Paraquat guest-induced conformational templation of dicarboxylatocalixarenes

References

• Gutsche , C.D. 2008 . Calixarenes, An Introduction , Cambridge, UK : Royal Society of Chemistry .
   Google Scholar
• For a review on self-assembly in solution, see: (a) Rudkevich, D.M. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001; pp 155–180. For a review on solid-state self-assembly, see: (b) Dalgarno, S.J.; Thallapally, P.K.; Barbour, L.J.; Atwood, J.L. Chem. Soc. Rev. 2007, 36, 236–245. (c) Gaeta, C.; Tedesco, C.; Neri, P. In Calixarenes in the Nanoworld; Vicens, J., Harrowfield, J., Eds.; Springer: Dordrecht, 2006; Chapter 16, pp 335–354
   Google Scholar
• Beer , P.D. and Gale , P.A. 2001 . Angew. Chem. Int. Ed. , 40 : 486 – 516 .
   PubMed Web of Science ®Google Scholar
• (a) Homden, D.M.; Redshaw, C. Chem. Rev. 2008, 108, 5086–5130. (b) Kovbasyuk, L.; Krämer, R. Chem. Rev. 2004, 104, 3161–3188
   Google Scholar
• Vicens , J. and Harrowfield , J. , eds. 2006 . Calixarenes in the Nanoworld , Dordrecht : Springer .
   Google Scholar
• (a) Ménand, M.; Leroy, A.; Marrot, J.; Luhmer, M.; Jabin, I. Angew. Chem. Int. Ed. 2009, 48, 5509–5512. (b) Coquière, D.; de la Lande, A.; Martì, S.; Parisel, O.; Prangé, T.; Reinaud, O. Proc. Natl Acad. Sci. USA 2009, 106, 10449–10454 and references therein. (c) Cacciapaglia, R.; Casnati, A.; Mandolini, L.; Reinhoudt, D.N.; Salvio, R.; Sartori, A.; Ungaro, R. J. Org. Chem. 2005, 70, 624–630. (d) Molenveld, P.; Engbersen, J.F.J.; Reinhoudt, D.N. Chem. Soc. Rev. 2000, 29, 75–86
   Google Scholar
• (a) Specht, A.; Bernard, P.; Goeldner, M.; Peng, L. Angew. Chem., Int. Ed. 2002, 41, 4706–4708. (b) Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.-F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1506–1509
   Google Scholar
• (a) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett. 1993, 205–208. (b) For a general review with a focus on cation recognition and templation, see: Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713–1734
   Google Scholar
• (a) Gaeta, C.; Martino, M.; Neri, P. Org. Lett. 2006, 8, 4409–4412. (b) Consoli, G.M.L.; Cunsolo, F.; Geraci, C.; Gavuzzo, E.; Neri, P. Tetrahedron Lett. 2002, 43, 1209–1211. (c) Consoli, G.M.L.; Cunsolo, F.; Geraci, C.; Neri, P. Org. Lett. 2001, 3, 1605–1608
   Google Scholar
• (a) Dalgarno, S.J.; Warren, J.E.; Antesberger, J.; Glass, T.E.; Atwood, J.L. New J. Chem. 2007, 31, 1891–1894. (b) Kennedy, S.; Karotsis, G.; Beavers, C.M.; Teat, S.J.; Brechin, E.K.; Dalgarno, S.J. Angew. Chem. Int. Ed. 2010, 49, 4205–4208
   Google Scholar
• Pierro , T. , Gaeta , C. , Troisi , F. and Neri , P. 2009 . Tetrahedron Lett. , 50 : 350 – 353 .
   Web of Science ®Google Scholar
• Arduini , A. , Casnati , A. , Dodi , L. , Pochini , A. and Ungaro , R. 1990 . J. Chem. Soc., Chem. Commun. , : 1597 – 1598 .
   Google Scholar
• Larsen , M. and Jørgensen , M. 1996 . J. Org. Chem. , 61 : 6651 – 6655 .
   PubMed Web of Science ®Google Scholar
• It is well known that tetramethoxycalix[4]arene derivatives are flexible systems freely interconverting between four conformations. In fact, the interconversion among the four possible calix[4]arene conformations (cone, partial-cone, 1,2- and 1,3-alternate) is only impeded when substituents larger than ethyl group are attached at the phenolic OH groups (Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4955–4962)
   Google Scholar
• Macromodel Version 9.0, Schrödinger, LLC, New York, NY, 2005; Mohamadi, F.; Richards, N.G.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440–467
   Google Scholar
• (a) Connors, K.A. Binding Constants; Wiley: Chichester, 1987. (b) Fielding, L. Tetrahedron 2000, 56, 6151–6170. (c) Hirose, K. J. Incl. Phenom. Macrocycl. Chem. 2001, 39, 193–209. (c) Hynes, M.J. J. Chem. Soc., Dalton Trans. 1993, 311–312
   Google Scholar
• Withlock , B.J. and Withlock , H.W. 1990 . J. Am. Chem. Soc. , 112 : 3910 – 3915 .
   Web of Science ®Google Scholar
• For recent examples of pH-depending threading/dethreading of calixarene pseudorotaxanes, see: (a) Silvi, S.; Arduini, A.; Pochini, A.; Secchi, A.; Tomasulo, M.; Raymo, F.M.; Baroncini, M.; Credi, A. J. Am. Chem. Soc. 2007, 129, 13378–13379. (b) Gattuso, G.; Notti, A.; Parisi, M.F.; Pisagatti, I.; Amato, M.E.; Pappalardo, A.; Pappalardo, S. Chem. Eur. J. 2010, 16, 2381–2385. (c) Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092–2095
   Google Scholar
• For reviews on molecular switches, see: (a) de Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Chem. Rev. 1997, 97, 1515–1566. (b) Feringa, B.L., Ed.; Molecular Switches; Wiley-VCH: Weinheim, 2001. (c) Szaciłowski, K. Chem. Rev. 2008, 108, 3481–3548
   Google Scholar
• Kanamathareddy , S. and Gutsche , C.D. 1992 . J. Org. Chem. , 57 : 3160 – 3166 .
   Web of Science ®Google Scholar
• Gutsche , C.D. 1989 . Calixarenes , 110 – 111 . Cambridge : Royal Society of Chemistry .
   Google Scholar
• (a) Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P.M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372–3376. (b) Magrans, J.O.; de Mendoza, J.; Pons, M.; Prados, P. J. Org. Chem. 1997, 62, 4518–4520
   Google Scholar
• (a) Bifulco, G.; Gomez-Paloma, L.; Riccio, R.; Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2005, 7, 5757–5760. (b) Bifulco, G.; Riccio, R.; Gaeta, C.; Neri, P. Chem. Eur. J. 2007, 13, 7185–7194
   Google Scholar
• Arduini , A. , Ferdani , R. , Pochini , A. , Secchi , A. and Ugozzoli , F. 2000 . Angew. Chem. Int. Ed. , 39 : 3453 – 3456 .
   PubMed Web of Science ®Google Scholar