Cucurbit[6]uril dimer induces supramolecular polymerisation of a cationic polyethylene glycol derivative

References

• Day, A.I.; Arnold, A.P.; Blanch, R.J.; Snushall, B. J. Org. Chem.2001, 66, 8094–8100; Day, A.I.; Blanch, R.J.; Arnold, A.P.; Lorenzo, S.; Lewis, G.R.; Dance, I. Angew. Chem., Int. Ed.2002, 41, 275–277; Freeman, W.A.; Mock, W.L.; Shih, N.-Y. J. Am. Chem. Soc.1981, 103, 7367–7368; Liu, S.; Zavalij, P.Y.; Isaacs, L. J. Am. Chem. Soc.2005, 127, 16798–16799.
   Google Scholar
• Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K.J. Am. Chem. Soc.2000, 122, 540–541.
   Web of Science ®Google Scholar
• Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed.2005, 44, 4844–4870; Lee, J.W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res.2003, 36, 621–630; Masson, E.; Ling, X.; Joseph, R.; Kyeremeh-Mensah, L.; Lu, X. RSC Adv.2012, 2, 1213–1247.
   Google Scholar
• Nau, W.M.; Florea, M.; Assaf, K.I.Isr. J. Chem.2011, 51, 559–577.
   Web of Science ®Google Scholar
• Rekharsky, M.; Inoue, Y. Chem. Rev.1998, 98, 1875–1917; Diederich, F. Angew. Chem., Int. Ed. Engl.1988, 27, 362–386; Cram, D.J. Angew. Chem., Int. Ed. Engl.1988, 27, 1009–1020; Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: New York, 1995.
   Google Scholar
• Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P.Y.; Isaacs, L. J. Am. Chem. Soc.2005, 127, 15959–15967; Rekharsky, M.V.; Mori, T.; Yang, C.; Ko, Y.H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A.E.; Liu, S.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M.K.; Kim, K.; Inoue, Y. Proc. Natl. Acad. Sci. USA2007, 104, 20737–20742; Biedermann, F.; Uzunova, V.D.; Scherman, O.A.; Nau, W.M.; De Simone, A. J. Am. Chem. Soc.2012, 134, 15318–15323; Moghaddam, S.; Yang, C.; Rekharsky, M.; Ko, Y.H.; Kim, K.; Inoue, Y.; Gilson, M.K. J. Am. Chem. Soc.2011, 133, 3570–3581; Florea, M.; Nau, W.M. Angew. Chem., Int. Ed.2011, 50, 9338–9342.
   Google Scholar
• Mock, W.L.; Shih, N.Y.J. Org. Chem.1986, 51, 4440–4446.
   Web of Science ®Google Scholar
• Ghosh, I.; Nau, W. M. Adv. Drug Delivery Rev.2012, 64, 764–783; Mock, W.L.; Pierpont, J. J. Chem. Soc., Chem. Commun.1990, 1509–1511.
   Google Scholar
• Marquez, C.; Nau, W.M.Angew. Chem., Int. Ed.2001, 40, 4387–4390.
   PubMed Web of Science ®Google Scholar
• Hennig, A.; Bakirci, H.; Nau, W.M. Nat. Methods2007, 4, 629–632; Wu, J.; Isaacs, L. Chem. Eur. J.2009, 15, 11675–11680; Biedermann, F.; Rauwald, U.; Cziferszky, M.; Williams, K.A.; Gann, L.D.; Guo, B.Y.; Urbach, A.R.; Bielawski, C.W.; Scherman, O.A. Chem. Eur. J.2010, 16, 13716–13722; Ghale, G.; Ramalingam, V.; Urbach, A.R.; Nau, W.M. J. Am. Chem. Soc.2011, 133, 7528–7535; Dsouza, R.N.; Pischel, U.; Nau, W.M. Chem. Rev.2011, 111, 7941–7980.
