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Original Articles

Synthesis and thermotropic studies of a novel series of nematogenic liquid crystals 2-(6-alkoxynaphthalen-2-yl)-5-cyanopyridines

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Pages 922-931 | Received 14 Nov 2012, Accepted 13 Mar 2013, Published online: 14 Apr 2013

References

  • Paraskos , PA and Swager , TM. 2002 . Effects of desymmetrization on thiophene-based bent-rod mesogens . Chem Mater , 14 : 4543 – 4549 .
  • Singh , S. 2002 . Liquid crystals: fundamentals . London: World Scientific , : 92 – 173 . Chapter 4, Nematic liquid crystals
  • Collings , PJ and Hird , M. 1997 . Introduction to liquid crystals: chemistry and physics . London: Taylor and Francis , : 43 – 77 . Chapter 3, Calamitic liquid crystals - nematic and smectic mesophases
  • Nash , JA and Gray , GW. 1974 . Studies of some heterocyclic mesogens . Mol Cryst Liq Cryst , 25 : 299 – 321 .
  • Burrow , MP , Gray , GW and Lacey , KJ. 1988 . The synthesis and liquid crystal properties of some 2,5-disubstituted pyridines . Liq Cryst , 3 : 1643 – 1653 .
  • Gray , GW. 1976 . “ Molecular geometry and the properties of nonamphiphilic liquid crystals ” . In Advances in liquid crystals , Edited by: Brown , GH . Vol. 2 , New York : Academic Press .
  • Hird , M , Gray , GW and Toyne , KJ. 1991 . Cross-coupling reactions in the synthesis of liquid crystals . Mol Cryst Liq Cryst , 206 : 187 – 204 .
  • Karamysheva , LA , Kovshev , EI , Pavluchenko , AI , Roitman , KV , Titov , VV , Torgova , SI and Grebenkin , MF. 1981 . New heterocyclic liquid crystalline compounds . Mol Cryst Liq Cryst , 67 : 241 – 252 .
  • Grebenkin , MF , Petrov , VF , Belyaev , VV , Pavluchenko , AI , Smirnova , NI , Lovshev , EI , Titov , VV and Ivashchenko , AV. 1985 . Synthesis and properties of 5-alkyl-2-(4-cyanophenyl)pyridines . Mol Cryst Liq Cryst , 129 : 245 – 257 .
  • Pavlyuchenko , AI , Smirnova , NI , Mikhailova , TA , Kovshev , EI and Titov , VV. 1986 . Synthesis of 2-(4-alkylphenyl)- and 2-(4-alkoxyphenyl)-5-cyanopyridines and their liquid-crystal characteristics . Zh Org Khim , 22 : 1061 – 1065 .
  • Kelly , SM , Funfschilling , J and Villiger , A. 1993 . Smectic C phenylpyridines with an alkenyloxy chain . Liq Cryst , 14 : 1169 – 1180 .
  • Kelly , SM and Funfschilling , J. 1996 . Novel 2-(4-octylphenyl) pyridine-5-yl alkanoates and alkenoates: influence of dipoles and chain conformation on smectic C formation . Liq Cryst , 20 : 77 – 93 .
  • Getmanenko , YA , Twieg , RJ and Ellman , BD. 2006 . 2,5-dibromopyridine as a key building block in the synthesis 2,5-disubstituted pyridine-based liquid crystals . Liq Cryst , 33 : 267 – 288 .
  • Asano , T , Uenoyama , M , Moriya , K , Yano , S , Takatani , S and Kagabu , S. 1997 . Polymorphism in a homologous series of 2-(4-alkoxyphenyl)-5-(4-methylphenyl)pyridines . Liq Cryst , 23 : 365 – 369 .
  • Asano , T , Moriya , K , Yano , S , Takatani , S and Kagabu , S. 1998 . Liquid crystalline phase transitions of the 2-(4’-alkoxybiphenyl-4--yl)-5-(4-methylphenyl)pyridines . Liq Cryst , 25 : 263 – 266 .
  • Moriya , K , Harada , F , Yano , S and Kagabu , S. 2000 . The synthesis and liquid crystalline behaviour of 2-(4-n-alkoxyphenyl)-5-methylpyridines . Liq Cryst , 27 : 1647 – 1651 .
  • Molander , GA and Ellis , N. 2007 . Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction . Acc Chem Res , 40 ( 4 ) : 275 – 286 .
  • Molander , GA , Canturk , B and Kennedy , LE. 2009 . Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates . J Org Chem , 74 ( 3 ) : 973 – 980 .
