B. Donnio et al.
M. J. Sienkowska, M. A. Ilies, E. Aqad, J. Smidrkal, P. A. Heiney, J.
Am. Chem. Soc. 2006, 128, 3324–3334.
[15]a) D. J. Pesak, J. S. Moore, Angew. Chem. 1997, 109, 1709–1712;
Angew. Chem. Int. Ed. Engl. 1997, 36, 1636–1639; b) H. Meier, M.
Lehmann, U. Kolb, Chem. Eur. J. 2000, 6, 2462–2469.
[16]a) B. Dardel, D. Guillon, B. Heinrich, R. Deschenaux, J. Mater.
Chem. 2001, 11, 2814–2831; b) S. Campidelli, J. Lenoble, J. Barberµ,
F. Paolucci, M. Marcaccio, D. Paolucci, R. Deschenaux, Macromole-
cules 2005, 38, 7915–7925.
[17]a) V. Percec, P. Chu, G. Ungar, J. Zhou, J. Am. Chem. Soc. 1995,
117, 11441–11454; b) J. L. Li, K. A. Crandall, P. Chu, V. Percec,
R. G. Petschek, C. Rosenblatt, Macromolecules 1996, 29, 7813–
7819.
[18]a) L. Gehringer, D. Guillon, B. Donnio, Macromolecules 2003, 36,
5593–5601; b) L. Gehringer, C. Bourgogne, D. Guillon, B. Donnio,
J. Am. Chem. Soc. 2004, 126, 3856–3867.
[19]J. Barberµ, B. Donnio, L. Gehringer, D. Guillon, M. Marcos, A.
Omenat, J. L. Serrano, J. Mater. Chem. 2005, 15, 4093–4105.
[20]C. J. Hawker, K. L. Wooley, J. M. J. FrØchet, J. Chem. Soc. Perkin
Trans. 1 1993, 1287–1297.
[21]D. J. Pesak, J. S. Moore, Tetrahedron 1997, 53, 15331–15347.
[22]K. Aoi, K. Itoh, M. Okada, Macromolecules 1997, 30, 8072–8074.
[23]a) Y. Pan, W. T. Ford, Macromolecules 1999, 32, 5468–5470; b) Y.
Pan, W. T. Ford, Macromolecules 2000, 33, 3731–3738.
[24]a) T. Imae, M. Ito, K. Aoi, K. Tsutsumiuchi, H. Noda, M. Okada,
Colloids Surf. A 2000, 175, 225–234; b) M. Ito, T. Imae, K. Aoi, K.
Tsutsumiuchi, H. Noda, M. Okada, Langmuir 2002, 18, 9757–9764;
c) K. Tanaka, S. Dai, T. Kajiyama, K. Aoi, M. Okada, Langmuir
2003, 19, 1196–1202.
[37]a) K. Borisch, S. Diele, P. Gçring, H. Kresse, C. Tschierske, Angew.
Chem. 1997, 109, 2188–2190; Angew. Chem. Int. Ed. Engl. 1997, 36,
2087–2089; b) S. Diele, P. Gçring in Handbook of Liquid Crystals,
Vol. 2B (Eds.: D. Demus, J. W. Goodby, G. W. Gray, H. W. Spiess, V.
Vill), Wiley, Weinheim, 1998, pp. 887–900; c) S. D. Hudson, H. T.
Jung, P. Kewsuwan, V. Percec, W. D. Cho, Liq. Cryst. 1999, 26,
1493–1499; d) X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem.
2000, 112, 605–608; Angew. Chem. Int. Ed. 2000, 39, 592–595; e) S.
Diele, Curr. Opin. Colloid Interface Sci. 2002, 7, 333–342; f) T.