   Google Scholar
• Jung, H.; Park, K.M.; Yang, J.-A.; Oh, E.J.; Lee, D.-W.; Park, K.; Ryu, S.H.; Hahn, S.K.; Kim, K. Biomaterials2011, 32, 7687–7694; Kim, C.; Agasti, S.S.; Zhu, Z.; Isaacs, L.; Rotello, V.M. Nat. Chem.2010, 2, 962–966; Park, K.M.; Lee, D.-W.; Sarkar, B.; Jung, H.; Kim, J.; Ko, Y.H.; Lee, K.E.; Jeon, H.; Kim, K. Small2010, 6, 1430–1441; Hettiarachchi, G.; Nguyen, D.; Wu, J.; Lucas, D.; Ma, D.; Isaacs, L.; Briken, V. PLoS One2010, 5, e10514; Wheate, N.J.; Buck, D.P.; Day, A.I.; Collins, J.G. Dalton Trans.2006, 451–458; Zhao, Y.; Buck, D.P.; Morris, D.L.; Pourgholami, M.H.; Day, A.I.; Collins, J.G. Org. Biomol. Chem.2008, 6, 4509–4515; Uzunova, V.D.; Cullinane, C.; Brix, K.; Nau, W.M.; Day, A.I. Org. Biomol. Chem.2010, 8, 2037–2042; Walker, S.; Oun, R.; McInnes, F.J.; Wheate, N.J. Isr. J. Chem.2011, 51, 616–624; Dong, N.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.; Zhao, Y.; Yang, L.-X. Supramol. Chem.2008, 20, 659–665; Loh, X.J.; del Barrio, J.; Toh, P.P.C.; Lee, T.-C.; Jiao, D.; Rauwald, U.; Appel, E.A.; Scherman, O.A. Biomacromolecules2012, 13, 84–91; Appel, E.A.; Rowland, M.J.; Loh, X.J.; Heywood, R.M.; Watts, C.; Scherman, O.A. Chem. Commun.2012, 48, 9843–9845; Park, K.M.; Suh, K.; Jung, H.; Lee, D.-W.; Ahn, Y.; Kim, J.; Baek, K.; Kim, K. Chem. Commun.2009, 71–73; Jeon, Y.J.; Kim, S.-Y.; Ko, Y.H.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Org. Biomol. Chem.2005, 3, 2122–2125; Saleh, N.; Meetani, M.A.; Al-Kaabi, L.; Ghosh, I.; Nau, W.M. Supramol. Chem.2011, 23, 654–661.
   Google Scholar
• Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J.B.; Zavalij, P.Y.; Briken, V.; Isaacs, L.Nat. Chem.2012, 4, 503–510.
   PubMed Web of Science ®Google Scholar
• Zhang, J.; Coulston, R.J.; Jones, S.T.; Geng, J.; Scherman, O.A.; Abell, C.Science2012, 335, 690–694.
   PubMed Web of Science ®Google Scholar
• Ma, D.; Zhang, B.; Hoffmann, U.; Sundrup, M.G.; Eikermann, M.; Isaacs, L.Angew. Chem., Int. Ed.2012, 51, 11358–11362.
   PubMed Web of Science ®Google Scholar
• Ko, Y.H.; Kim, E.; Hwang, I.; Kim, K. Chem. Commun.2007, 1305–1315; Tian, F.; Jiao, D.; Biedermann, F.; Scherman, O.A. Nat. Commun.2012, 3, 2198/1–2198/8.
   Google Scholar
• Baek, K.; Yun, G.; Kim, Y.; Kim, D.; Hota, R.; Hwang, I.; Xu, D.; Ko, Y.H.; Gu, G.H.; Suh, J.H.; Park, C.G.; Sung, B.J.; Kim, K. J. Am. Chem. Soc.2013, 135, 6523–6528; Park, K.M.; Yang, J.-A.; Jung, H.; Yeom, J.; Park, J.S.; Park, K.-H.; Hoffman, A.S.; Hahn, S.K.; Kim, K. ACS Nano2012, 6, 2960–2968; Appel, E.A.; Biedermann, F.; Rauwald, U.; Jones, S.T.; Zayed, J.M.; Scherman, O.A. J. Am. Chem. Soc.2010, 132, 14251–14260; Jiao, D.; Geng, J.; Loh, X.J.; Das, D.; Lee, T.-C.; Scherman, O.A. Angew. Chem., Int. Ed.2012, 51, 9633–9637.
