Y. Cotelle, L. Liu, J. López-Andarias, A. Bornhof, M. Akamatsu, N. Sakai, S. Matile, Acc. Chem. Res. 2018, 51, 2255.
C. Estarellas, A. Frontera, D. Quiñonero, P. M. Deyà, Angew. Chem. Int. Ed. 2011, 50, 415;
Angew. Chem. 2011, 123, 435;
M. Giese, M. Albrecht, K. Rissanen, Chem. Commun. 2016, 52, 1778;
X. Lucas, A. Bauzá, A. Frontera, D. Quiñonero, Chem. Sci. 2016, 7, 1038.
O. B. Berryman, F. Hof, M. J. Hynes, D. W. Johnson, Chem. Commun. 2006, 506;
O. B. Berryman, A. C. Sather, B. P. Hay, J. S. Meisner, D. W. Johnson, J. Am. Chem. Soc. 2008, 130, 10895;
M. Mascal, I. Yakovlev, E. B. Nikitin, J. C. Fettinger, Angew. Chem. Int. Ed. 2007, 46, 8782;
Angew. Chem. 2007, 119, 8938;
S. Guha, S. Saha, J. Am. Chem. Soc. 2010, 132, 17674;
M. Giese, M. Albrecht, T. Krappitz, M. Peters, V. Gossen, G. Raabe, A. Valkonen, K. Rissanen, Chem. Commun. 2012, 48, 9983.
D.-X. Wang, Q.-Y. Zheng, Q.-Q. Wang, M.-X. Wang, Angew. Chem. Int. Ed. 2008, 47, 7485;
Angew. Chem. 2008, 120, 7595;
D.-X. Wang, M.-X. Wang, J. Am. Chem. Soc. 2013, 135, 892;
D.-X. Wang, Q.-Q. Wang, Y. Han, Y. Wang, Z.-T. Huang, M.-X. Wang, Chem. Eur. J. 2010, 16, 13053;
S. Li, S.-X. Fa, Q.-Q. Wang, D.-X. Wang, M.-X. Wang, J. Org. Chem. 2012, 77, 1860.
G. Gil-Ramírez, E. C. Escudero-Adán, J. Bene tBuchholz, P. Ballester, Angew. Chem. Int. Ed. 2008, 47, 4114;
Angew. Chem. 2008, 120, 4182;
S. T. Schneebeli, M. Frasconi, Z. Liu, Y. Wu, D. M. Gardner, N. L. Strutt, C. Cheng, R. Carmieli, M. R. Wasielewski, J. F. Stoddart, Angew. Chem. Int. Ed. 2013, 52, 13100;
Angew. Chem. 2013, 125, 13338.
Q.-H. Guo, Z.-D. Fu, L. Zhao, M.-X. Wang, Angew. Chem. Int. Ed. 2014, 53, 13548;
Angew. Chem. 2014, 126, 13766;
M.-Y. Zhao, D.-X. Wang, M.-X. Wang, J. Org. Chem. 2018, 83, 1502;
H.-B. Liu, Q. Zhang, M.-X. Wang, Angew. Chem. Int. Ed. 2018, 57, 6536;
Angew. Chem. 2018, 130, 6646.
E. Graf, J.-M. Lehn, J. Am. Chem. Soc. 1975, 97, 5022;
F. P. Schmidtchen, Angew. Chem. Int. Ed. Engl. 1977, 16, 720;
Angew. Chem. 1977, 89, 751;
H. Takemura, T. Shinmyozu, T. Inazu, J. Am. Chem. Soc. 1991, 113, 1323;
P. Rajakumar, R. Padmanabhan, Tetrahedron Lett. 2010, 51, 1059;
Q.-Q. Wang, V. W. Day, K. Bowman-James, Angew. Chem. Int. Ed. 2012, 51, 2119;
Angew. Chem. 2012, 124, 2161;
Q.-Q. Wang, V. W. Day, K. Bowman-James, J. Am. Chem. Soc. 2013, 135, 392.
P. Skowronek, J. Gawronski, Org. Lett. 2008, 10, 4755;
M. Mastalerz, Chem. Commun. 2008, 4756;
T. Tozawa, J. T. A. Jones, S. I. Swamy, S. Jiang, D. J. Adams, S. Shakespeare, R. Clowes, D. Bradshaw, T. Hasell, S. Y. Chong, C. Tang, S. Thompson, J. Parker, A. Trewin, J. Bacsa, A. M. Z. Slawin, A. Steiner, A. I. Cooper, Nat. Mater. 2009, 8, 973;
T. Jiao, L. Chen, D. Yang, X. Li, G. Wu, P. Zeng, A. Zhou, Q. Yin, Y. Pan, B. Wu, X. Hong, X. Kong, V. M. Lynch, J. L. Sessler, H. Li, Angew. Chem. Int. Ed. 2017, 56, 14545;
Angew. Chem. 2017, 129, 14737.
J. Luo, Y.-F. Ao, Q.-Q. Wang, D.-X. Wang, Angew. Chem. Int. Ed. 2018, 57, 15827;
Angew. Chem. 2018, 130, 16053.
Q.-Q. Wang, D.-X. Wang, H.-B. Yang, Z.-T. Huang, M.-X. Wang, Chem. Eur. J. 2010, 16, 7265-7275;
Z.-C. Wu, Q.-H. Guo, M.-X. Wang, Angew. Chem. Int. Ed. 2017, 56, 7151;
Angew. Chem. 2017, 129, 7257;
W. J. Ong, T. M. Swager, Nature Chem. 2018, 10, 1023.
X.-B. Wang, J. Phys. Chem. A 2017, 121, 1389.
J. Zhang, B. Zhou, Z.-R. Sun, X.-B. Wang, Phys. Chem. Chem. Phys. 2015, 17, 3131.
C. S. Anstöter, J. P. Rogers, J. R. R. Verlet, J. Am. Chem. Soc. 2019, 141, 6132.
A. I. Boldyrev, J. Simons, J. Phys. Chem. 1994, 98, 2298;
X.-B. Wang, J. B. Nicholas, L.-S. Wang, J. Phys. Chem. A 2000, 104, 504;
X.-B. Wang, L.-S. Wang, J. Chem. Phys. 2000, 113, 10928.