H, d, ThH, J~4 Hz), 7.60 (2 H, d, ArH, J~8 Hz), 7.82 (1 H, d,
ThH, J~4Hz); IR nmax (KBr) 3500±2950 (OH str.), 1702 (CLO
str.), 1253, 1180, 814 cm ; MS, m/z: 360 (M , 2%), 176
ferroelectric phase. This is currently under further investigation
together with elaborate pitch studies on the ®ngerprint texture
of the SmC*antiferroelectric phase. The results of these studies
will be published in a later communication.
2
1
z
(
100%).
(
S)-4'-(1-Methylheptyloxycarbonyl)biphenyl-4-yl 5-(4-n-
decyloxyphenyl)thiophene-2-carboxylate 1
Acknowledgements
1
,3-Dicyclohexylcarbodiimide (0.50 g, 0.0024 mol) and (S)-1-
ASM would like to thank the Royal Society of Chemistry for
the award of a `JWT Jones Travelling Fellowship' in order to
participate in electro-optical characterisation at Chalmers
University of Technology, Sweden, and the Engineering and
Physical Sciences Research Council (research studentship for
C.G.).
methylheptyl 4'-hydroxybiphenyl-4-carboxylate, 6, (0.36 g,
0
2
(
.0014 mol) were added to 5-(4-n-decyloxyphenyl)thiophene-
-carboxylic acid, 5, (0.0014 mol) in dry dichloromethane
25 ml). 4-Dimethylaminopyridine (1±2 crystals) was added as
catalyst and the reaction mixture was left to stir for 2 h at room
temperature. The resultant white precipitate was removed by
®ltration and the ®ltrate was evaporated to dryness under
reduced pressure. The crude residue was puri®ed by ¯ash
chromatography on silica gel eluting with 1 : 1 petroleum ether
References
1
17th International Liquid Crystal Conference, Program and
Abstracts Book, July 19±24, 1998, Centre National de la Recherche
Scienti®que, Universit e Louis-Pasteur de Strasbourg, Strasbourg,
France.
(
bp 60±80 ³C)±dichloromethane followed by repeated crystal-
lisation from ethanol to yield the desired (S)-4'-(1-methylhep-
tyloxycarbonyl)biphenyl-4-yl 5-(4-n-decyloxyphenyl)thio-
phene-2-carboxylate, 1, 0.9 g (64%), as an off-white solid.
The liquid crystalline transition temperatures are listed in
Table 1. Found: C, 75.41, H, 7.82%. C H O S requires C,
2
A. D. L. Chandani, Y. Ouchi, H. Takezoe, A. Fukuda,
K. Terashima, K. Furukawa and A. Kishi, Jpn. J. Appl. Phys.
Part 2, 1989, 28, 1261.
A. Fukuda, Y. Takanishi, T. Isokaki, K. Ishikawa and H. Takezoe,
J. Mater. Chem., 1994, 4, 997.
W. K. Robinson, H. Gleeson, M. Hird, A. J. Seed and P. Styring,
Mol. Cryst. Liq. Cryst., 1997, 299, 19.
D. J. Byron, L. Komitov, A. S. Matharu, I. McSherry and
R. C. Wilson, J. Mater. Chem., 1996, 6(12), 1871.
C. J. Booth, D. A. Dunmur, J. W. Goodby, K. S. Jaskaran and
K. J. Toyne, J. Mater. Chem., 1994, 4(5), 747.
N. Miyaura, T. Yanagi and A. Suzuki, Synth. Commun., 1981, 11,
513.
A. Hassner and V. Alexanian, Tetrahedron Lett., 1978, 4475.
C. Loubser, P. L. Wessels, P. Styring and J. W. Goodby, J. Mater.
Chem., 1994, 4(1), 71.
E. Gorecka, M. Glogarova, H. Sverenyak and L. Lejcek, Ferro-
electrics, 1996, 178, 101.
A. J. Seed, M. Hird, P. Styring, H. Gleeson and J. T. Mills, Mol.
Cryst. Liq. Cryst., 1997, 299, 19.
4
2
52
5
3
4
5
6
7
7
(
5.45, H, 7.78%; d
H
(CDCl
12 H, m, alkyl), 4.0 (2 H, t, ArOCH ), 5.1 (1 H, sextet,
3
3
) 0.9 (6 H, t, 26CH ), 1.28±1.36
2
3
C*(H)CH ), 6.93 (2 H, d, ArH, J~8 Hz), 7.26 (1 H, d, ThH,
J~4 Hz), 7.29 (2 H, d, ArH, J~8Hz), 7.59 (2 H, d,
ArH. J~8Hz), 7.92 (1 H, d, ThH, J~4 Hz), 8.13 (2 H, d,
ArH, J~8 Hz); IR nmax (KBr) 2924, 2854, 1722(CLO),
1
8
709(CLO), 1605, 1449, 1271, 1205, 1165, 1112, 1081, 1019,
21 z
31, 807, 761 cm . MS, m/z: 668 (M , 15%), 539 (15%), 343
2
~11.9 (c, 0.0016 g ml in CHCl
1
(
100%), 203 (96%). [a]
D
3
).
8
9
Conclusion
1
0
1
Complementary optical microscopy, differential scanning
calorimetry, miscibility, and electro-optical and current
response studies show clear evidence for the existence of the
SmA*, SmC*ferroelectric, SmC*ferrielectric, SmC*antiferro-
electric and SmI*antiferroelectric phase types in a novel bent-
shaped chiral compound, namely: (S)-4'-(1-methylheptyloxy-
carbonyl)biphenyl-4-yl 5-(4-n-decyloxyphenyl)thiophene-2-
carboxylate (1). Electro-optical switching is also observed in
a so-called crystal phase which appears below the SmI*anti-
1
12 G. Andersson, PhD Thesis, 1992, Chalmers University, G oÈ teborg,
Sweden.
1
1
1
3
4
5
E. Gorecka, A. D. L. Chandani, Y. Ouchi, H. Takezoe and
A. Fukuda, Jpn. J. Appl. Phys. Part 1, 1990, 29(1), 131.
K. Itoh, M. Kabe, K. Miyachi, Y. Takanishi, H. Takezoe and
A. Fukuda, J. Mater. Chem., 1997, 7(3), 407.
J. W. Goodby, J. S. Patel and F. M. Leslie, Ferroelectrics, 1984, 59,
137.
1310
J. Mater. Chem., 2000, 10, 1303±1310