Bent-shaped mesogenic oxadiazoles and thiadiazoles with terminal methyl group

Phase Transitions

Volumn 83, Issue 8, 2010, Pages 634-649

  Prajapati, A K ^a   Modi, Vishal ^a  

^a M S UNIVERSITY OF BARODA   (India)

Author keywords

bent shaped; mesomorphism; oxadiazoles; thiadiazoles

Indexed keywords

ALKOXYPHENYL; BENZOYL CHLORIDES; ELEMENTAL ANALYSIS; HETEROCYCLIC MOIETIES; LAWESSON'S REAGENTS; MESOGENICS; MESOMORPHIC PROPERTY; MESOPHASES; METHYL BENZOIC ACID; METHYL GROUP; NEMATIC MESOPHASES; OXADIAZOLES; RELATED COMPOUNDS; ROD-SHAPED; SPECTROSCOPIC METHOD; THIADIAZOLES;

CHLORINE COMPOUNDS; HYDROCARBONS;

SPECTROSCOPIC ANALYSIS;

EID: 77955444529     PISSN: 01411594     EISSN: 10290338     Source Type: Journal    
DOI: 10.1080/01411594.2010.505341     Document Type: Article

References (60)

1. D. Demus and H. Zaschke, Flussige Kristalle in Tabellen, VEB Deutscher Verlag fur Grudnstoffindustrie, Leipzig, 1984.
2. (a) K. Dimitrowa, J. Hauschild, H. Zaschke, and H. Schubert, Kristallin-flüssige 1,3,4-Thiadiazole. I. Biphenyl-und terphenylanaloge 1,3,4-Thiadiazole, J. Prakt. Chem. 322 (1980), pp. 933-944
3. (b) W. Schafer, U. Rosenfelf, H. Zaschke, H. Stettin, and H. Kresse, Kristallinflüssige 1,3,4-Thiadiazole. II [1]. 1,3,4-Thiadiazole mit Cyclohexanstrukturfragmenten, J. Prakt. Chem. 331 (1989), pp. 631-636
4. (c) C. Tschierske, H. Zaschke, H. Kresse, A. Madicke, D. Denus, D. Girdziunaite, and G.Y. Bak, Liquid crystalline thiadiazole derivatives IV new liquid crystalline materials with broad smectic C ranges, Mol. Cryst. Liq. Cryst. 191 (1990), pp. 223-230
5. (d) C. Tschierske, D. Joachimi, H. Zaschke, H. Kresse, B. Linstrom, G. Pelzl, D. Demus, and G.Y. Bak, Liquid crystalline thiadiazole derivatives V: new ferroelectric thiaoiazole derivatives, Mol. Cryst. Liq. Cryst. 191 (1990), pp. 231-235.
6. V. Vill, Liquid Crystal 2.0: Database of Liquid Crystalline Compounds for Personal Computers: Fijitsu Kyushu System (FQS) Ltd, Fukuoka, LCI, Hamburg, 1996.
7. (a) B. Bahadur, Liquid crystal displays, Mol. Cryst. Liq. Cryst. 109 (1984), pp. 3-93
8. (b) V.Y. Zyryanov, E.P. Pozhidaev, S.L. Smorgon, A.L. Andreev, D. Ganzke, V.F. Shabanov, I.N. Kompanets, and W. Haase, Light modulation characteristics of a single-polarizer electrooptical cell based on polymer dispersed ferroelectric liquid crystals, Liq. Cryst. 28 (2001), pp. 741-748.
9. T. Niori, T. Sekine, J. Watanbe, T. Furukawa, and H. Takezoe, Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules, J. Mater. Chem. 6 (1996), pp. 1231-1233.
10. (a) G. Pelzl, S. Diele, and W. Weissflog, Banana-shaped compounds: a new field of liquid crystals, Adv. Mater. 11 (1999), pp. 707-724
11. (b) M.B. Ros, J.L. Serrano, M.R. Fuente, and C.L. Folcil, Banana-shaped liquid crystals: a new field to explore, J. Mater. Chem. 15 (2005), pp. 5093-5098.
12. (a) G. Pelzl, M.G. Tamba, S. Findeisen-Tandel, M.W. Schröder, U. Baumeister, S. Diele, and W. Weissflog, New bent-core mesogens with carbon-carbon multiple linkages in the terminal chains, J. Mater. Chem. 18 (2008), pp. 3017-3031
13. (b) F.C. Yu and L.J. Yu, Mesophases of achiral bent molecules, Chem. Mater. 18 (2006), pp. 5410-5420
