Angewandte
Communications
Chemie
[7] J. P. Byrne, J. A. Kitchen, T. Gunnlaugsson, Chem. Soc. Rev.
Herein, we have demonstrated the formation of mechan-
ically interlocked structures by use of the btp ligand motif. We
have shown that these structures are formed by favorable self-
templating hydrogen-bonding interactions that are non-
amide-based. We further showed that these interactions can
be employed for anion recognition, whereby a strong bias was
observed for H2PO4À. This selective recognition reflects the
structural nature of the [2]catenane host. Further studies to
fully understand the relationship between the [2]catenane
structure and its anion-binding behavior and to extend the
application of this molecular recognition in functional supra-
molecular chemistry are in progress in our laboratory.
2014, 43, 5302.
[8] a) G. Schill, A. Lꢄttringhaus, Angew. Chem. Int. Ed. Engl. 1964,
3, 546; Angew. Chem. 1964, 76, 567; b) G. Gil-Ramꢃrez, D. A.
Leigh, A. J. Stephens, Angew. Chem. Int. Ed. 2015, 54, 6110;
Angew. Chem. 2015, 127, 6208; c) M. Xue, Y. Yang, X. Chi, X.
Yan, F. Huang, Chem. Rev. 2015, 115, 7398; d) J. F. Stoddart,
Chem. Soc. Rev. 2009, 38, 1802; e) J. C. Barnes, A. C. Fahren-
bach, D. Cao, S. M. Dyar, M. Frasconi, M. A. Giesener, D.
Benꢃtez, E. Tkatchouk, O. Chernyashevskyy, W. H. Shin, H. Li,
S. Sampath, C. L. Stern, A. A. Sarjeant, K. J. Hartlieb, Z. C. Liu,
R. Carmieli, Y. Y. Botros, J. W. Choi, A. M. Z. Slawin, J. B.
Ketterson, M. R. Wasielewski, W. A. Goddard, J. F. Stoddart,
Science 2013, 339, 429; f) R. S. Forgan, J.-P. Sauvage, J. F.
Stoddart, Chem. Rev. 2011, 111, 5434; g) D. Amabilino, J. F.
Stoddart, Chem. Rev. 1995, 95, 2725.
[9] a) C. O. Dietrich-Buchecker, J. P. Sauvage, J. M. Kern, J. Am.
Chem. Soc. 1984, 106, 3043; b) C. O. Dietrich-Buchecker, J.-P.
Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095;
c) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington,
A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vincent, D. J.
Williams, Angew. Chem. Int. Ed. Engl. 1989, 28, 1396; Angew.
Chem. 1989, 101, 1404.
[10] a) R. J. Bordoli, S. M. Goldup, J. Am. Chem. Soc. 2014, 136,
4817; b) J. D. Crowley, S. M. Goldup, A.-L. Lee, D. A. Leigh,
R. T. McBurney, Chem. Soc. Rev. 2009, 38, 1530; c) S. M.
Goldup, D. A. Leigh, T. Long, P. R. McGonigal, M. D. Symes,
J. Wu, J. Am. Chem. Soc. 2009, 131, 15924; d) S. M. Goldup,
D. A. Leigh, P. J. Lusby, R. T. McBurney, A. M. Z. Slawin,
Angew. Chem. Int. Ed. 2008, 47, 6999; Angew. Chem. 2008, 120,
7107; e) H. Lahlali, K. Jobe, M. Watkinson, S. M. Goldup,
Angew. Chem. Int. Ed. 2011, 50, 4151; Angew. Chem. 2011, 123,
4237; f) J. Winn, A. Pinczewska, S. M. Goldup, J. Am. Chem. Soc.
2013, 135, 13318.
[11] a) H. Li, H. Zhang, A. D. Lammer, M. Wang, X. Li, V. M. Lynch,
J. L. Sessler, Nat. Chem. 2015, 7, 1003; b) T. Hasell, X. F. Wu,
J. T. A. Jones, J. Basca, A. Steiner, T. Mitra, A. Trewin, D. J.
Adams, A. I. Cooper, Nat. Chem. 2010, 2, 750; c) J. C. Loren, P.
Gantzel, A. Linden, J. S. Siegel, Org. Biomol. Chem. 2005, 3,
3105; d) R. Mitra, M. Thiele, F. Octa-Smolin, M. C. Letzel, J.
Niemeyer, Chem. Commun. 2016, 52, 5977.
[12] a) M. Weck, B. Mohr, J.-P. Sauvage, R. H. Grubbs, J. Org. Chem.
1999, 64, 5463; b) B. Mohr, J.-P. Sauvage, R. H. Grubbs, M.
Weck, Angew. Chem. Int. Ed. Engl. 1997, 36, 1308; Angew.
Chem. 1997, 109, 1365.
Acknowledgements
We thank the Irish Research Council (IRC, J.P.B.), TCD
School of Chemistry (A.B.A.), Science Foundation Ireland
(SFI; for PI 2013 13/IA/1865 grant, T.G.), and the EU
Commission (Marie Curie Fellowship, S.B.) for financially
supporting this research.
Keywords: anion hosts · catenanes · ring-closing metathesis ·
self-templating · triazoles
[1] a) J. P. Byrne, J. A. Kitchen, O. Kotova, V. Leigh, A. Bell, J. J.
