PDF herunterladen
Synthesis 2008(4): 605-609  
DOI: 10.1055/s-2008-1032156
PAPER
© Georg Thieme Verlag Stuttgart · New York

Sonogashira Coupling Applied in the Synthesis of 1,2,4-Oxadiazole-Based Nonsymmetrical Liquid Crystals

Hugo Gallardo*a, Rodrigo Cristianoa, André A. Vieiraa, Ricardo A.W. Neves Filhob, Rajendra M. Srivastava*b
a Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil
Fax: +55(48)37216850 ; e-Mail: hugo@qmc.ufsc.br ;
b Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE 50740-540, Brazil
Weitere Informationen

Publikationsverlauf

Received 9 October 2007
Publikationsdatum:
31. Januar 2008 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A series of highly π-conjugated nonsymmetrical liquid crystals, based on the core 3,5-(disubstituted)-1,2,4-oxadiazole with a shape similar to a hockey stick, were successfully synthesized by convergent Sonogashira coupling reaction between the building blocks of aryl iodides and the corresponding terminal arylacetylenes, using 3-[4-(decyloxy)phenyl]-5-(haloaryl)-1,2,4-oxadiazoles or decyl 4-iodobenzoate (10) and terminal arylacetylenes. This versatile synthetic route yielded luminescent mesogens with smectic and nematic phases, typical of calamitic compounds.

Key words

Sonogashira coupling - liquid crystals - 1,2,4-oxadi­azoles - acetylenes

    References

  • 1a Spieker B. Hahn A. Vill V. Synthesis  2002,  2129 
    Crossref
  • 1b Feuerbacher N. Vögtle F. Windscheidt J. Poetsch E. Nieger M. Synthesis  1999,  117 
    Crossref
  • 1c Pickaert G. Ziessel R. Synthesis  2004,  2716 
    Crossref
  • 1d Lee ASY. Wu CC. Lin LS. Hsu HF. Synthesis  2004,  568 
    Crossref
  • 1e Lee SK. Naito Y. Shi L. Tokita M. Takezoe H. Watanabe J. Liq. Cryst.  2007,  935 
    Crossref
  • 1f Prajapati AK. Patel HN. Liq. Cryst.  2007,  903 
    Crossref
  • 2a Vlachos P. Mansoor B. Aldred MP. O’Neill M. Kelly SM. Chem. Commun.  2005,  2921 
    Crossref
  • 2b O’Neill M. Kelly SM. Adv. Mater. (Weinheim, Ger.)  2003,  1135 
    Crossref
  • 3a Cristiano R. Santos DMPO. Gallardo H. Liq. Cryst.  2005,  7 
    Crossref
  • 3b Cristiano R. Ely F. Gallardo H. Liq. Cryst.  2005,  15 
    Crossref
  • 3c Cristiano R. Vieira AA. Ely F. Gallardo H. Liq. Cryst.  2006,  381 
    Crossref
  • 3d Gallardo H. Magnago R. Bortoluzzi AJ. Liq. Cryst.  2001,  1343 
    Crossref
  • 4 Wu S.-T. Finkenzeller U. Rieffenrath JJ. Appl. Phys.  1989,  4372 
  • 5a Sonogashira K. J. Organomet. Chem.  2002,  46 
  • 5b Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Suche in Google Scholar
  • 6a Vieira AA. Cristiano R. Bortoluzzi AJ. Gallardo H. J. Mol. Struct.  2007,  in press ; DOI: 10.1016/j.molstruc.2007.05.006
    Crossref
  • 6b Vasconcelos UB. Dalmolin E. Merlo AA. Org. Lett.  2005,  7:  1027 
    CrossrefSuche in Google Scholar
  • 6c Tong LH. Pascu SI. Jarrosson T. Sanders JKM. Chem. Commun.  2006,  1085 
    Crossref
  • 7 Dingemans TJ. Murthy NS. Samulski ET. J. Phys. Chem. B  2001,  8845 
    Crossref
  • 8 Lee JW. Kang SU. Lim JO. Choi HK. Jin MK. Toth A. Pearce LV. Tran R. Wang Y. Szabo T. Blumberg PM. Bioorg. Med. Chem.  2004,  12:  371 
    CrossrefSuche in Google Scholar
  • 9 Tiemann F. Ber. Dtsch. Chem. Ges.  1884,  17:  126 
    CrossrefSuche in Google Scholar
  • 10 Melissaris AP. Litt MH. J. Org. Chem.  1992,  57:  6998 
    CrossrefSuche in Google Scholar
  • 11 Mal’kina AG. Brandsma L. Vasilevsky SF. Trofimov BA. Synthesis  1986,  589 
  • 12a Merlo AA. Braun JE. Vasconcelos UB. Ely F. Gallardo H. Liq. Cryst.  2000,  657 
    Crossref
  • 12b Ely F. Conte G. Merlo AA. Gallardo H. Liq. Cryst.  2004,  1413 
    Crossref
  • 13 Grassmann S. Sadek B. Ligneau X. Elz S. Ganellin CR. Arrang JM. Schwartz JC. Stark H. Schunack W. Eur. J. Pharm. Sci.  2002,  15:  367 
    CrossrefSuche in Google Scholar
  • 14 Break P. Musick TJ. Chen CW. J. Am. Chem. Soc.  1988,  110:  3538 
    CrossrefSuche in Google Scholar