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A. Frontera, P. Ballester, A. Costa and P. M. Deya, Angew. Chem.,
Int. Ed., 2002, 41, 3389–3392; (c) I. Alkorta, I. Rozas and J. Elguero,
J. Am. Chem. Soc., 2002, 124, 8593–8598; (d) D. Kim, P. Tarakeshwar
and K. S. Kim, J. Phys. Chem. A, 2004, 108, 1250–1258.
the self-assembled aggregates from vesicles to micelles were
achieved through elaborate variation of the polarity and hydro-
philicity of the substituents attached on the larger rim of triazine
8 (a) O. B. Berryman, V. S. Bryantsev, D. P. Stay, D. W. Johnson and
B. P. Hay, J. Am. Chem. Soc., 2007, 129, 48–58; (b) Y. S. Rosokha, S. V.
Lindeman, S. V. Rosokha and J. K. Kochi, Angew. Chem., Int. Ed., 2004, 43,
4650–4652; (c) H. T. Chifotides, B. L. Schottel and K. R. Dunbar, Angew.
rings. The vesicular entities of 3a were responsive to anions,
ꢀ
following a selectivity in the order NO3ꢀ 4 Clꢀ 4 Brꢀ 4 ClO4
,
as a result of cooperative anion–p interactions and hydrogen
bonding between the surface engineered macrocyclic cavities
and anions. This study has convincingly shown the potential of
heteracalixaromatics for future applications in the design of
anion responsive materials21 in supramolecular chemistry.
This work was financially supported by MOST (2011CB932501,
2013CB834504), NNSFC (91127008, 21272239).
´
Chem., Int. Ed., 2010, 49, 7202–7207; (d) G. Gil-Ramırez, E. C. Escudero-
´
Adan, J. Benet-Buchholz and P. Ballester, Angew. Chem., Int. Ed., 2008, 47,
4114–4118; (e) M. Giese, M. Albrecht, T. Krappitz, M. Peters, V. Gossen,
G. Raabe, A. Valkonen and K. Rissanen, Chem. Commun., 2012, 48,
´
9983–9985; ( f ) P. Arranz-Mascaros, C. Bazzicalupi, A. Bianchi, C. Giorgi,
´
´
M.-L. Godino-Salido, M.-D. Gutierrez-Valero, R. Lopez-Garzon and
M. Savastano, J. Am. Chem. Soc., 2013, 135, 102–105.
9 (a) T. Davis, Nat. Chem., 2010, 2, 516–517; (b) A. V. Jentzsch, A. Hennig,
J. Mareda and S. Matile, Acc. Chem. Res., 2013, 46, 2791–2800.
10 S. Guha and S. Saha, J. Am. Chem. Soc., 2010, 132, 17674–17677.
11 V. Gorteau, G. Bollot, J. Mareda, A. Perez-Velasco and S. Matile,
J. Am. Chem. Soc., 2006, 128, 14788–14789.
12 (a) Y. Zhao, C. Beuchat, Y. Domoto, J. Gajewy, A. Wilson, J. Mareda,
N. Sakai and S. Matile, J. Am. Chem. Soc., 2014, 136, 2101–2111;
(b) Y. Zhao, Y. Domoto, E. Orentas, C. Beuchat, D. Emery, J. Mareda,
N. Sakai and S. Matile, Angew. Chem., Int. Ed., 2013, 52, 9940–9943.
13 Q. He, Y. Han, Y. Wang, Z.-T. Huang and D.-X. Wang, Chem. – Eur. J.,
2014, 20, 7486–7491.
14 K. Kalyanasundaram and J. K. Thomas, J. Am. Chem. Soc., 1977, 99,
2039–2044.
15 (a) S. Arimori, T. Nagasaki and S. Shinkai, J. Chem. Soc., Perkin Trans.
2, 1995, 679–683; (b) J. Kubitschke, S. Javor and J. Rebek, Chem.
Commun., 2012, 48, 9251–9253.
Notes and references
1 (a) M.-X. Wang, Acc. Chem. Res., 2012, 45, 182–195; (b) M.-X. Wang,
Chem. Commun., 2008, 6612; (c) W. Maes and W. Dehaen, Chem. Soc.
Rev., 2008, 37, 2393–2402; (d) H. Tsue, K. Ishibashi and R. Tamura,
Top. Heterocycl. Chem., 2008, 17, 73–96.
2 (a) H.-Y. Gong, Q.-Y. Zheng, X.-H. Zhang, D.-X. Wang and M.-X.
Wang, Org. Lett., 2006, 8, 4895–4898; (b) C.-Y. Gao, L. Zhao and M.-X.
