Paper
Soft Matter
diluted with 10 ml water and acidied by the addition of 10 ml
conc. HCl. The mixture was kept at ꢁ20 ꢀC for 20 min, and the
precipitate was ltered off, washed with ice/water and dried.
5-Decyl-barbituric acid 3a (ref. 49) Yield: 82% (1.47 g),
3 (a) C. M. Paleos and D. Tsiourvas, Liq. Cryst., 2001, 28, 1127;
(b) T. Kato, Struct. Bonding, 2000, 96, 95; (c) T. Kato, in
Handbook of Liquid Crystals, ed. D. Demus, J. W. Goodby,
G. W. Gray, H.-W. Spiess and V. Vill, Wiley-VCH,
Weinheim, Germany, 1998, vol. 2B, pp. 969–978.
C
14H24N2O3 (268.18). MS m/z: 268 (M+).
IR n ¼ 3232, 3071, 2916, 2847, 1705, 1566, 1512, 1465, 1303,
4 D. Janietz and A. Kohlmeier, Liq. Cryst., 2009, 36, 685.
5 (a) T. Kato and J. M. J. Frechet, J. Am. Chem. Soc., 1989, 111,
8533; (b) T. Kato, J. M. J. Frechet, P. G. Wilson, T. Saito,
T. Uryu, A. Fujishima, C. Jin and F. Kaneuchi, Chem.
Mater., 1993, 5, 1094; (c) T. Kato, M. Fukumasa and
J. M. J. Frechet, Chem. Mater., 1995, 7, 368.
6 (a) T. Kato, Y. Kubota, M. Nakano and T. Uryu, Chem. Lett.,
1995, 1127; (b) T. Kato, M. Nakano, T. Moteki, T. Uryu and
S. Ujiie, Macromolecules, 1995, 28, 8875.
7 (a) M.-J. Brienne, J. Gabard, J.-M. Lehn and I. Stibor, J. Chem.
Soc., Chem. Commun., 1989, 1868; (b) C. Fouquey, J.-M. Lehn
and A.-M. Levelut, Adv. Mater., 1990, 2, 254.
8 D. Goldmann, R. Dietel, D. Janietz, C. Schmidt and
J. H. Wendorff, Liq. Cryst., 1998, 24, 407.
1265, 918 cmꢁ1
.
1H-NMR (DMSO-d6): d ¼ 12.6 (s, 2H, NH), 3.2 (t, 1H, CH, J ¼
7.4 Hz), 1.7 (m, 2H, CH2), 1.2 (m, 16H, CH2), 0.9 (t, 3H, CH3, J ¼
6.7 Hz) ppm.
13C-NMR (DMSO-d6): d ¼ 170.8 (C]O), 51.6 (1C, CH), 31.3,
28.9, 28.9, 28.7, 28.68, 28.66, 28.4, 26.8, 22.1 (9C, CH2), 13.9 (1C,
CH3) ppm.
5-(1H,1H,2H,2H,3H,3H,4H,4H,5H,5H,6H,6H)-Peruorodecyl-
barbituric acid 3b-[6,4]. Yield: 49%, (0.36 g), C14H15F9N2O3
(430.09). MS m/z: 430 (M+).
IR n ¼ 3217, 3102, 2916, 2847, 1697, 1427, 1357, 1211, 1126,
1041, 918 cmꢁ1
.
1H-NMR (DMSO-d6): d ¼ 12.8 (s, 2H, NH), 3.2 (t, 1H, CH, J ¼
7.4 Hz), 2.3–2.1 (m, 2H, CH2), 1.7 (m, 2H, CH2), 1.5 (m, 2H,
CH2), 1.3 (m, 6H, CH2) ppm.
9 (a) D. Goldmann, D. Janietz, C. Schmidt and J. H. Wendorff,
J. Mater. Chem., 2004, 14, 1521; (b) A. Kohlmeier and
D. Janietz, Liq. Cryst., 2007, 34, 289.
13C-NMR (DMSO-d6): d ¼ 171.8 (C]O), 52.3 (1C, CH), 33.9,
29.2, 28.8, 27.4, 22.4, 20.4 (6C, CH2) ppm.
´
10 (a) J. Barbera, L. Puig, P. Romero, J. L. Serrano and T. Sierra,
19F-NMR (CDCl3): d ¼ ꢁ81.5 (3F, CF3), ꢁ115.1 (2F, CH2CF2),
ꢁ125.0 (2F, CF3CF2CF2), ꢁ126.5 (2F, CF3CF2) ppm.