Kato, T. Matsuoka, M. Nishii, K. Kamikawa, K. Kanie, T. Nishi-
mura, E. Yashima, S. Ujiie, Angew. Chem. 2004, 116, 2003–2006;
Angew. Chem. Int. Ed. 2004, 43, 1969–1972; g) B. K. Cho, A. Jain,
S. M. Gruner, U. Wiesner, Science 2004, 305, 1598–1601.
[38]This compound was reported to exhibit an additional mesophase,
¯
which was not detected in our case (Cr 63 Colh 64 Cub-Pm3n 87 I):
K. Borisch, S. Diele, P. Gçring, H. Kresse, C. Tschierske, J. Mater.
Chem. 1998, 8, 529–543. However, it appeared that the occurrence
of the cubic mesophase and the transition temperatures strongly
depend on contamination by small amounts of water. Thus, the
phase sequence of the completely dried sample is Cr 48 Colh 65
¯
Cub-Pm3n 78 I, whereas, after the work-up procedure, the phase se-
quence is similar to ours reported here, that is, Cr 62 Colh 75 I: R.
Dunkel, M. Hahn, K. Borisch, B. Neumann, H. H. Rüttinger, C.
Tschierske, Liq. Cryst. 1998, 24, 211–213.
[39]a) K. Borisch, S. Diele, P. Gçring, H. Müller, C. Tschierske, Liq.
Cryst. 1997, 22, 427–443; b) K. Borisch, S. Diele, P. Gçring, H.
Kresse, C. Tschierske, J. Mater. Chem. 1998, 8, 529–543; c) A. Pege-
nau, T. Hegmann, C. Tschierske, S. Diele, Chem. Eur. J. 1999, 5,
1643–1660.
[40]J. M. Seddon, Biochim. Biophys. Acta 1990, 1031, 1–69.
[41]a) H. Ringsdorf, B. Schlarb, J. Venzmer, Angew. Chem. 1988, 100,
117–162; Angew. Chem. Int. Ed. Engl. 1988, 27, 113–158; b) C.
Tschierske, Prog. Polym. Sci. 1996, 21, 775–852.
[42]a) K. Borisch, C. Tschierske, P. Gçring, S. Diele, Chem. Commun.
1998, 2711–2712; b) S. Fischer, H. Fischer, S. Diele, G. Pelzl, K. Jan-
kowski, R. R. Schmidt, V. Vill, Liq. Cryst. 1994, 17, 855–861.
[43]a) J. M. Seddon, R. H. Templer, Philos. Trans. R. Soc. London Ser. A
1993, 344, 377–401; b) J. M. Seddon, R. H. Templer in Handbook of
Biological Physics, Vol. 1 (Eds.: R. Lipowsky, E. Sackmann), Elsevi-
er, Leiden, The Netherlands, 1995, pp. 97–160.
[44]a) S. Kutsumizu, Curr. Opin. Colloid Interface Sci. 2002, 7, 537–543;
b) M. ImpØror-Clerc, Curr. Opin. Chem. Biol. 2005, 9, 370–376.
[45]a) A. Tardieu, V. Luzzati, Biochim. Biophys. Acta 1970, 219, 11;
b) K. Fontel, K. K. Fox, E. Hanson, Mol. Cryst. Liq. Cryst. Lett.
1985, 1, 9.
[46]a) R. Vargas, P. Mariani, A. Gulik, V. Luzzati, J. Mol. Biol. 1992,
225, 137–145; b) V. Luzzati, R. Vargas, P. Mariani, A. Gulik, H. De-
lacroix, J. Mol. Biol. 1993, 229, 540–551; c) A. Gulik, H. Delacroix,
G. Kirschner, V. Luzzati, J. Phys. II 1995, 5, 445–464; d) V. Luzzati,
J. Phys. II 1995, 5, 1649–1669.
[47]G. Hꢁgg, N. Schçnberg, Acta Crystallogr. 1954, 7, 351–352.
[48]M. R. Fitzsimmons, J. A. Eastment, R. A. Robinson, A. C. Lawson,
J. D. Thompson, R. Movshovitch, J. Satti, Phys. Rev. B 1993, 48,
8245–8252.
[49]M. OꢂKeeffe, Acta Crystallogr. Sect. A 1998, 54, 320–329.
[50]a) D. Weaire, R. Phelan, Philos. Mag. Lett. 1994, 69, 107–110; b) D.
Weaire, The Kelvin Problem, Taylor & Francis, London, 1996; c) T.
Aste, D. Weaire, The Pursuit of Perfect Packing, Institute of Physics
Publishing, Bristol and Philadelphia, 2000; d) A. Bçlcskei, Period.