   Google Scholar
• Rauwald, U.; Scherman, O.A.Angew. Chem., Int. Ed.2008, 47, 3950–3953.
   PubMed Web of Science ®Google Scholar
• Appel, E.A.; Dyson, J.; del Barrio, J.; Walsh, Z.; Scherman, O.A. Angew. Chem., Int. Ed.2012, 51, 4185–4189; Appel, E.A.; Loh, X.J.; Jones, S.T.; Biedermann, F.; Dreiss, C.A.; Scherman, O.A. J. Am. Chem. Soc.2012, 134, 11767–11773; Kasera, S.; Biedermann, F.; Baumberg, J.J.; Scherman, O.A.; Mahajan, S. Nano Lett.2012, 12, 5924–5928.
   Google Scholar
• Lee, T.-C.; Kalenius, E.; Lazar, A.I.; Assaf, K.I.; Kuhnert, N.; Gruen, C.H.; Jaenis, J.; Scherman, O.A.; Nau, W.M. Nat. Chem.2013, 5, 376–382; Kloeck, C.; Dsouza, R.N.; Nau, W.M. Org. Lett.2009, 11, 2595–2598; Lu, X.; Masson, E. Org. Lett.2010, 12, 2310–2313; Pemberton, B.C.; Singh, R.K.; Johnson, A.C.; Jockusch, S.; Da Silva, J.P.; Ugrinov, A.; Turro, N.J.; Srivastava, D.K.; Sivaguru, J. Chem. Commun.2011, 47, 6323–6325; Jon, S.Y.; Ko, Y.H.; Park, S.H.; Kim, H.-J.; Kim, K. Chem. Commun.2001, 1938–1939; Mock, W.L.; Irra, T.A.; Wepsiec, J.P.; Adhya, M. J. Org. Chem.1989, 54, 5302–5308.
   Google Scholar
• El-Sheshtawy, H.S.; Bassil, B.S.; Assaf, K.I.; Kortz, U.; Nau, W.M. J. Am. Chem. Soc.2012, 134, 19935–19941; Biedermann, F.; Rauwald, U.; Zayed, J.M.; Scherman, O.A. Chem. Sci.2011, 2, 279–286; Liu, S.; Zavalij, P.Y.; Lam, Y.-F.; Isaacs, L. J. Am. Chem. Soc.2007, 129, 11232–11241; Liu, S.; Shukla, A.D.; Gadde, S.; Wagner, B.D.; Kaifer, A.E.; Isaacs, L. Angew. Chem., Int. Ed.2008, 47, 2657–2660; Ghosh, S.; Isaacs, L. J. Am. Chem. Soc.2010, 132, 4445–4454.
   Google Scholar
• Lee, D.-W.; Park, K.M.; Banerjee, M.; Ha, S.H.; Lee, T.; Suh, K.; Paul, S.; Jung, H.; Kim, J.; Selvapalam, N.; Ryu, S.H.; Kim, K.Nat. Chem.2011, 3, 154–159.
   PubMed Web of Science ®Google Scholar
• Ahn, Y.; Jang, Y.; Selvapalam, N.; Yun, G.; Kim, K.Angew. Chem., Int. Ed.2013, 52, 3140–3144.
   PubMed Web of Science ®Google Scholar
• Isaacs, L.; Park, S.-K.; Liu, S.; Ko, Y.H.; Selvapalam, N.; Kim, Y.; Kim, H.; Zavalij, P. Y.; Kim, G.-H.; Lee, H.-S.; Kim, K. J. Am. Chem. Soc.2005, 127, 18000–18001; Liu, S.; Kim, K.; Isaacs, L. J. Org. Chem.2007, 72, 6840–6847.
   Google Scholar
• Lagona, J.; Fettinger, J.C.; Isaacs, L. Org. Lett.2003, 5, 3745–3747; Lagona, J.; Fettinger, J.C.; Isaacs, L. J. Org. Chem.2005, 70, 10381–10392; Wagner, B.D.; Boland, P.G.; Lagona, J.; Isaacs, L. J. Phys. Chem. B2005, 109, 7686–7691.