14. (c) C.L. Folcia, J. Ortega, J. Etxebarria, I. Pintre, and M.B. Ros, Achiral bent core liquid crystals with azo and azoxy linkages: structural and non-linear optical properties and photoisomerization, Chem. Mater. 18 (2006), pp. 4617-4626.
15. (a) C. Chai, Q. Yang, X. Fan, X. Chen, Z. Shen, and Q. Zhou, Synthesis, characterisation and liquid crystal properties of 2,5-bis[5-alkyl(alkoxy)phenyl- 1,3,4-oxadiazole]bromobenzenes, Liq. Cryst. 35 (2008), pp. 133-141
16. (b) J. Han, J.-Y. Wang, F.-Y. Zhang, L.-R. Zhu, M.-L. Pang, and J.-B. Meng, Synthesis and mesomorphic behaviour of heterocycle-based liquid crystals containing 1,3,4-oxadiazole/thiadiazole and thiophene units, Liq. Cryst. 35 (2008), pp. 1205-1214
17. (c) M.L. Para, P.I. Hidalgo, E.A. Soto-Bustamante, E.Y. Barbera, and V.-H. Trujillo-Rojo, Novel chiral calamitic liquid crystalline oxadiazoles as ferroelectric materials, Liq. Cryst. 35 (2008), pp. 1251-1262
18. (d) S. Qu and M. Li, Tetrahedron, 63 (2007), pp. 12429-12436
19. (e) C.-R. Wen, Y.-J. Wang, H.-C. Wang, H.-S. Sheu, G.-H. Lee, and C.-K. Lai, Columnar metallomesogen derived from 1,3,4-oxadizole and X-ray crystal structure of dichlorobis[2,5-bis(3,4,5-trimethoxyphenyl)1,3,4-oxadizole] palladium (II), Chem. Mater. 17 (2005), pp. 1646-1654.
20. (a) J. Han, F.-Y. Zhang, Z. Chen, J.-Y. Wang, L.-R. Zhu, M.-L. Pang, and J.-B. Meng, Synthesis and liquid crystalline properties of substituted 2,5-diaryl 1,3,4-oxadiazole derivatives without flexible chains, Liq. Cryst. 35 (2008), pp. 1359-1365
21. (b) C. Wang, L.-O. Palsson, A.S. Batsanov, and M.R. Bryce, Molecular wire comprising-extended ethynyl-and butadiynyl-2,5-diphenyl-1,3,4-oxadizole derivatives: synthesis, redox, structural and optoelectronic properties, J. Am. Chem. Soc. 128 (2006), pp. 3789-3799
22. (c) J. Han, S.S.-X. Chui, and C.M. Che, Thermotropic liquid crystals based on extended 2,5-disubstituted-1,3,4-oxadiazoles: structureproperty relationships, variable-temperature powder X-ray diffraction, and small-angle X-ray scattering studies, Chem. Asian. J. 1 (2006), pp. 814-825
23. (d) G. Hughes, D. Kreher, C. Wang, A.S. Batsanov, and M. Bryce, Ethynyl-extended 2,5-diphenyl-1,3,4-oxadiazoles and 2-phenyl 5-(2-thienyl)-1,3,4-oxadiazoles: synthesis, X-ray crystal structures and optical properties, Org. Biomol. Chem. 2 (2004), pp. 3363-3367.
24. W. Weissflog, H. Ná dasi, U. Dunemann, G. Pelzl, S. Diele, A. Eremin, and H. Kresse, Influence of lateral substituents on the mesophase behaviour of banana-shaped mesogens, J. Mater. Chem. 11 (2001), pp. 2748-2758.
25. R. Cristiano, F. Ely, and H. Gallardo, Light-emitting bent-shape liquid crystals, Liq. Cryst. 32 (2005), pp. 15-25.
26. S. Kang, Y. Saito, N. Watanabe, M. Tokita, Y. Takanishi, H. Takezoe, and J. Watanabe, Low-birefringent, chiral banana phase below calamatic Nematic and/or smectic C phases in oxadiazole derivatives, J. Phys. Chem. B 110 (2006), pp. 5205-5214.
27. (a) A. Hetzheim, C. Wesner, J. Werner, H. Kresse, and C. Tschierske, Liquid crystalline and dielectric properties of homologous series of substituted 1,3,4-oxadiazoles, Liq. Cryst. 26 (1999), pp. 885-891
28. (b) D. Girdziunaite, C. Tschierske, E. Novotna, H. Kresse, and A. Hetzheim, New mesogenic 1,3,4-oxadiazole derivatives, Liq. Cryst. 10 (1991), pp. 397-407
