Journal of the American Chemical Society
COMMUNICATION
chirality and/or self-sorting phenomena in this type of layered
supramolecular copolymers.
Jiang, X.-K.; Chen, Y.-Q.; Li, Z.-T.; Chen, G.-J. J. Am. Chem. Soc. 2003,
125, 15128. (c) Folmer, B. J. B.; Sijbesma, R. P.; Meijer, E. W. J. Am.
Chem. Soc. 2001, 123, 2093. (d) Beijer, F. H.; Sijbesma, R. P.; Kooijman,
H.; Spek, A. L.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 6761.
(e) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710.
(8) (a) Martos, V.; Castreno, P.; Valero, J.; de Mendoza, J. Curr.
Opin. Chem. Biol. 2008, 12, 698. (b) Badjic, J. D.; Nelson, A.; Cantrill,
S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723.
(c) Mulder, A.; Huskens, J.; Reinhoudt, D. N. Org. Biomol. Chem. 2004,
2, 3409.
’ ASSOCIATED CONTENT
S
Supporting Information. General experimental proce-
b
dures, synthesis and characterization, 1H and 13C NMR spectra,
and additional UVÀvis and CD spectra. This material is available
(9) (a) Badjic, J. D.; Cantrill, S. J.; Stoddart, J. F. J. Am. Chem. Soc.
2004, 126, 2288. (b) Broeren, M. A. C.; van Dongen, J. L. J.; Pittelkow,
M.; Christensen, J. B.; van Genderen, M. H. P.; Meijer, E. W. Angew.
Chem., Int. Ed. 2004, 43, 3557. (c) Huskens, J.; Mulder, A.; Auletta, T.;
Nijhuis, C. A.; Ludden, M. J. W.; Reinhoudt, D. N. J. Am. Chem. Soc.
2004, 126, 6784. (d) Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Shao, X.-B.; Jiang,
X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2006, 128, 12307.
’ AUTHOR INFORMATION
Corresponding Author
xzhao@mail.sioc.ac.cn; ygma@pku.edu.cn; ztli@mail.sioc.ac.cn
’ ACKNOWLEDGMENT
(10) Yang, X.; Hua, F.; Yamato, K.; Ruckenstein, E.; Gong, B.; Kim,
W.; Ryu, C. Y. Angew. Chem., Int. Ed. 2004, 43, 6471.
We thank the National Natural Science Foundation and the
Ministry of Science and Technology of China (2007CB808001)
and the Science and Technology Committee of Shanghai Muni-
cipality (10PJ1412200 and 09XD1405300) for financial support.
(11) (a) Besenius, P.; Portale, G.; Bomans, P. H. H.; Janssen, H. M.;
Palmans, A. R. A.; Meijer, E. W. Proc. Natl. Acad. Sci. U.S.A. 2010,
107, 17888. (b) Stals, P. J. M.; Everts, J. C.; de Bruijn, R.; Filot, I. A. W.;
Smulders, M. M. J.; Martin-Rapun, R.; Pidko, E. A.; de Greef, T. F. A.;
Palmans, A. R. A.; Meijer, E. W. Chem.—Eur. J. 2010, 16, 810.
(12) Chen, S.-G.; Fu, Y.-C.; Wang, G.-T.; Li, G.-Y.; Ma, Y.; Jiang,
X.-K.; Li, Z.-T. Tetrahedron 2010, 66, 4057.
(13) (a) Kolotuchin, S. V.; Zimmerman, S. C. J. Am. Chem. Soc. 1998,
120, 9092. (b) Ma, Y.; Kolotuchin, S. V.; Zimmerman, S. C. J. Am. Chem.
Soc. 2002, 124, 13757.
(14) Koshland, D. E. Proc. Natl. Acad. Sci. U.S.A. 1958, 44, 98.
(15) Nishide, H.; Doi, R.; Oyaizu, K.; Tsuchida, E. J. Org. Chem.
2001, 66, 1680.
(16) Mammana, A.; Pescitelli, G.; Asakawa, T.; Jockusch, S.;
Petrovic, A. G.; Monaco, R. R.; Purrello, R.; Turro, N. J.; Nakanishi,
K.; Ellestad, G. A.; Balaz, M.; Berova, N. Chem.—Eur. J. 2009, 15, 11853.
(17) Berova, N.; Nakanishi, K.; Woody, R. W. Circular Dichroism;
Wiley-VCH: New York, 2000; p 338.
’ REFERENCES
(1) Ciferri, A. Supramolecular Polymers; Marcel-Dekker: New York,
2005.
(2) (a) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P.
Chem. Rev. 2001, 101, 4071. (b) Lehn, J.-M. Prog. Polym. Sci. 2005,
30, 814. (c) Harada, A.; Takashima, Y.; Yamaguchi, H. Chem. Soc. Rev.
