The Journal of Organic Chemistry
ARTICLE
’ ACKNOWLEDGMENT
(17) (a) Baxter, N. J.; Williamson, M. P.; Lilley, T. H.; Haslam, E.
J. Chem. Soc., Faraday Trans. 1996, 92, 231–234. (b) Martin, R. B. Chem.
Rev. 1996, 96, 3043–3064. (c) Shetty, A. S.; Zhang, J. S.; Moore, J. S.
J. Am. Chem. Soc. 1996, 118, 1019–1027. (d) W€urthner, F.; Thalacker, C.;
Diele, S.; Tschierske, C. Chem.—Eur. J. 2001, 7, 2245–2253. (e) Tobe,
Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda,
M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350–5364.
(f) Zhao, D. H.; Moore, J. S. Org. Biomol. Chem. 2003, 1, 3471–3491.
(18) Recently, Schenning and Meijer reported mechanistic insights
into supramolecular polymerizations: Smulders, M. M. J.; Nieuwenhuizen,
M. M. L.; de Greef, T. F. A.; van der Schoot, P.; Schenning, A. P. H. J.;
Meijer, E. W. Chem.—Eur. J. 2010, 16, 362–367. Based on their report, the
association mechanism of 1 was studied by using the UV/Vis absorption
spectroscopy. Plots of the degree of aggregation, Ragg, vs T display a clear
sigmoidal shape, indicating that the association obeys an isodesmic
mechanism (Figure S2 in Supporting Information).
This research work was supported by Grant-in-Aids for
Scientific Research (Nos.18350065, 21350066) of JSPS, a
Grant-in-Aid for Science Research (No.19022024) in a Priority
Area “Super-Hierarchical Structures” from MEXT, Japan, and
Yamada Science Foundation.
’ REFERENCES
(1) (a) Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning,
A. P. H. J. Chem. Rev. 2005, 105, 1491–1546. (b) Ariga, K.; Nakanishi, T.;
Hill, J. P. Curr. Opin. Colloid Interface Sci. 2007, 12, 106–120. (c) Sada,
K.; Takeuchi, M.; Fujita, N.; Numata, M.; Shinkai, S. Chem. Soc. Rev.
2007, 36, 415–435. (d) Ajayaghosh, A.; Praveen, V. K.; Vijayakumar, C.
Chem. Soc. Rev. 2008, 37, 109–122. (e) Palmer, L. C.; Stupp, S. I. Acc.
Chem. Res. 2008, 41, 1674–1684. (f) Praveen, V. K.; Babu, S. S.;
Vijayakumar, C.; Varghese, R.; Ajayaghosh, A. Bull. Chem. Soc. Jpn.
2008, 81, 1196–1211. (g) Hasegawa, M.; Iyoda, M. Chem. Soc. Rev. 2010,
39, 2420–2427. (h) Hui, J. K. H.; MacLachlan, M. J. Coord. Chem. Rev.
2010, 254, 2363–2390.
(2) (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133–3159.
(b) Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485–495. (c)
Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237–1247. (d) van
Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263–2266.
(e) Gronwald, O.; Shinkai, S. Chem.—Eur. J. 2001, 7, 4328–4334.
(f) George, M.; Weiss, R. G. Acc. Chem. Res. 2006, 39, 489–497.
(3) Hanabusa, K.; Okui, K.; Karaki, K.; Koyama, T.; Shirai, H.
J. Chem. Soc., Chem. Commun. 1992, 1371–1373.
(4) van Esch, J.; Schoonbeek, F.; de Loos, M.; Kooijman, H.; Spek,
A. L.; Kellogg, R. M.; Feringa, B. L. Chem.—Eur. J. 1999, 5, 937–950.
(5) Yoza, K.; Ono, Y.; Yoshihara, K.; Akao, T.; Shinmori, H.; Takeuchi,
M.; Shinkai, S.; Reinhoudt, D. N. Chem. Commun. 1998, 907–908.
(6) Murata, K.; Aoki, M.; Suzuki, T.; Harada, T.; Kawabata, H.;
Komori, T.; Ohseto, F.; Ueda, K.; Shinkai, S. J. Am. Chem. Soc. 1994,
116, 6664–6676.
(7) (a) Schenning, A. P. H. J.; Meijer, E. W. Chem. Commun. 2005,
3245–3258. (b) Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007,
40, 644–656.
(19) Ishi-I, T.; Murakami, K. I.; Imai, Y.; Mataka, S. J. Org. Chem.
2006, 71, 5752–5760.
(20) Kastler, M.; Pisula, W.; Wasserfallen, D.; Pakula, T.; Mullen, K.
J. Am. Chem. Soc. 2005, 127, 4286–4296.
(21) Ishi-i, T.; Kuwahara, R.; Takata, A.; Jeong, Y.; Sakurai, K.;
Mataka, S. Chem.—Eur. J. 2006, 12, 763–776.
(22) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb,
M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, J. T.; Kudin, K. N.;
Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci,
B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada,
M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima,
T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian,
H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.;
Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala,
P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.;
Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.;
Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.;
Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.;
Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.;
Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill,
P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.
Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004.
(23) Kolossvary, I.; Guida, W. C. J. Am. Chem. Soc. 1996, 118,
5011–5019.
(24) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.;
Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C.
