Organic Letters
Letter
partial sigmoidal curve, indicating a cooperative assembly
that, like 1a, macrocycles 1c, 1g, 1i, and 1k also stack into helical
assemblies. The additional band around 390 nm in the spectra of
L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chim.
Acta 1997, 80, 173. (c) Gattuso, G.; Menzer, S.; Nepogodiev, S. A.;
Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1451.
(d) Mindyuk, O. Y.; Stetzer, M. R.; Heiney, P. A.; Nelson, J. C.; Moore, J.
S. Adv. Mater. 1998, 10, 1363. (e) Fritzsche, M.; Bohle, A.; Dudenko, D.;
Baumeister, U.; Sebastiani, D.; Richardt, G.; Spiess, H. W.; Hansen, M.
R.; Hoger, S. Angew. Chem., Int. Ed. 2011, 50, 3030. (f) Frischmann, P.
̈
D.; Sahli, B. J.; Guieu, S.; Patrick, B. O.; MacLachlan, M. J. Chem. - Eur. J.
2012, 18, 13712. (g) Hjelmgaard, T.; Roy, O.; Nauton, L.; El-Ghozzi,
M.; Avignant, D.; Didierjean, C.; Taillefumier, C.; Faure, S. Chem.
Commun. 2014, 50, 3564. (h) Zhao, H. Q.; Sheng, S.; Hong, Y. H.; Zeng,
H. Q. J. Am. Chem. Soc. 2014, 136, 14270.
1
k is due to the red-shifted B-band caused by π−π* transition
associated with the two benzene rings bearing amino groups.
In CHCl , macrocycles 1c, 1g, and 1i give CD signals with the
3
1
k measured in CCl and CHCl thus indicate that the strength
4 3
of its stacking interaction is reduced due to the presence of the
two amino groups.
(
4) (a) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28,
07. (b) Grave, C.; Schluter, A. D. Eur. J. Org. Chem. 2002, 3075.
c) Zhao, D. H.; Moore, J. S. Chem. Commun. 2003, 807. (d) Yamaguchi,
Y.; Yoshida, Z.-I. Chem. - Eur. J. 2003, 9, 5430. (e) Hoger, S. Chem. - Eur.
J. 2004, 10, 1320.
5) (a) Moore, J. S.; Zhang, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 922.
b) Hoger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1996, 34,
713. (c) Hensel, V.; Schluter, A. D. Chem. - Eur. J. 1999, 5, 421. (d) Seo,
1
(
̈
In summary, Pd-catalyzed coupling of monomeric building
blocks leads to the generation of a variety of trimeric building
blocks. Pairwise combinations of the trimeric building precursors
make it possible to synthesize a large number of different
macrocycles 1 that bear different types of side chains and, more
importantly, have cavities featured by different substitution
patterns of introduced groups, which demonstrates the feasibility
̈
(
(
2
̈
̈
S. H.; Jones, T. V.; Seyler, H.; Peters, J. O.; Kim, T. H.; Chang, J. Y.; Tew,
G. N. J. Am. Chem. Soc. 2006, 128, 9264. (e) Yang, L. Q.; Zhong, L. J.;
Yamato, K.; Zhang, X. H.; Feng, W.; Deng, P. C.; Yuan, L. H.; Zeng, X.
C.; Gong, B. New J. Chem. 2009, 33, 729. (f) Sisco, S. W.; Moore, J. S. J.
Am. Chem. Soc. 2012, 134, 9114. (g) Aggarwal, A. V.; Thiessen, A.;
and efficiency of this strategy. In CCl , four representative
4
macrocycles with distinctly different inward-pointing functional
groups adopt the same helical tubular assembly previously
observed for macrocycles 1a but show different stacking strength.
The aggregation of the macrocycles is interrupted in solvents of
high polarity. The availability of cavity-modified m-PE macro-
cycles that stack into the same nanotubular motif offers new
opportunities for constructing self-assembling nanotubes con-
taining functionally diverse and tunable subnanometer pores.
Idelson, A.; Kalle, D.; Wu
Vogelsang, J.; Hoger, S.; Lupton, J. M. Nat. Chem. 2013, 5, 964.
h) Tahara, K.; Yamamoto, Y.; Gross, D. E.; Kozuma, H.; Arikuma, Y.;
̈
rsch, D.; Stangl, T.; Steiner, F.; Jester, S.-S.;
̈
(
Ohta, K.; Koizumi, Y.; Gao, Y.; Shimizu, Y.; Seki, S.; Kamada, K.; Moore,
J. S.; Tobe, Y. Chem. - Eur. J. 2013, 19, 11251.
(
6) Several examples of other rigid macrocycles: (a) Yuan, L. H.; Feng,
W.; Yamato, K.; Sanford, A. R.; Xu, D. G.; Guo, H.; Gong, B. J. Am.
Chem. Soc. 2004, 126, 11120. (b) Jiang, H.; Leger, J.-M.; Guionneau, P.;
ASSOCIATED CONTENT
Supporting Information
́
■
Huc, I. Org. Lett. 2004, 6, 2985. (c) Sessler, J. L.; Tomat, E.; Lynch, V. M.