29. (c) K.J.K. Semmler, T.J. Dingemans, and E.T. Samulski, Non-linear boomerang-shaped liquid crystals derived from 2,5-bis(p-hydroxyphenyl)-1,3,4- oxadiazole, Liq. Cryst. 27 (2000), pp. 131-136.
30. (c) R. Cristiano, A.A. Vieira, F. Ely, and H. Gallardo, Synthesis and characterization of luminescent hockey stick-shaped liquid crystalline compounds, Liq. Cryst. 33 (2006), pp. 381-390.
31. H.H. Sung and H.C. Lin, Effect of polar substituents on the properties of 1,3,4-oxadiazole-based liquid crystalline materials containing asymmetric cores, Liq. Cryst. 31 (2004), pp. 831-841.
32. (a) S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hägele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, and M. Tosoni, Discotic liquid crystals: from tailormade synthesis to plastic electronics, Angew. Chem. Int. Ed. 46 (2007), pp. 4832-4887
33. (b) J.W.Y. Lam and B.Z. Tang, Liquid-crystalline and light-emitting polyacetylenes, J. Polym. Sci. Part A: Polym. Chem. 41 (2003), pp. 2607-2629
34. (c) M.P. Aldred, A.J. Eastwood, S.P. Kitnery, G.J. Richards, P. Vlachos, S.M. Kelly, and M. O'Neill, Synthesis and mesomorphic behaviour of novel light-emitting liquid crystals, Liq. Cryst. 32 (2005), pp. 1251-1262
35. (d) M.P. Aldred, A.J. Eastwood, S.M. Kelly, P. Vlachos, A.E.A. Contorst, S.R. Farrar, B. Mansoor, M. O'Neill, and W.C. Tsoi, Light emitting fluorine photoreactive liquid crystal for organic electroluminescence, Chem. Mater. 16 (2004), pp. 4928-4936.
36. (a) P. Zhang, S.N. Qu, H.T. Wang, B.L. Bai, and M. Li, A new series of liquid-crystalline bi-1,3,4-oxadiazole derivatives: synthesis and mesomorphic behaviour, Liq. Cryst. 35 (2008), pp. 389-394
37. (b) C.-K. Lai, Y.-C. Ke, J.-C. Su, C.-S. Lu, and W.-R. Li, Heterocyclic 1,3,4-oxadiazole as columnar core, Liq. Cryst. 29 (2002), pp. 915-920
38. (c) B.G. Kim, S. Kim, and S.Y. Park, Star-shaped discotic nematic liquid crystal containing 1,3,5-triethynylbenzene and oxadiazole-based rigid arms, Tetrahedron Lett. 42 (2001), pp. 2697-2699.
39. (a) A. Seed, Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core, Chem. Soc. Rev. 36 (2007), pp. 2046-2069
40. (b) M.L. Parra, C.G. Saavedra, P.I. Hidalgo, and E.Y. Elgueta, Novel chiral liquid crystals based on amides and azo compounds derived from 2-amino-1,3,4-thiadiazoles: synthesis and mesomorphic properties, Liq. Cryst. 35 (2008), pp. 55-64
41. (c) M. Sato, M. Notsu, and S. Nakashima, The relationship between the structures of semi-rigid homo-and copolyesters based on 5,50-diphenyl-2,20- bis(1,3,4-thiadiazole)s and their liquid crystalline and optical properties, Liq. Cryst. 31 (2004), pp. 1195-1205.
42. C.-T. Liao, Y.-J. Wang, C.-S. Huang, H.-S. Sheu, G.-H. Lee, and C.K. Lai, New metallomesogens derived from unsymmetric 1,3,4-thiodiazoles: synthesis, single crystal structure, mesomorphism, and optical properties, Tetrahedron 63 (2007), pp. 12437-12445.
43. (a) I. Thomsen, U. Pedersen, P.B. Rasmussen, B. Yde, T.P. Andersen, and S.-O. Lawesson, Novel and convenient methods for the preparation of substituted thiophenes, thiazoles, and 1,3,4-thiadiazole-2(3h)-thiones from bifunctional substrates, Chem. Lett. (1983), 809-810