2009, 38, 875. (d) Huang, F.; Gibson, H. W. Prog. Polym. Sci. 2005,
30, 982. (e) Rasa, M.; Schubert, U. S. Soft Matter 2006, 2, 561. (f) Serpe,
M. J.; Craig, S. L. Langmuir 2007, 23, 1626. (g) Rieth, S.; Baddeley, C.;
Badjic, J. D. Soft Matter 2007, 3, 137. (h) Weck, M. Polym. Int. 2007,
56, 453. (i) De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.;
Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Chem. Rev. 2009,
109, 5687. (j) Niu, Z.; Gibson, H. W. Chem. Rev. 2009, 109, 6024.
(k) Fox, J. D.; Rowan, S. J. Macromolecules 2009, 42, 6823. (l) Fang, L.;
Olson, M. A.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Stoddart,
J. F. Chem. Soc. Rev. 2010, 39, 17.
(3) (a) Wietor, J.-L.; van Beek, D. J. M.; Peters, G. W.; Mendes, E.;
Sijbesma, R. P. Macromolecules 2011, 44, 1211. (b) Smulders, M. M. J;
Filot, I. A. W; Leenders, J. M. A; van der Schoot, P.; Palmans, A. R. A;
Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2010, 132, 611.
(c) Shokrollahi, P.; Mirzadeh, H.; Huck, W. T. S.; Scherman, O. A.
Polymer 2010, 51, 6303. (d) Todd, E. M.; Zimmerman, S. C. Tetrahedron
2008, 64, 8558. (e) Leung, K. C.-F.; Mendes, P. M.; Magonov, S. N.;
Northrop, B. H.; Kim, S.; Patel, K.; Flood, A. H.; Tseng, H.-R.; Stoddart,
J. F. J. Am. Chem. Soc. 2006, 128, 10707.
(18) Wyatt, P. J. Anal. Chim. Acta 1993, 272, 1.
(19) Scanning electron microscopy and transmission electron mi-
croscopy measurements showed that the mixture of 1 and (R)-2
in toluene did not generate fibrous microstructures on the surface upon
evaporation of the solvent. In view of the weakness of the hydro-
gen bonding, it is reasonable to propose that upon transfer from the
solution to the surface, the (A)6ÀB supramolecular copolymers break
because the disklike hydrogen-bonded hexamer of 1 is not be stable
enough to stand on the surface. As a result, long layered aggregates were
not formed on the surface.
(4) (a) Miyawaki, A.; Takashima, Y.; Yamaguchi, H.; Harada, A.
Tetrahedron 2008, 64, 8355. (b) Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.;
Yu, Y.; Ma, Z.; Huang, F. Angew. Chem., Int. Ed. 2011, 50, 1397.
(5) (a) Burnworth, M.; Tang, L.; Kumpfer, J. R.; Duncan, A. J.;
Beyer, F. L.; Fiore, G. L.; Rowan, S. J.; Weder, C. Nature 2011, 472, 334.
(b) Xu, D.-H.; Liu, C.-Y.; Craig, S. L. Macromolecules 2011, 44, 2343.
(c) Jeon, S. L.; Loveless, D. M.; Craig, S. L. Supramol. Chem. 2010,
22, 697. (d) Kumpfer, J. R.; Jin, J.; Rowan, S. J. J. Mater. Chem. 2010,
20, 145. (e) Weng, W.; Li, Z.; Jamieson, A. M.; Rowan, S. J. Soft Matter
2009, 5, 4647. (f) Chiper, M.; Hoogenboom, R.; Schubert, U. S.
Macromol. Rapid Commun. 2009, 30, 565.
(6) (a) Niu, Z.; Huang, F.; Gibson, H. W. J. Am. Chem. Soc. 2011,
133, 2836. (b) Wang, F.; Zhang, J.; Ding, X.; Dong, S.; Liu, M.; Zheng,
B.; Li, S.; Wu, L.; Yu, Y.; Gibson, H. W.; Huang, F. Angew. Chem., Int. Ed.
2010, 49, 1090. (c) Lee, M.; Schoonover, D. V.; Gies, A. P.; Hercules,
D. M.; Gibson, H. W. Macromolecules 2009, 42, 6483. (d) Liu, Y.; Yu, Y.;
Gao, J.; Wang, Z.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 6576.
(7) (a) Blight, B. A.; Hunter, C. A.; Leigh, D. A.; McNab, H.;
Thomson, P. I. T. Nat. Chem. 2011, 3, 244. (b) Zhao, X.; Wang, X.-Z.;
11127
dx.doi.org/10.1021/ja205059z |J. Am. Chem. Soc. 2011, 133, 11124–11127