Chem. Commun. 2006, 4486. (d) Nakao, K.; Nishimura, M.; Tamachi,
T.; Kuwatani, Y.; Miyasaka, H.; Nishinaga, T.; Iyoda, M. J. Am. Chem.
Soc. 2006, 128, 16740. (e) Holub, J. M.; Jang, H. J.; Kirshenbaum, K.
Org. Lett. 2007, 9, 3275. (f) Campbell, F.; Plante, J.; Carruthers, C.;
Hardie, M. J.; Prior, T. J.; Wilson, A. J. Chem. Commun. 2007, 2240.
*
S
(g) Qin, B.; Ren, C.; Ye, R.; Sun, C.; Chiad, K.; Chen, X.; Li, Z.; Xue, F.;
Su, H.; Chass, G. A.; Zeng, H. Q. J. Am. Chem. Soc. 2010, 132, 9564.
AUTHOR INFORMATION
(h) Lee, S.; Chen, C.-H.; Flood, A. H. Nat. Chem. 2013, 5, 704.
■
(7) Zhou, X. B.; Liu, G. D.; Yamato, K.; Shen, Y.; Cheng, R. X.; Wei, X.
X.; Bai, W. L.; Gao, Y.; Li, H.; Liu, Y.; Liu, F. T.; Czajkowsky, D. M.;
Wang, J. F.; Dabney, M. J.; Cai, Z. H.; Hu, J.; Bright, F. V.; He, L.; Zeng,
X. C.; Shao, Z. F.; Gong, B. Nat. Commun. 2012, 3, 949.
*
*
Notes
(8) Yamato, K.; Kline, M.; Gong, B. Chem. Commun. 2012, 48, 12142.
(9) Wu, X. X.; Liu, R.; Sathyamoorthy, B.; Yamato, K.; Liang, G. X.;
The authors declare no competing financial interest.
Shen, L.; Ma, S. F.; Sukumaran, D. K.; Szyperski, T.; Fang, W. H.; He, L.;
Chen, X. B.; Gong, B. J. Am. Chem. Soc. 2015, 137, 5879.
(10) Kline, M. A.; Wei, X. X.; Horner, I. J.; Liu, R.; Chen, S.; Chen, S.;
Yung, K. Y.; Yamato, K.; Cai, Z. H.; Bright, F. V.; Zeng, X. C.; Gong, B.
Chem. Sci. 2015, 6, 152−157.
ACKNOWLEDGMENTS
■
We thank the Natural Science Foundation of China (91227109)
and the US National Science Foundation (CHE-1306326 and
CBET-1512124) for support.
(11) Helsel, A. J.; Brown, A. L.; Yamato, K.; Feng, W.; Yuan, L. H.;
Clements, A.; Harding, S. V.; Szabo, G.; Shao, Z. F.; Gong, B. J. Am.
Chem. Soc. 2008, 130, 15784.
REFERENCES
■
(12) Wei, X. X.; Zhang, G. Q.; Shen, Y.; Zhong, Y. L.; Liu, R.; Yang, N.;
(
1) (a) Bayley, H.; Cremer, P. S. Nature 2001, 413, 226. (b) Sakai, N.;
Al-mkhaizim, F. Y.; Kline, M.; He, L.; Li, M. F.; Lu, Z. L.; Shao, Z. F.;
Gong, B. J. Am. Chem. Soc. 2016, 138, 2749.
Mareda, J.; Matile, S. Acc. Chem. Res. 2008, 41, 1354. (c) Rebek, J. Acc.
Chem. Res. 2009, 42, 1660. (d) Childers, W. S.; Ni, R.; Mehta, A. K.;
Lynn, D. G. Curr. Opin. Chem. Biol. 2009, 13, 652. (e) Gong, B.; Shao, Z.
F. Acc. Chem. Res. 2013, 46, 2856.
(
13) (a) Endres, A.; Maas, G. Tetrahedron 2002, 58, 3999.
b) Kraszkiewicz, L.; Sosnowski, M.; Skulski, L. Tetrahedron 2004, 60,
113. (c) Chang, K. J.; Kang, B. N.; Lee, M. H.; Jeong, K. S. J. Am. Chem.
Soc. 2005, 127, 12214.
(
9
(
2) (a) Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew.
Chem., Int. Ed. 2001, 40, 988. (b) Gin, D. L.; Gu, W. Q.; Pindzola, B. A.;
Zhou, W. J. Acc. Chem. Res. 2001, 34, 973. (c) Keizer, H. M.; Sijbesma, R.
P. Chem. Soc. Rev. 2005, 34, 226. (d) Block, M. A. B.; Kaiser, C.; Khan,
A.; Hecht, S. Top. Curr. Chem. 2005, 245, 89. (e) Pasini, D.; Ricci, M.
Curr. Org. Synth. 2007, 4, 59.
(
3) (a) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.;
Khazanovich, N. Nature 1993, 366, 324. (b) Seebach, D.; Matthews, J.
D
Org. Lett. XXXX, XXX, XXX−XXX