10.1002/asia.202000603
Chemistry - An Asian Journal
FULL PAPER
[1]
a) J. Rebek, Jr., Angew. Chem. Int. Ed. 2005, 44, 2068-2078; Angew.
Chem. 2005, 117, 2104-2115; b) M. Yoshizawa, J. K. Klosterman, M.
Fujita, Angew. Chem. Int. Ed. 2009, 48, 3418-3438; Angew. Chem. 2009,
121, 3470-3490; c) K. Kobayashi, M. Yamanaka, Chem. Soc. Rev. 2015,
44, 449-466; d) H. Sepehrpour, W. Fu, Y. Sun, P. J. Stang, J. Am. Chem.
Soc. 2019, 141, 14005-14020.
D. K. Chand, Chem. Eur. J. 2019, 25, 12241-12269; j) A. Kumar, P. S.
Mukherjee, Chem. Eur. J. 2020, 26, 4842-4849.
[10] For self-sorting for self-assembled capsules based on dynamic imine
bonds, see: a) K. Acharyya, S. Mukherjee, P. S. Mukherjee, J. Am. Chem.
Soc. 2013, 135, 554-557; b) D. Beaudoin, F. Rominger, M. Mastalerz,
Angew. Chem. Int. Ed. 2017, 56, 1244-1248; Angew. Chem. 2017, 129,
1264-1268; c) M. Kolodziejski, A. R. Stefankiewicz, J.-M. Lehn, Chem.
Sci. 2019, 10, 1836-1843; d) R. L. Greenaway, V. Santolini, A. Pulido, M.
A. Little, B. M. Alston, M. E. Briggs, G. M. Day, A. I. Cooper, K. E. Jelfs,
Angew. Chem. Int. Ed. 2019, 58, 16275-16281; Angew. Chem. 2019, 131,
16421-16427.
[2]
a) C. J. Brown, F. D. Toste, R. G. Bergman, K. N. Raymond, Chem. Rev.
2015, 115, 3012-3035; b) A. J. McConnell, C. S. Wood, P. P.
Neelakandan, J. R. Nitschke, Chem. Rev. 2015, 115, 7729-7793; c) L.
You, D. Zha, E. V. Anslyn, Chem. Rev. 2015, 115, 7840-7892.
[3]
[4]
For Pd(Py)2L2-based capsules, see: a) M. Fujita, M. Tominaga, A. Hori,
B. Therrien, Acc. Chem. Res. 2005, 38, 371-380; b) R. Chakrabarty, P.
S. Mukherjee, P. J. Stang, Chem. Rev. 2011, 111, 6810-6918.
[11] For chiral self-sorting, see: a) H. Jedrzejewska, A. Szumna, Chem. Rev.
2017, 117, 4863-4899; b) Ref. [9b]; c) Ref. [9e]; d) Ref. [9f]; e) Ref. [9g];
f) Ref. [10b].
For Pd(Py)4-based capsules, see: a) M. Tominaga, K. Suzuki, M.
Kawano, T. Kusukawa, T. Ozeki, S. Sakamoto, K. Yamaguchi, M. Fujita,
Angew. Chem. Int. Ed. 2004, 43, 5621-5625; Angew. Chem. 2004, 116,
5739-5743; b) S. Hiraoka, Y. Yamauchi, R. Arakane, M. Shionoya, J. Am.
Chem. Soc. 2009, 131, 11646-11647; c) N. Kishi, Z. Li, K. Yoza, M. Akita,
M. Yoshizawa, J. Am. Chem. Soc. 2011, 133, 11438-11441; d) K. Harris,
D. Fujita, M. Fujita, Chem. Commun. 2013, 49, 6703-6712; e) M. Han, D.
M. Engelhard, G. H. Clever, Chem. Soc. Rev. 2014, 43, 1848-1860; f) D.
Fujita, Y. Ueda, S. Sato, N. Mizuno, T. Kumasaka, M. Fujita, Nature 2016,
540, 563-566; g) D. P. August, G. S. Nichol, P. J. Lusby, Angew. Chem.
Int. Ed. 2016, 55, 15022-15026; Angew. Chem. 2016, 128, 15246-15250;
h) L. Escobar, E. C. Escudero-Adán, P. Ballester, Angew. Chem. Int. Ed.
2019, 58, 16105-16109; Angew. Chem. 2019, 131, 16251-16255.
For metal-coordination assisted tetrahedron- or octahedron-shaped
capsules, see: a) D. L. Caulder, K. N. Raymond, Acc. Chem. Res. 1999,
32, 975-982; b) S. Hiraoka, K. Harano, M. Shiro, Y. Ozawa, N. Yasuda,
K. Toriumi, M. Shionoya, Angew. Chem. Int. Ed. 2006, 45, 6488-6491;
Angew. Chem. 2006, 118, 6638-6641; c) A. M. Castilla, W. J. Ramsay,
J. R. Nitschke, Acc. Chem. Res. 2014, 47, 2063-2073.
[12] For self-sorting for self-assembled capsule based on van der Waals and
hydrophobic interactions, see: Y.-Y. Zhan, T. Kojima, K. Ishii, S.