J. Comput. Chem. 1990, 11, 440–467.
(25) Dehm, V.; Chen, Z. J.; Baumeister, U.; Prins, P.; Siebbeles,
L. D. A.; W€urthner, F. Org. Lett. 2007, 9, 1085–1088.
(26) Green, M. M.; Garetz, B. A.; Munoz, B.; Chang, H. P.; Hoke, S.;
Cooks, R. G. J. Am. Chem. Soc. 1995, 117, 4181–4182.
(27) Yashima, E.; Maeda, K.; Nishimura, T. Chem.—Eur. J. 2004, 10,
(8) Ishikawa, Y.; Kuwahara, H.; Kunitake, T. J. Am. Chem. Soc. 1994,
116, 5579–5591.
(9) Suzuki, M.; Yumoto, M.; Shirai, H.; Hanabusa, K. Chem.—Eur. J.
2008, 14, 2133–2144.
(10) (a) Messmore, B. W.; Hulvat, J. F.; Sone, E. D.; Stupp, S. I.
J. Am. Chem. Soc. 2004, 126, 14452–14458. (b) Zang, L.; Che, Y.; Moore,
J. S. Acc. Chem. Res. 2008, 41, 1596–1608. (c) Bhattacharya, S.; Samanta,
S. K. Langmuir 2009, 25, 8378–8381. (d) Meijer, E. W.; De Greef,
T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma,
R. P. Chem. Rev. 2009, 109, 5687–5754.
42–51.
(28) (a) Jin, W.; Fukushima, T.; Niki, M.; Kosaka, A.; Ishii, N.; Aida,
T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10801–10806. (b) van Gestel,
J.; Palmans, A. R. A.; Titulaer, B.; Vekemans, J.; Meijer, E. W. J. Am.
Chem. Soc. 2005, 127, 5490–5494. (c) Wilson, A. J.; van Gestel, J.;
Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 2006, 4404–4406.
(29) (a) Green, M. M.; Reidy, M. P.; Johnson, R. J.; Darling, G.;
Oleary, D. J.; Willson, G. J. Am. Chem. Soc. 1989, 111, 6452–6454.
(b) Palmans, A. R. A.; Vekemans, J.; Havinga, E. E.; Meijer, E. W. Angew.
Chem., Int. Ed. 1997, 36, 2648–2651. (c) Ajayaghosh, A.; Varghese, R.;
George, S. J.; Vijayakumar, C. Angew. Chem., Int. Ed. 2006, 45, 1141–1144.
(30) Tanaka, M.; Haino, T.; Ideta, K.; Kubo, K.; Mori, A.; Fukazawa,
Y. Tetrahedron 2006, 63, 652–665.
(31) Budzik, B. W.; Evans, K. A.; Wisnoski, D. D.; Jin, J.; Rivero,
R. A.; Szewczyk, G. R.; Jayawickreme, C.; Moncol, D. L.; Yu, H. Bioorg.
Med. Chem. Lett. 2010, 20, 1363–1367.
(32) Keith, C.; Reddy, R. A.; Hauser, A.; Baumeister, U.; Tschierske,
C. J. Am. Chem. Soc. 2006, 128, 3051–3066.
(11) (a) Ishi-i, T.; Shinkai, S. Supramol. Dye Chem. 2005, 258,
119–160. (b) Iyoda, M.; Hasegawa, M.; Enozawa, H. Chem. Lett. 2007,
36, 1402–1407.
(12) (a) Brotin, T.; Utermohlen, R.; Fages, F.; Bouaslaurent, H.;
Desvergne, J. P. J. Chem. Soc., Chem. Commun. 1991, 416–418. (b)
Clavier, G.; Mistry, M.; Fages, F.; Pozzo, J. L. Tetrahedron Lett. 1999,
40, 9021–9024. (c) Mamiya, J.; Kanie, K.; Hiyama, T.; Ikeda, T.; Kato, T.
Chem. Commun. 2002, 1870–1871. (d) W€urthner, F.; Yao, S.; Beginn, U.
Angew. Chem., Int. Ed. 2003, 42, 3247–3250. (e) An, B. K.; Lee, D. S.;
Lee, J. S.; Park, Y. S.; Song, H. S.; Park, S. Y. J. Am. Chem. Soc. 2004,
126, 10232–10233. (f) Morita, Y.; Tasaka, T.; Kawabe, K.; Okamoto, H.;
Takenaka, S.; Kita, H. Mol. Cryst. Liq. Cryst. 2005, 435, 813–822.
(13) (a) Haino, T.; Tanaka, M.; Fukazawa, Y. Chem. Commun.
2008, 468–470. (b) Haino, T.; Saito, H. Synth. Met. 2009, 159, 821–826.
(14) Haino, T.; Saito, H. Aust. J. Chem. 2010, 63, 640–645.
(15) Murata, K.; Aoki, M.; Nishi, T.; Ikeda, A.; Shinkai, S. J. Chem.
Soc., Chem. Commun. 1991, 1715–1718.
(33) Lee, S. J.; Park, C. R.; Chang, J. Y. Langmuir 2004, 20, 9513–9519.
(16) John, G.; Jung, J. H.; Minamikawa, H.; Yoshida, K.; Shimizu, T.
Chem.—Eur. J. 2002, 8, 5494–5500.
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dx.doi.org/10.1021/jo200766u |J. Org. Chem. 2011, 76, 5082–5091