Mesomorphic studies of novel azomesogens having a benzothiazole core: Synthesis and characterisation

References

• Marin , L , Damaceanu , MD and Timpu , DS. 2009 . New thermotropic liquid crystalline polyazomethines containing luminescent mesogens . Soft Materials , 7 : 1 – 20 .
   Web of Science ®Google Scholar
• Bhowmik , PK , Han , H , Nedeltchev , AK. , Mandal , HD , Jimenez Hernandez , JA , McGannon , PM , Lopez , L , Kang , SW and Kumar , S. 2009 . Synthesis and characterization of thermotropic liquid-crystalline properties of azomethine dimers . Liq Cryst , 36 : 1389 – 1399 .
   Web of Science ®Google Scholar
• Luckhurst , GR and Gray , GW , eds. 1979 . The molecular physics of liquid crystals , London : Academic Press .
   Google Scholar
• Gelbart , WM. 1982 . Molecular theory of nematic liquid crystals . J Phys Chem , 86 : 4298 – 4307 .
   Web of Science ®Google Scholar
• Matharu , AS and Chambers , AD. 2007 . Structure–property investigation of 2‐ and 3‐thienylacrylates bearing laterally fluorinated azobenzene moieties . Liq Cryst , 34 : 1317 – 1336 .
   Web of Science ®Google Scholar
• Gallardo , H , Magnago , RF and Bortoluzzi , AJ. 2001 . Synthesis, characterization and mesomorphic properties of Ag(i) and Pd(ii) complexes containing the pyridyl and tetrazoyl rings: Crystal structure of [C30H46N10AgClO4] . Liq Cryst , 28 : 1343 – 1352 .
   Web of Science ®Google Scholar
• Mills , JT , Gleeson , HF , Goodby , J , Hird , M , Seed , AJ and Styring , P. 1998 . X-ray and optical studies of the tilted phases of materials exhibiting antiferroelectric, ferrielectric and ferroelectric mesophases . J Mater Chem , 8 : 2385 – 2390 .
   Web of Science ®Google Scholar
• Chan , Y , Xianyu , H , Sun , J , Kula , P , Dabrowski , R , Triopathi , S , Twieg , RJ and Wu , ST. 2011 . Low absorption liquid crystals for mid-wave infrared applications . Optics Express , 19 : 10843 – 10848 .
   PubMed Web of Science ®Google Scholar
• Scolari , L , Wei , L , Gauza , S , Wu , ST and Bjarklev , A. 2011 . Low loss liquid crystal photonic band gap fiber in the near-infrared region . Opt Rev , 18 : 114 – 116 .
   Web of Science ®Google Scholar
• Wu , ST. 1998 . Absorption measurements of liquid crystals in the ultraviolet, visible, and infrared . J Appl Phys , 84 : 4462 – 4465 .
   Web of Science ®Google Scholar
• Efron , U , Wu , ST , Grinberg , J and Hess , LD. 1985 . Liquid crystal-based visible-to-infrared dynamic image converter . Opt Eng , 24 : 111 – 118 .
   Web of Science ®Google Scholar
• Schadt , M. 1997 . Liquid crystal materials and liquid crystal displays . Ann Rev Mater Sci , 27 : 305 – 379 .
   Web of Science ®Google Scholar
• Sung , SJ , Cho , KY and Park , JK. 2004 . Photo-induced liquid crystal alignment of poly(vinyl cinnamate) and fluorinated polyimide blends . Mater Sci Eng C , 24 : 181 – 184 .
   Web of Science ®Google Scholar
• Bartmann , E. 1993 . Flüssigkristalle mit fluorhaltigen alkylgruppen [Liquid crystals with fluorine-containing alkyl groups] . Ber Bunsen Phys Chem , 97 : 1349 – 1351 .
   Web of Science ®Google Scholar
• Ozaki , M. 1987 . Dielectric properties of new stable ferroelectric liquid crystals with large spontaneous polarization . J Chem Phys , 86 : 3648 – 3654 .