Wang, J. Am. Chem. Soc., 2011, 133, 8448–8451; (c) C.-Y. Gao, L. Zhao
and M.-X. Wang, J. Am. Chem. Soc., 2012, 134, 824–827.
3 (a) H.-Y. Gong, D.-X. Wang, J.-F. Xiang, Q.-Y. Zheng and M.-X. Wang,
Chem. – Eur. J., 2007, 13, 7791–7802; (b) Q.-Q. Wang, D.-X. Wang,
H.-B. Yang, Z.-T. Huang and M.-X. Wang, Chem. – Eur. J., 2010, 16,
7265–7275.
16 P. Ballinger and F. A. Long, J. Am. Chem. Soc., 1960, 82, 795–798.
17 M. H. K. Ebbing, M.-J. Villa, J.-M. Valpuesta, P. Prados and J. de
Mendoza, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 4962–4966.
18 (a) M. Lee, S. J. Lee and L. H. Jiang, J. Am. Chem. Soc., 2004, 126,
12724–12725; (b) O. M. Martin and S. Mecozzi, Supramol. Chem., 2005, 17,
9–15; (c) G. M. L. Consoli, G. Granata, R. Lo Nigro, G. Malandrino and
C. Geraci, Langmuir, 2008, 24, 6194–6200; (d) K. Suwinska, O. Shkurenko,
C. Mbemba, A. Leydier, S. Jebors, A. W. Coleman, R. Matar and P. Falson,
New J. Chem., 2008, 32, 1988–1998; (e) D.-S. Guo, K. Wang, Y.-X. Wang and
Y. Liu, J. Am. Chem. Soc., 2012, 134, 10244–10250; ( f ) R. V. Rodik, A. S.
Klymchenko, N. Jain, S. I. Miroshnichenko, L. Richert, V. I. Kalchenko
and Y. Mely, Chem. – Eur. J., 2011, 17, 5526–5538.
19 R. V. Vico, J. Voskuhl and B. J. Ravoo, Langmuir, 2011, 27, 1391–1397.
20 M. R. Ajayakumar and P. Mukhopadhyay, Org. Lett., 2010, 12,
2646–2649.
21 (a) H. Maeda, Chem. – Eur. J., 2008, 14, 11274–11282; (b) D. Asthana,
R. Pandey and P. Mukhopadhyay, Chem. Commun., 2013, 49, 451–453;
(c) J. A. Foster, M.-O. Piepenbrock, G. O. Lloyd, N. Clarke,
J. A. K. Howard and J. W. Steed, Nat. Chem., 2010, 2, 1037–1043.
4 (a) D.-X. Wang, Q.-Y. Zheng, Q.-Q. Wang and M.-X. Wang, Angew.
Chem., Int. Ed., 2008, 47, 7485–7488; (b) D.-X. Wang and M.-X. Wang,
J. Am. Chem. Soc., 2013, 135, 892–897; (c) D.-X. Wang, Q.-Q. Wang,
Y. Han, Y. Wang, Z.-T. Huang and M.-X. Wang, Chem. – Eur. J., 2010,
16, 13053–13057.
5 (a) H.-B. Yang, D.-X. Wang, Q.-Q. Wang and M.-X. Wang, J. Org.
Chem., 2007, 72, 3757–3763; (b) W. Van Rossom, W. Maes,
L. Kishore, M. Ovaere, L. Van Meervelt and W. Dehaen, Org. Lett.,
2008, 10, 585–588; (c) B.-Y. Hou, D.-X. Wang, H.-B. Yang, Q.-Y. Zheng
and M.-X. Wang, J. Org. Chem., 2007, 72, 5218–5226.
6 (a) A. Frontera, P. Gamez, M. Mascal, T. J. Mooibroek and J. Reedijk,
Angew. Chem., Int. Ed., 2011, 50, 9564–9583; (b) H. T. Chifotides and
K. R. Dunbar, Acc. Chem. Res., 2013, 46, 894–906; (c) P. Gamez,
T. J. Mooibroek, S. J. Teat and J. Reedijk, Acc. Chem. Res., 2007, 40,
435–444; (d) B. P. Hay and V. S. Bryantsev, Chem. Commun., 2008,
2417–2428; (e) D.-X. Wang and M.-X. Wang, Chimia, 2011, 65,
939–943; ( f ) P. Ballester, Acc. Chem. Res., 2013, 46, 874–884.
7 (a) M. Mascal, A. Armstrong and M. D. Bartberger, J. Am. Chem. Soc.,
2002, 124, 6274–6276; (b) D. Quinonero, C. Garau, C. Rotger,
12988 | Chem. Commun., 2014, 50, 12985--12988
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