5-Decyl-1-methyl-barbituric acid 3c. Yield: 79% (1.38 g),
Chem. Mater., 2005, 17, 3763; (b) J. Barbera, L. Puig,
´
P. Romeo, J. L. Serrano and T. Sierra, J. Am. Chem. Soc.,
´
2005, 127, 458; (c) J. Barbera, L. Puig, P. Romero,
C
15H26N2O3 (282.19). MS m/z: 282 (M+).
J. L. Serrano and T. Sierra, J. Am. Chem. Soc., 2006, 128,
4487; (d) S. Coco, C. Cordovilla, C. Dominguez, B. Donnio,
P. Espinet and D. Guillon, Chem. Mater., 2009, 21, 3282.
IR n ¼ 3300–3000, 2916, 2847, 1705, 1566, 1519, 1465, 1303,
1265, 918 cmꢁ1
.
1H-NMR (DMSO-d6): d ¼ 3.35 (t, 1H, CH, J ¼ 6.5 Hz), 3.0 (s, 11 (a) A. Kohlmeier and D. Janietz, Chem. Mater., 2006, 18, 59;
3H, CH3), 2.1 (m, 2H, CH2), 1.2 (m, 16H, CH2), 0.85 (t, 3H, CH3, J
¼ 6.8 Hz) ppm.
(b) D. Janietz and A. Kohlmeier, Mol. Cryst. Liq. Cryst.,
2009, 509, 39; (c) A. Kohlmeier, A. Nordsieck and
D. Janietz, Chem. Mater., 2009, 21, 491; (d) T. Vlad-
Bubulak, J. Buchs, A. Kohlmeier, M. Bruma and D. Janietz,
Chem. Mater., 2007, 19, 4460; (e) A. Kohlmeier and
D. Janietz, Chem.–Eur. J., 2010, 16, 10453.
1-Methyl-5-(1H,1H,2H,2H,3H,3H,4H,4H,5H,5H,6H,6H)-per-
uorodecyl-barbituric acid 3d-[6,4]. Yield: 55% (0.42 g),
C
15H17F9N2O3 (444.11). MS m/z: 444 (M+).
IR n ¼ 3300–3000, 2940, 2862, 1705, 1473, 1419, 1357, 1203,
1126, 1042, 918 cmꢁ1
.
12 (a) B. E. Smart, in Organouorine Chemistry Principles and
Commercial Applications, ed. R. E. Benks and J. C. Tatlow,
Plenum Press, New York, 1994; (b) M. P. Kra and
1H-NMR (CDCl3): d ¼ 9.1 (br, 1H, NH), 3.7 (t, 1H, CH, J ¼ 6.4
Hz), 2.8 (s, 3H, CH3), 2.1 (m, 2H, CH2), 2.0 (m, 2H, CH2), 1.6 (m,
2H, CH2), 1.4 (m, 6H, CH2), 0.9 (t, 3H, CH3, J ¼ 7.7 Hz) ppm.
19F-NMR (CDCl3): d ¼ ꢁ81.5 (3F, CF3), ꢁ115.1 (2F, CH2CF2),
ꢁ125.0 (2F, CF3CF2CF2), ꢁ126.5 (2F, CF3CF2) ppm.
´
J. G. Riess, Chem. Rev., 2009, 109, 1714; (c) S. Hernandez-
Ainsa, M. Marcos, J. Barbera and J. L. Serrano, Angew.
Chem., Int. Ed., 2010, 49, 1990; (d) B. M. Rosen,
C. J. Wilson, D. A. Wilson, M. Peterca, M. R. Imam and
V. Percec, Chem. Rev., 2009, 109, 6275; (e) C. Tschierske,
Top. Curr. Chem., 2012, 318, 1; (f) G. Ungar, C. Tschierske,
V. Abetz, R. Holyst, M. A. Bates, F. Liu, M. Prehm,
R. Kieffer, X. Zeng, M. Walker, B. Glettner and
A. Zywocinski, Adv. Funct. Mater., 2011, 21, 1296.
Acknowledgements
This work was supported by the BMBF-Initiative “Spitzenfor-
¨
schung und Innovation in den neuen Landern” within the
¨
cooperative project “Taschentuchlabor – Impulszentrum fur
13 (a) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto,
D. N. Chin, M. Mammen and D. M. Gordon, Acc. Chem. Res.,
1995, 28, 37; (b) D. S. Lawrence, T. Jiang and M. Levitt, Chem.
Rev., 1995, 95, 2229; (c) L. J. Prins, D. N. Reinhoudt and
P. Timmermann, Angew. Chem., 2001, 113, 2447; (d)
P. Timmermann and L. J. Prins, Eur. J. Org. Chem., 2001,
3191.
Integrierte Bioanalyse” (FKZ 03IS2201C).
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Soft Matter