44. (b) B. Sybo, P. Bradley, A. Grubb, S. Miller, K.J.W. Proctor, L. Clowes, M.R. Laawrie, P. Sampson, and A.J. Seed, 1,3,4-Thiadiazole-2-carboxylate esters: new synthetic methodology for the preparation of an elusive family of self-organizing materials, J. Mater. Chem. 17 (2007), pp. 3406-3411
45. (c) M. Sato and R. Ohta, Liquid crystalline semirigid polyesters based on phenylstilbene analogues of 1,3,4-thiadiazole, Liq. Cryst. 34 (2007), pp. 295-303.
46. R.M. Srivastava, R.A.W. Neves Filho, R. Schneider, A.A. Vieira, and H. Gallardo, Synthesis, optical properties and thermal behaviour of 1,3,4-oxadiazole-based twin dimers, Liq. Cryst. 35 (2008), pp. 737-742.
47. A.K. Prajapati and V.P. Modi, Bent shaped mesogenic oxadiazole and thiadiazole derivatives from rod shaped mesogenic hydrazide containing polar chloro group, Liq. Cryst. 47 (2010), pp. 407-415.
48. G.A. Olah, S.C. Narang, and A. Garcia-Luna, Synthetic methods and reactions; 971. Sulfuryl chloride fluoride-mediated esterification of carboxylic acids with alcohols, Synthesis (1981), pp. 790-791.
49. J.S. Dave, and R.A.Vora, Liquid Crystals and Ordered Fluids, J.F Johonson and R.S. Porter, eds., Plenum Press, New York, 1970.
50. (a) G.W. Gray, In Steric Effects in Conjugated Systems, G.W. Gray, ed., Butterworths, London, 1958
51. (b) G.W. Gray, Molecular Structure and Properties of Liquid Crystals, Academic Press, London, 1962.
52. (a) G.W. Gray and B. Jones, Mesomorphism and chemical constitution. Part I. The n-alkoxy naphthoic acids, J. Chem. Soc. (1954), pp. 683-686
53. (b) G.W. Gray and B. Jones, Mesomorphism and chemical constitution. Part II. The trans-p-n-alkoxy cinnamic acids, J. Chem. Soc. (1954), pp. 1467-1470
54. (c) G.W. Gray and B. Jones, Mesomorphism and chemical constitution. Part III. The effect of halogen substitution on the mesomorphism of the 4-alkoxybenzoic acids, J. Chem. Soc. (1954), pp. 2556-2562
55. (d) G.W. Gray and B. Jones, Mesomorphism and chemical constitution. Part IV. The effect of substitution on the mesomorphism of the 6-n-alkoxy-2-naphthoic acids, J. Chem. Soc. (1955), pp. 236-244
56. (e) G.W. Gray, J.B. Hartley and B. Jones, Mesomorphism and chemical constitution. Part V. The mesomorphic properties of the 40-nalkoxydiphenyl-4- carboxylic acids and their simple alkyl esters, J. Chem. Soc. (1955), pp. 1412-1420
57. (f) G.W. Gray, J.B. Hartley, A. Ibbotson and B. Jones, Mesomorphism and chemical constitution. Part VI. Certain mono-and di-anils of the benzene, diphenyl, fluorene, and fluorenone series, J. Chem. Soc. (1955), pp. 4359-4368
58. (g) G.W. Gray, B. Jones and F. Marson, Mesomorphism and chemical constitution. Part VII. The effect of halogen substitution on the mesomorphism of the trans-p-n-alkoxycinnamic acids, J. Chem. Soc. (1956), pp. 1417-1423
59. (h); G.W. Gray, B. Jones and F. Marson, Mesomorphism and chemical constitution. Part VIII. The effect of 30-substituents on the mesomorphism of the 40-n-alkoxydiphenyl-4-carboxylic acids and their alkyl esters, J. Chem. Soc. (1957), pp. 393-401
60. (i) G.W. Gray and A. Ibbotson, Mesomorphism and chemical constitution. Part IX. The preparation and mesomorphic behaviour of the 7-n-alkoxy-fluorene- and-fluorenone-2-carboxylic acids and their n-propyl esters, J. Chem. Soc. (1957), pp. 3228-3235.