Boland, M. Albrecht, T. Gunnlaugsson, Dalton Trans. 2014, 43,
196; b) B. Schulze, C. Friebe, M. D. Hager, A. Winter, R.
Hoogenboom, H. Gorls, U. S. Schubert, Dalton Trans. 2009, 787;
c) M. Ostermeier, M.-A. Berlin, R. M. Meudtner, S. Demeshko,
F. Meyer, C. Limberg, S. Hecht, Chem. Eur. J. 2010, 16, 10202;
d) R. M. Meudtner, M. Ostermeier, R. Goddard, C. Limberg, S.
Hecht, Chem. Eur. J. 2007, 13, 9834; e) A. H. Younes, R. J. Clark,
L. Zhu, Supramol. Chem. 2012, 24, 696; f) Y. Li, L. Zhao, A. Y.-
Y. Tam, K. M.-C. Wong, L. Wu, V. W.-W. Yam, Chem. Eur. J.
2013, 19, 14496.
[2] a) J. P. Byrne, J. A. Kitchen, J. E. OꢁBrien, R. D. Peacock, T.
Gunnlaugsson, Inorg. Chem. 2015, 54, 1426; b) E. Brunet,
H. M. H. Alhendawi, O. Juanes, L. Jimꢂnez, J. C. Rodrꢃguez-
Ubis, J. Mater. Chem. 2009, 19, 2494; c) E. Brunet, L. Jimꢂnez,
M. de Victoria-Rodriguez, V. Luu, G. Muller, O. Juanes, J. C.
Rodrꢃguez-Ubis, Microporous Mesoporous Mater. 2013, 169,
222; d) E. Brunet, O. Juanes, L. Jimꢂnez, J. C. Rodrꢃguez-Ubis,
Tetrahedron Lett. 2009, 50, 5361; e) A. Indapurkar, B. Henriksen,
J. Tolman, J. Fletcher, J. Pharm. Sci. 2013, 102, 2589; f) L.
Munuera, R. K. OꢁReilly, Dalton Trans. 2010, 39, 388.
[3] a) Y. Li, A. H. Flood, J. Am. Chem. Soc. 2008, 130, 12111; b) Y.
Li, M. Pink, J. A. Karty, A. H. Flood, J. Am. Chem. Soc. 2008,
130, 17293.
[4] a) S. J. Bradberry, J. P. Byrne, C. P. McCoy, T. Gunnlaugsson,
Chem. Commun. 2015, 51, 16565; b) G. C. Midya, S. Paladhi, S.
Bhowmik, S. Saha, J. Dash, Org. Biomol. Chem. 2013, 11, 3057.
[5] S. Wang, J. A. Cuesta-Seijo, D. Lafont, M. M. Palcic, S. Vidal,
Chem. Eur. J. 2013, 19, 15346.
[6] a) E. P. McCarney, J. P. Byrne, B. Twamley, M. Martꢃnez-Calvo,
G. Ryan, M. E. Mçbius, T. Gunnlaugsson, Chem. Commun.
2015, 51, 14123; b) B. Yang, H. Zhang, H. Peng, Y. Xu, B. Wu, W.
Weng, L. Li, Polym. Chem. 2014, 5, 1945; c) J. Yuan, X. Fang, L.
Zhang, G. Hong, Y. Lin, Q. Zheng, Y. Xu, Y. Ruan, W. Weng, H.
Xia, G. Chen, J. Mater. Chem. 2012, 22, 11515.
[13] D. A. Leigh, P. J. Lusby, R. T. McBurney, A. Morelli, A. M. Z.
Slawin, A. R. Thomson, D. B. Walker, J. Am. Chem. Soc. 2009,
131, 3762.
[14] a) N. G. White, P. D. Beer, Chem. Commun. 2012, 48, 8499;
b) N. H. Evans, E. S. H. Allinson, M. D. Lankshear, K.-Y. Ng,
A. R. Cowley, C. J. Serpell, S. M. Santos, P. J. Costa, V. Felix,
P. D. Beer, RSC Adv. 2011, 1, 995; c) M. J. Langton, P. D. Beer,
Chem. Commun. 2014, 50, 8124; d) L. C. Gilday, T. Lang, A.
Caballero, P. J. Costa, V. Fꢂlix, P. D. Beer, Angew. Chem. Int. Ed.
2013, 52, 4356; Angew. Chem. 2013, 125, 4452.
[15] C. Lincheneau, B. Jean-Denis, T. Gunnlaugsson, Chem.
Commun. 2014, 50, 2857.
[16] a) J.-F. Ayme, G. Gil-Ramꢃrez, D. A. Leigh, J.-F. Lemonnier, A.
Markevicius, C. A. Muryn, G. Zhang, J. Am. Chem. Soc. 2014,
136, 13142; b) G. Zhang, G. Gil-Ramꢃrez, A. Markevicius, C.
Browne, I. J. Vitorica-Yrezabal, D. A. Leigh, J. Am. Chem. Soc.
2015, 137, 10437.
[17] a) C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303; b) H.
Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem.
Commun. 1995, 809.
[18] F. Vçgtle, S. Meier, R. Hoss, Angew. Chem. Int. Ed. Engl. 1992,
31, 1619; Angew. Chem. 1992, 104, 1628.
Angew. Chem. Int. Ed. 2016, 55, 1 – 7
ꢀ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5
These are not the final page numbers!