  • Tietz , JI , Mastriana , JR , Sampson , P and Seed , AJ. 2012 . Novel 5-(4-alkoxyphenyl)thienol[3,2-b]thiophene-2-carboxylate esters: highly efficient synthesis and mesogenic evaluation of a new class of materials exhibithing the smectic C phase . Liq Cryst , 39 : 515 – 530 .
  • Chia , WL , Shen , SW and Lin , HC. 2001 . Novel synthesis of liquid crystalline compounds of 5-substituted 2-(4-alkylphenyl)pyridines . Tetrahedron Lett , 42 : 2177 – 2179 .
  • Chia , WL and Cheng , YW. 2008 . Facile synthesis of a series of 2-(4-alkyloxyphenyl)-5-cyanopyridine liquid crystalline compounds . Heterocycles , 75 : 375 – 382 .
  • Chia , WL , Li , CL and Lin , CH. 2010 . Synthesis and mesomorphic studies on the series of 2-(4-alkoxyphenyl)-5-phenylpyridines and 2-(6-alkoxynaphthalen-2-yl)-5-phenylpyridines . Liq Cryst , 37 : 23 – 30 .
  • Chia , WL and Tsai , CY. 2011 . Synthesis and mesomorphic properties of a series of phenyl 6-(4-alkoxyphenyl)nicotinates . Heterocycles , 83 : 1057 – 1065 .
  • Comins , DL and Abdullah , AH. 1982 . Regioselective addition of Grignard reagents to 1-acylpyridinium salts . A convenient method for the synthesis of 4-alkyl(aryl)pyridines. J Org Chem , 47 : 4315 – 4319 .
  • Comins , DL , Stroud , ED and Herrick , JJ. 1984 . Regioselective addition of Grignard reagents to the 1-phenoxycarbonyl salts of alkyl nicotinates . Heterocycles , 22 : 151 – 157 .
  • Imrie , CT and Taylor , L. 1989 . The preparation and properties of low molar mass liquid-crystals possessing lateral alkyl chains . Liq Cryst , 6 : 1 – 10 .
  • Attard , GS and Imrie , CT. 1992 . Liquid-crystalline and glass-forming dimers derived from 1-aminopyrene . Liq Cryst , 11 ( 5 ) : 785 – 789 .
  • Donaldson , T , Staesche , H , Lu , ZB , Henderson , PA , Achard , MF and Imrie , CT. 2010 . Symmetric and non-symmetric chiral liquid crystal dimers . Liq Cryst , 37 ( 8 ) : 1097 – 1110 .
  • Chan , T-N , Lu , ZB , Yam , W-S , Yeap , GY and Imrie , CT. 2012 . Non-symmetric liquid crystal dimers containing an isoflavone moiety . Liq Cryst , 39 ( 3 ) : 393 – 402 .
  • Dierking , I. 2003 . Textures of liquid crystals . Weinheim: Wiley-VCH , : 1 – 20 . Chapter 1, Introduction
  • Gray , GW and Mosley , A. 1976 . Trends in the nematic-isotropic liquid transition temperatures for the homologous series of 4-n-alkoxy and 4-n-alkyl-4’ cyanobiphenyls . J Chem Soc Perkin , II : 97 – 102 .
  • Gonzalez , Y , Ros , MB and Serrano , JL. 1994 . Naphthalene system as the origin of unconventionally shaped ferroelectric liquid crystals . Chem Mater , 6 : 1516 – 1525 .
  • Demus , D , Diele , S , Grande , S and Sackman , H. 1983 . Advances in liquid crystals . New York: Academic Press , 6 : 1 – 107 . Polymorphism in thermotropic liquid crystals
  • Lauk , U , Skrabal , P and Zollinger , H. 1981 . Substituted 2-phenylnaphthalenes, a new class of nematic liquid crystals . Helv Chim Acta , 64 : 1847 – 1848 .
  • Coates , D. 1990 . “ Chemical structure, molecular engineering and mixture formulation ” . In Liquid crystals---applications and uses , Edited by: Bahadur , B . Vol. 1 , 122 – 124 . Singapore : World Scientific .
  • Seed , AJ , Toyne , KJ , Goodby , JW and Hird , M. 2000 . Synthesis, transition temperatures, and optical properties of various 2,6-disubstituted naphthalenes and related 1-benzothiophenes with butylsufanyl and cyano or isothiocyanato terminal groups . J Mater Chem , 10 : 2069 – 2080 .
  • Hird , M , Toyne , KJ , Gray , GW , Day , SE and McDonnell , DG. 1993 . The synthesis and high optical birefringence of nematogens incorporating 2,6-disubstituted naphthalenes and terminal cyano-substituents . Liq Cryst , 15 : 123 – 150 .

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