Takahashi, Y. Haketa, H. Maeda, S. Uchiyama, S. Hiraoka, Nature
Commun. 2019, 10, 1440.
[13] For stabilization of very unstable chemical species in covalently bound
capsules, see: R. Warmuth, J. Yoon, Acc. Chem. Res. 2001, 34, 95-105.
[14] For stabilization of reaction intermediates in self-assembled capsules,
see: a) M. Yoshizawa, T. Kusukawa, M. Kawano, T. Ohhara, I. Tanaka,
K. Kurihara, N. Niimura, M. Fujita, J. Am. Chem. Soc. 2005, 127, 2798-
2799; b) D. Fiedler, R. G. Bergman, K. N. Raymond, Angew. Chem. Int.
Ed. 2006, 45, 745-748; Angew. Chem. 2006, 118, 759-762; c) T.
Iwasawa, E. Mann, J. Rebek, Jr., J. Am. Chem. Soc. 2006, 128, 9308-
9309; d) V. M. Dong, D. Fiedler, B. Carl, R. G. Bergman, K. N. Raymond,
J. Am. Chem. Soc. 2006, 128, 14464-14465.
[5]
[6]
[15] For safe storage of hazardous chemicals in self-assembled capsules,
see: a) P. Mal, B. Breiner, K. Rissanen, J. R. Nitschke, Science 2009,
324, 1697-1699; b) M. Yamashina, Y. Sei, M. Akita, M. Yoshizawa,
Nature Commun. 2014, 5, 4662.
For cavitand-based coordination capsules, see: a) F. Fochi, P. Jacopozzi,
E. Wegelius, K. Rissanen, P. Cozzini, E. Marastoni, E. Fisicaro, P. Manini,
R. Fokkens, E. Dalcanale, J. Am. Chem. Soc. 2001, 123, 7539-7552; b)
R. Pinalli, V. Cristini, V. Sottili, S. Geremia, M. Campagnolo, A. Caneschi,
E. Dalcanale, J. Am. Chem. Soc. 2004, 126, 6516-6517; c) K. Kobayashi,
Y. Yamada, M. Yamanaka, Y. Sei, K. Yamaguchi, J. Am. Chem. Soc.
2004, 126, 13896-13897; d) M. Yamanaka, Y. Yamada, Y.; Sei, K.
Yamaguchi, K. Kobayashi, J. Am. Chem. Soc. 2006, 128, 1531-1539; e)
T. Haino, M. Kobayashi, Y. Fukazawa, Chem. Eur. J. 2006, 12, 3310-
3319; f) Y. Tsunoda, K. Fukuta, T. Imamura, R. Sekiya, T. Furuyama, N.
Kobayashi, T. Haino, Angew. Chem. Int. Ed. 2014, 53, 7243-7247;
Angew. Chem. 2014, 126, 7371-7375; g) T. Imamura, T. Maehara, R.
Sekiya, T. Haino, Chem. Eur. J. 2016, 22, 3250-3254; h) L. He, S.-C.
Wang, L.-T. Lin, J.-Y. Cai, L. Li, T.-H. Tu, Y.-T. Chan, J. Am. Chem. Soc.
2020, 142, 7134-7144.
[16] For enhancement of photostability and control over photophysical
properties of organic dyes by encapsulation in self-assembled capsules,
see: a) L. S. Kaanumalle, C. L. D. Gibb, B. C. Gibb, V. Ramamurthy, J.
Am. Chem. Soc. 2005, 127, 3674-3675; b) M. R. Ams, D. Ajami, S. L.
Craig, J.-S. Yang, J. Rebek, Jr., J. Am. Chem. Soc. 2009, 131, 13190-
13191; c) N. Nishimura, K. Kobayashi, J. Org. Chem. 2010, 75, 6079-
6085; d) Y. Hirumi, K. Tamaki, T. Namikawa, K. Kamada, M. Mitsui, K.
Suzuki, K. Kobayashi, Chem. Asian J. 2014, 9, 1282-1290; e) A. M. Raj,
G. Sharma, R. Prabhakar, V. Ramamurthy, Org. Lett. 2019, 21, 5243-
5247.
[17] O. B. Berryman, H. Dube, J. Rebek, Jr., Isr. J. Chem. 2011, 51, 700-709.
[18] For reviews of self-assembled chiral capsules, see: a) M. A. Mateos-
Timoneda, M. Crego-Calama, D. N. Reinhoudt, Chem. Soc. Rev. 2004,
33, 363-372; b) A. Scarso, J. Rebek, Jr., Top. Curr. Chem. 2006, 265, 1-
46; c) G. Seeber, B. E. F. Tiedemann, K. N. Raymond, Top. Curr. Chem.