   Google Scholar
• Huang, W.-H.; Liu, S.; Zavalij, P.Y.; Isaacs, L.J. Am. Chem. Soc.2006, 128, 14744–14745.
   PubMed Web of Science ®Google Scholar
• Huang, W.-H.; Zavalij, P.Y.; Isaacs, L. Angew. Chem., Int. Ed.2007, 46, 7425–7427; Huang, W.-H.; Zavalij, P.Y.; Isaacs, L. Org. Lett.2008, 10, 2577–2580.
   Google Scholar
• Huang, W.-H.; Zavalij, P.Y.; Isaacs, L. Org. Lett.2009, 11, 3918–3921; Lucas, D.; Isaacs, L. Org. Lett.2011, 13, 4112–4115.
   Google Scholar
• Minami, T.; Esipenko, N.A.; Zhang, B.; Isaacs, L.; Nishiyabu, R.; Kubo, Y.; Anzenbacher, P. J. Am. Chem. Soc.2012, 134, 20021–20024; Shen, C.; Ma, D.; Meany, B.; Isaacs, L.; Wang, Y. J. Am. Chem. Soc.2012, 134, 7254–7257.
   Google Scholar
• Lucas, D.; Minami, T.; Iannuzzi, G.; Cao, L.; Wittenberg, J.B.; Anzenbacher, P.J.; Isaacs, L.J. Am. Chem. Soc.2011, 133, 17966–17976.
   PubMed Web of Science ®Google Scholar
• Cao, L.; Isaacs, L.Org. Lett.2012, 14, 3072–3075.
   PubMed Web of Science ®Google Scholar
• Vinciguerra, B.; Cao, L.; Cannon, J.R.; Zavalij, P.Y.; Fenselau, C.; Isaacs, L.J. Am. Chem. Soc.2012, 134, 13133–13140.
   PubMed Web of Science ®Google Scholar
• Wittenberg, J.B.; Zavalij, P.Y.; Isaacs, L.Angew. Chem. Int. Ed.2013, 52, 3690–3694.
   PubMed Web of Science ®Google Scholar
• Wittenberg, J.B.; Costales, M.G.; Zavalij, P.Y.; Isaacs, L.Chem. Commun.2011, 47, 9420–9422.
   PubMed Web of Science ®Google Scholar
• Michelsen, U.; Hunter, C.A. Angew. Chem., Int. Ed.2000, 39, 764–767; Velten, U.; Rehahn, M.G.S. Chem. Commun.1996, 2639–2640; Hofmeier, H.; Hoogenboom, R.; Wouters, M.E.; Schubert, U.S. J. Am. Chem. Soc.2005, 127, 2913–2921.
   Google Scholar
• Simic, V.; Bouteiller, L.; Jalabert, M. J. Am. Chem. Soc.2003, 125, 13148–13154; Beck, J.B.; Rowan, S.J. J. Am. Chem. Soc.2003, 125, 13922–13923; Bladon, P.; Griffin, A.C. Macromolecules1993, 26, 6604–6610; Gulik-Krzywicki, T.; Fouquey, C.; Lehn, J.M. Proc. Natl. Acad. Sci. USA1993, 90, 163–167.
   Google Scholar
• Sijbesma, R.P.; Beijer, F.H.; Brunsveld, L.; Folmer, B.J.; Hirschberg, J.H.; Lange, R.F.; Lowe, J.K.; Meijer, E.W.Science1997, 278, 1601–1604.
   PubMed Web of Science ®Google Scholar
• Gabriel, G.J.; Sorey, S.; Iverson, B.L. J. Am. Chem. Soc.2005, 127, 2637–2640; Markovitsi, D.; Bengs, H.; Ringsdorf, H. J. Chem. Soc., Faraday Trans.1992, 88, 1275–1279.