Polytech. Mech. Eng. 2003, 47, 15–23.
[51]a) J.-F. Sadoc, N. Rivier, Foams and Emulsions, Kluwer, Dordrecht,
The Netherlands, 1999; b) S. Hilgenfeldt, Nieuw Archief voor Wis-
kunde, 2002, 5, 224–230.
[25]a) J. Ropponen, S. Nummelin, K. Rissanen, Org. Lett. 2004, 6, 2495–
2497; b) N. R. Luman, M. W. Grinstaff, Org. Lett. 2005, 7, 4863–
4866; c) H.-F. Chow, K.-F. Ng, Z.-Y. Wang, C.-H. Wong, T. Luk, C.-
M. Lo, Y.-Y. Yang, Org. Lett. 2006, 8, 471–474.
[26]a) I. M. Saez, J. W. Goodby, J. Mater. Chem. 2005, 15, 26–40; b) V.
Percec, M. R. Imam, T. K. Bera, V. S. K. Balagurusamy, M. Peterca,
P. A. Heiney, Angew. Chem. 2005, 117, 6674–6679; Angew. Chem.
Int. Ed. 2005, 44, 4739–4745.
[27]G. Ungar, X. Zeng, Soft Matter 2005, 1, 95–106.
[28]a) J. Kohda, K. Shinozuka, H. Sawai, Tetrahedron Lett. 1995, 36,
5575–5578; b) F. Caturla, J. Enjo, M. C. Bernabeu, S. Le Serre, Tet-
rahedron 2004, 60, 1903–1911; c) F. Otis, N. Voyer, A. Polidori, B.
Pucci, New J. Chem. 2006, 30, 185–190.
[29]M. Ueda, A. Kameyama, K. Hashimoto, Macromolecules 1988, 21,
19–24.
[30]a) R. M. Nouguier, M. Mchich, J. Org. Chem. 1985, 50, 3296–3298;
b) R. M. Nouguier, M. Mchich, J. Org. Chem. 1987, 52, 2995–2997.
[31]O. Mitsunobu, Synthesis 1981, 1–28.
[32]J. MalthÞte, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171–
187.
[33]a) P. Sotta, J. Phys. II 1991, 1, 763–772; b) P. Sakya, J. M. Seddon,
R. H. Templer, J. Phys. II 1994, 4, 1311–1331; c) M. ImpØror-Clerc,
M. Veber, A. M. Levelut, ChemPhysChem 2001, 2, 533–535.
[34]In lyotropic systems, the following convention is used and has been
kept here: mesophases with a normal topology, for example, oil-in-
water phases are said to possess a positive curvature with the polar
parts pointing outwards and the apolar parts inwards, in contrast to
inverted mesophases (opposite topology for example, water-in-oil
phases), which thus have a negative curvature.
[35]a) R. Vargas, P. Mariani, A. Gulik, V. Luzzati, J. Mol. Biol. 1992,
225, 137–145; b) H. Delacroix, T. Gulik-Krzywicki, P. Mariani V.
Luzzati, J. Mol. Biol. 1993, 229, 526–539; c) T. Gulik-Krzywicki, H.
Delacroix, Biol. Cell 1994, 80, 193–201; d) A. Gulik, H. Delacroix,
G. Kirschner, V. Luzzati, J. Phys. II 1995, 5, 445–464; e) M. Clerc, J.
Phys. II 1996, 6, 961–968.
[36]a) K. Fontell, Colloid Polym. Sci. 1990, 268, 264–295; b) S. T. Hyde
in Handbook of Applied Surface and Colloid Chemistry (Ed.: K.
Holmberg), Wiley, 2001, pp. 299–322; c) P. Sakya, J. M. Seddon,
R. H. Templer, R. J. Mirkin, G. J. T. Tiddy, Langmuir 1997, 13,
3706–3714.
[52]A. K. van der Vegt, “Order in space”, to be found under http://
[53]J. Charvolin, Contemp. Phys. 1990, 31, 1–17.
[54]J. Charvolin, J.-F. Sadoc, J. Phys. 1988, 49, 521–526.
8412
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2006, 12, 8396 – 8413