Synthesis and Mesomorphic Behavior of New N-Heterotolane Liquid Crystals Containing a Naphthyl-Pyridyl Framework

Ursula B. Vasconcelos; Aloir A. Merlo

doi:10.1055/s-2006-926384

PAPER

Synthesis and Mesomorphic Behavior of New N-Heterotolane Liquid Crystals Containing a Naphthyl-Pyridyl Framework

Ursula B. Vasconcelos, Aloir A. Merlo*
Chemistry Institute, Universidade Federal do Rio Grande do Sul, Av. Bento Gonçalves 9500, Campus do Vale, Porto Alegre, 91501 970 RS, Brazil
Fax: +55(51)33167304; e-Mail: aloir@iq.ufrgs.br;

Abstract

Alle Artikel dieser Rubrik

Abstract

A homologous series of the new N-heterotolane was synthesized using two cross-coupling reactions mediated by copper and palladium/copper. The final compounds present a naphthyl-pyridyl framework connected by an acetylene group. The evaluation of physico-chemical properties is described. All the compounds exhibit the smectic A mesophase.

Key words

liquid crystals - N-heterotolane - naphthyl-pyridyl framework - Buchwald protocol and Sonogashira coupling

Volltext

Referenzen

References

1 Pavluchenko AI. Titov VV. Smirnova NI. Advances in Liquid Crystal Research and Applications Bata L. Pergamon Press; Oxford: 1980.

2 Hird M. Toyne KJ. Gray GW. Liq. Cryst. 1993, 14: 741

3a Siemsen P. Livingston RC. Diederich F. Angew. Chem., Int. Ed. 2000, 39: 2632

3b Schreiber SL. Tan DS. Foley MA. Shair MD. J. Am. Chem. Soc. 1998, 120: 8565

3c Chanteau SH. Tour JM. J. Org. Chem. 2003, 68: 8750

3d Kumar S. Varshney SK. Angew. Chem. Int. Ed. 2000, 39: 3140

3e Collins SK. Glenn PA. Yap GPA. Fallis AG. Org. Lett. 2000, 2: 3189

3f Lützen A. Thiemann F. Meyer S. Synthesis 2002, 2771

3g Lunkwitz R. Tschierske C. Langhoff A. Giebelmann F. Liq. Cryst. 1999, 26: 131

4a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 16: 4467

4b Sonogashira K. Diederich F. Stang PJ. Metal-catalyzed Cross-coupling Reactions Wiley-VCH; Weinheim: 1999.

4c Sonogashira K. Yatake T. TohdaY . Takahashi S. Hagihara N. J. Chem. Soc., Chem. Commun. 1977, 291

4d Negishi E.-I. Anastasia L. Chem. Rev. 2003, 103: 1979

4e Verkade JG. Urgaonkar S. J. Org. Chem. 2004, 69: 5752

5a Hundertmark T. Littke AF. Buchwald SL. Fu GC. Org. Lett. 2000, 2: 1729

5b Takahashi K. Kuroyama Y. Sonogashira K. Hagihara N. Synthesis 1980, 627

6a Vasconcelos UB. Braun JE. Ely F. Gallardo H. Merlo AA. Liq. Cryst. 2000, 27: 657

6b Vasconcelos UB. Dalmolin E. Merlo AA. Org. Lett. 2005, 7: 1027

7a Ullmann F. Ber. Dtsch. Chem. Ges. 1903, 36: 2382

For a review, see:

7b Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

8 Wolter M. Nordmann G. Job GE. Buchwald SL. Org. Lett. 2002, 4: 973

9a Bates CG. Gujadhur RK. Venkataraman D. Org. Lett. 2002, 4: 2803

9b Gujadhur RK. Venkataraman D. Kintigh JT. Tetrahedron Lett. 2001, 42: 4791

9c Shelby Q. Kataoka N. Mann G. Hartwig J. J. Am. Chem. Soc. 2000, 122: 10718

10a Merlo AA. Gallardo H. Synth. Commun. 1993, 23: 2159

10b Merlo AA. Livotto PR. Gallardo H. Taylor TR. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1998, 309: 111

11 Hartley CS. Lemieux RP. Liq. Cryst. 2004, 31: 1101

12 Melissaris AP. Litt MH. Macromolecules 1994, 27: 883

13 Onopchenko A. Sabourin ET. Selwitz CM. J. Org. Chem. 1979, 44: 1233

14 Gray GW. Goodby JW. Smectic Liquid Crystals: Textures and Structures Leonard Hill; Glasgow and London: 1984.

15 Karasz FE. Imrie CT. Attard GS. Macromolecules 1993, 26: 545