   Google Scholar
• Miyawaki, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Tetrahedron2008, 64, 8355–8361; Castellano, R.K.; Rudkevich, D.M.; Rebek, J. Proc. Natl. Acad. Sci. USA1997, 94, 7132–7137; Skene, W.G.; Lehn, J.-M. P. Proc. Natl. Acad. Sci. USA2004, 101, 8270–8275; Dong, S.; Yan, X.; Zheng, B.; Chen, J.; Ding, X.; Yu, Y.; Xu, D.; Zhang, M.; Huang, F. Chem. Eur. J.2012, 18, 4195–4199; Ji, X.; Yao, Y.; Li, J.; Yan, X.; Huang, F. J. Am. Chem. Soc.2013, 135, 74–77; Niu, Z.; Huang, F.; Gibson, H.W. J. Am. Chem. Soc.2011, 133, 2836–2839.
   Google Scholar
• Miyauchi, M.; Harada, A.J. Am. Chem. Soc.2004, 126, 11418–11419.
   PubMed Web of Science ®Google Scholar
• Kim, H.-J.; Heo, J.; Jeon, W.S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K.Angew. Chem., Int. Ed.2001, 40, 1526–1529.
   PubMed Web of Science ®Google Scholar
• Ko, Y.H.; Kim, K.; Kang, J.K.; Chun, H.; Lee, J.W.; Sakamoto, S.; Yamaguchi, K.; Fettinger, J.C.; Kim, K. J. Am. Chem. Soc.2004, 126, 1932–1933; Kim, S.-Y.; Ko, Y.H.; Lee, J.W.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Chem. Asian J.2007, 2, 747–754.
   Google Scholar
• Liu, Y.; Yu, Y.; Gao, J.; Wang, Z.; Zhang, X. Angew. Chem., Int. Ed.2010, 49, 6576–6579; Liu, Y.-L.; Liu, K.; Wang, Z.-Q.; Zhang, X. Chem. – Eur. J.2011, 17, 9930–9935.
   Google Scholar
• Nally, R.; Isaacs, L.Tetrahedron2009, 65, 7249–7258.
   Web of Science ®Google Scholar
• Nally, R.; Scherman, O.A.; Isaacs, L. Supramol. Chem.2010, 22, 683–690; Appel, E.A.; Barrio, J.D.; Dyson, J.; Isaacs, L.; Scherman, O.A. Chem. Sci.2012, 3, 2278–2281.
   Google Scholar
• Cohen, Y.; Avram, L.; Frisch, L. Angew. Chem., Int. Ed.2005, 44, 520–554; Stejskal, E.O.; Tanner, J.E. J. Chem. Phys.1965, 42, 288–292.
   Google Scholar
• Zhu, P.; Yang, H.; Peng, C.; Zhang, X. Macromol. Chem. Phys.2001, 202, 1380–1383; Ho, D.L.; Hammouda, B.; Kline, S.R. J. Polym. Sci. Part B: Polym. Phys.2002, 41, 135–138; Linegar, K.L.; Adeniran, A.E.; Kostko, A.F.; Anisimov, M.A. Colloid J.2010, 72, 279–281.
   Google Scholar
• Shimada, K.; Kato, H.; Saito, T.; Matsuyama, S.; Kinugasa, S.J. Chem. Phys.2005, 122, 244914.
   PubMed Web of Science ®Google Scholar
• Brunsveld, L.; Folmer, B.J.; Meijer, E.W.; Sijbesma, R.P.Chem. Rev.2001, 101, 4071–4098.
   PubMed Web of Science ®Google Scholar
• Marquez, C.; Nau, W.M. Angew. Chem., Int. Ed. 2001, 40, 3155–3160; Marquez, C.; Hudgins, R.R.; Nau, W.M. J. Am. Chem. Soc.2004, 126, 5808–5816; Mock, W.L.; Shih, N.-Y. J. Am. Chem. Soc.1989, 111, 2697–2699.
   Google Scholar
• Arduini, A.; Bussolati, R.; Credi, A.; Faimani, G.; Garaudee, S.; Pochini, A.; Secchi, A.; Semeraro, M.; Silvi, S.; Venturi, M.Chem. Eur. J.2009, 15, 3230–3242.
   PubMed Web of Science ®Google Scholar
• Jiang, W.; Schalley, C.A.Beilstein J. Org. Chem.2010, 6, 14.
   PubMed Web of Science ®Google Scholar