   Web of Science ®Google Scholar
• Wu , ST , Hsu , CS and Chen , YN. 1992 . Fluorinated diphenyldiacetylene and tolane liquid crystals with low threshold voltage . Appl Phys Lett , 61 : 2275 – 2277 .
   Web of Science ®Google Scholar
• Sugimori , S , Nigorikawa , K and Goto , Y . inventor . Japan patent JP 6,168,467 . 1986 .
   Google Scholar
• Zhang , SS , Ren , R , Li , XM , Li , Q , Song , XY and Wei , QL. 2006 . Bulk heterojunction photovoltaic cells based on room temperature liquid crystalline tetrathiafulvalene derivatives . Liq Cryst , 33 : 795 – 801 .
   Web of Science ®Google Scholar
• Wu , ST and Lin , CY. 2006 . The effect of lateral fluoro substituents on the mesomorphic properties of semi‐fluorinated chiral liquid crystals . Liq Cryst , 33 : 953 – 960 .
   Web of Science ®Google Scholar
• Hird , M. 2007 . Fluorinated liquid crystals: Properties and applications . Chem Soc Rev , 36 : 2070 – 2095 .
   PubMed Web of Science ®Google Scholar
• Hird , M and Toyne , KJ. 1998 . Fluoro substitution in thermotropic liquid crystals . Mol Cryst Liq Cryst , 323 : 1 – 67 .
   Web of Science ®Google Scholar
• Matsui , M , Kamino , Y , Hayashi , M , Funabiki , K , Shibata , K , Muramatsu , H , Abe , Y and Kaneko , M. 1998 . Fluorine-containing benzothiazolyl bisazo dyes: Their application to guest–host liquid crystal displays . Liq Cryst , 25 : 235 – 240 .
   Web of Science ®Google Scholar
• Konstantinova , LS , Rakitin , OA , Rees , CW , Souvorova , LI , Torroba , T , White , AJP and Williams , DJ. 1999 . One-pot synthesis of new liquid crystalline indeno heterocyclic material . Chem Commun , : 73 – 74 .
   Web of Science ®Google Scholar
• Mallia , A , George , M and Das , S. 1999 . Photochemical phase transition in hydrogen-bonded liquid crystals . Chem Mater , 11 : 207 – 208 .
   Web of Science ®Google Scholar
• Bialecka , FE , Orzeszko , A , Sledzinska , I and Gorecka , E. 1999 . Evidence of the smectic antiphase C* in 4-decyloxybiphenyl ester imide derivatives . J Mater Chem , 9 : 371 – 374 .
   Web of Science ®Google Scholar
• Lin , HC , Ko , CW , Guo , K and Cheng , TW. 1999 . Supramolecular liquid crystals containing isoquinoline hydrogen-bonded acceptors . Liq Cryst , 26 : 613 – 618 .
   Web of Science ®Google Scholar
• Boden , N , Borner , RC , Bushby , RJ and Clements , J. 1994 . First observation of an n-doped quasi-one-dimensional electronically-conducting discotic liquid crystal . J Am Chem Soc , 116 : 10807 – 10808 .
   Web of Science ®Google Scholar
• Seed , AJ. 2007 . Synthesis of self-organizing mesogenic materials containing a sulfur- based five-membered heterocyclic core . Chem Soc Rev , 36 : 2046 – 2069 .
   PubMed Web of Science ®Google Scholar
• Parra , M , Belmar , J , Zunza , H , Zuniga , C , Villouta , S and Martinez , R. 1993 . Synthesis of amides derived from 1,3,4-thiadiazole as mesogenic unit . Bol Soc Chil Quim , 38 : 325 – 330 .
   Google Scholar
• Petrov , VF , Pavluchenko , AI and Smirnova , NI. 1995 . New liquid crystalline pyridine derivatives . Mol Cryst Liq Cryst , 265 : 47 – 53 .
   Web of Science ®Google Scholar
• Campbell , NL , Duffy , WL , Thomas , GI , Wild , JH , Kelly , SM , Bartle , K , O'Neill , M , Minter , V and Tuffin , RP. 2002 . Nematic 2,5-disubstituted thiophenes . J Mater Chem , 12 : 2706 – 2721 .