2006, 265, 147-183.
[7]
[8]
A. Wu, L. Isaacs, J. Am. Chem. Soc. 2003, 125, 4831-4835.
For self-sorting for hydrogen-bonded self-assembled capsules, see: a) D.
Ajami, M. P. Schramm, A. Volonterio, J. Rebek, Jr., Angew. Chem. Int.
Ed. 2007, 46, 242-244; Angew. Chem. 2007, 119, 246-248; b) D. Ajami,
J.-L. Hou, T. J. Dale, E. Barrett, J. Rebek, Jr., Proc. Natl. Acad. Sci. U.S.A.
2009, 106, 10430-10434; c) H. Jedrzejewska, M. Wierzbicki, P. Cmoch,
K. Rissanen, A. Szumna, Angew. Chem. Int. Ed. 2014, 53, 13760-13764;
Angew. Chem. 2014, 126, 13980-13984.
[19] For chiral molecular recognition of racemic guests by using self-
assembled chiral capsules, see: a) R. K. Castellano, B. H. Kim, J. Rebek,
Jr., J. Am. Chem. Soc. 1997, 119, 12671-12672; b) R. K. Castellano, C.
Nuckolls, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 11156-11163; c)
J. M. Rivera, T. Martin, J. Rebek, Jr., J. Am. Chem. Soc. 2001, 123, 5213-
5220; d) D. Fiedler, D. H. Leung, R. G. Bergman, K. N. Raymond, J. Am.
Chem. Soc. 2004, 126, 3674-3675; e) C. J. Hastings, M. D. Pluth, S. M.
Biros, R. G. Bergman, K. N. Raymond, Tetrahedron 2008, 64, 8362-
8367; f) A. Szumna, Chem. Eur. J. 2009, 15, 12381-12388; g) A. U. Malik,
F. Gan, C. Shen, N. Yu, R. Wang, J. Crassous, M. Shu, H. Qiu, J. Am.
Chem. Soc. 2018, 140, 2769-2772.
[9]
For self-sorting for self-assembled capsules based on metal-coordination
bonds, see: a) S. Hiraoka, Y. Kubota, M. Fujita, Chem. Commun. 2000,
1509-1510; b) C. Gütz, R. Hovorka, G. Schnakenburg, A. Lützen, Chem.
Eur. J. 2013, 19, 10890-10894; c) N. Sinha, T. T. Y. Tan, E. Peris, F. E.
Hahn, Angew. Chem. Int. Ed. 2017, 56, 7393-7397; Angew. Chem. 2017,
129, 7499-7503; d) Y.-S. Wang, T. Feng, Y.-Y. Wang, F. E. Hahn, Y.-F.
Han, Angew. Chem. Int. Ed. 2018, 57, 15767-15771; Angew. Chem.
2018, 130, 15993-15997; e) T. Tateishi, T. Kojima, S. Hiraoka, Commun.
Chem. 2018, 1, 20; f) S. Kai, T. Kojima, F. L. Thorp-Greenwood, M. J.
Hardie, S. Hiraoka, Chem. Sci. 2018, 9, 4104-4108; g) T. R. Schulte, J.
J. Holstein, G. H. Clever, Angew. Chem. Int. Ed. 2019, 58, 5562-5566;
Angew. Chem. 2019, 131, 5618-5622; h) F. J.; Rizzuto, J. P. Carpenter,
J. R. Nitschke, J. Am. Chem. Soc. 2019, 141, 9087-9095.; i) D. Bardhan,
[20] A. Ikeda, H. Udzu, Z. Zhong, S. Shinkai, S. Sakamoto, K. Yamaguchi, J.
Am. Chem. Soc. 2001, 123, 3872-3877.
[21] K. Tamaki, A. Ishigami, Y. Tanaka, M. Yamanaka, K. Kobayashi, Chem.
Eur. J. 2015, 21, 13714-13722.
[22] a) Y. Nishioka, T. Yamaguchi, M. Kawano, M. Fujita, J. Am. Chem. Soc.
2008, 130, 8160-8161; b) C. J. Brown, R. G. Bergman, K. N. Raymond,
J. Am. Chem. Soc. 2009, 131, 17530-17531; c) C. Tan, D. Chu, X. Tang,
Y. Liu, W. Xuan, Y. Cui, Chem. Eur. J. 2019, 25, 662-672; d) Y. Fang, J.
A. Powell, E. Li, Q. Wang, Z. Perry, A. Kirchon, X. Yang, Z. Xiao, C. Zhu,
L. Zhang, F. Huang, H.-C. Zhou, Chem. Soc. Rev. 2019, 48, 4707-4730.
12
This article is protected by copyright. All rights reserved.