   Web of Science ®Google Scholar
• Vlachos , P , Mansoor , B , Aldred , MP , O'Neill , M and Kelly , SM. 2005 . Charge-transport in crystalline organic semiconductors with liquid crystalline order . Chem Commun , : 2921 – 2923 .
   PubMed Web of Science ®Google Scholar
• Sekine , C , Konya , N , Minai , M and Fujisawa , K. 2001 . Synthesis and properties of high birefringence liquid crystals: Thiophenylacetylene and benzothiazolylacetylene derivatives . Liq Cryst , 28 : 1361 – 1367 .
   Web of Science ®Google Scholar
• Prajapati , AK and Bonde , NL. 2009 . Mesogenic benzothiazole derivatives with a polar nitro substituent . Mol Cryst Liq Cryst , 501 : 72 – 85 .
   Web of Science ®Google Scholar
• Aldred , MP , Vlachos , P , Dong , D , Kitney , SP , Tsoi , WC , O'Neill , M and Kelly , SM. 2005 . Heterocyclic reactive mesogens: Synthesis, characterisation and mesomorphic behavior . Liq Cryst , 32 : 951 – 965 .
   Web of Science ®Google Scholar
• Yeap , GY , Alshargabi , A , Masato , MI , Mahmood , WAK and Takeuchi , D. 2012 . Synthesis and anisotropic properties of azo-bridged benzothiazole-phenyl esters . Mol Cryst Liq Cryst , 557 : 126 – 133 .
   Web of Science ®Google Scholar
• Dutta , GK , Guha , S and Patil , S. 2010 . Synthesis of liquid crystalline benzothiazole-based derivatives: A study of their optical and electrical properties . Org Electron , 11 : 1 – 9 .
   Web of Science ®Google Scholar
• Ha , ST , Koh , TM , Lin , HC , Yeap , GY , Win , YF , Ong , ST , Shivasothy , S. and Ong , LK. 2009 . Heterocyclic benzothiazole-based liquid crystals: Synthesis and mesomorphic properties . Liq Cryst , 36 : 917 – 925 .
   Web of Science ®Google Scholar
• Ha , ST , Koh , TM , Lin , HC , Boeq , PL , Win , YF , Ong , ST and Ong , LK. 2009 . Synthesis and mesomorphic properties of 2-(4-alkyloxyphenyl)benzothiazoles . Mol Cryst Liq Cryst , 506 : 56 – 70 .
   Web of Science ®Google Scholar
• Ha , ST , Koh , TM , Lee , SL , Yeap , GY , Lip , CH and Ong , ST. 2010 . Synthesis of new Schiff base ester liquid crystals with a benzothiazole core . Liq Cryst , 37 : 547 – 554 .
   Web of Science ®Google Scholar
• Ha , ST , Koh , TM , Yeap , GY , Lin , HC , Beh , JK , Win , YF and Boey , PL. 2009 . New mesogenic Schiff base esters comprising a benzothiazole moiety: Synthesis and mesomorphic properties . Chin Chem Lett , 20 : 1081 – 1084 .
   Web of Science ®Google Scholar
• Prajapati , AK and Bonde , NL. 2006 . Mesogenic benzothiazole derivatives with methoxy substituents . J Chem Sci (Bangalore, India) , 118 : 203 – 210 .
   Web of Science ®Google Scholar
• Chavan , AA and Pai , NR. 2007 . Synthesis and biological activity of N-substituted-3- chloro-2-azetidinones . Molecules , 12 : 2467 – 2477 .
   PubMed Web of Science ®Google Scholar
• Tokunaga , K , Takayashiki , Y , Iino , H and Hanna , J. 2009 . Electronic conduction in nematic phase of small molecules . Phys Rev B , 79 : 1 – 4 .
   Google Scholar
• Tokunaga , K , Iino , H and Hanna , J. 2009 . Charge carrier transport properties in liquid crystalline 2-phenylbenzothiazole derivatives . Mol Cryst Liq Cryst , 510 : 241 – 249 .
   Web of Science ®Google Scholar
• Tokunaga , K , Takayashiki , Y , Iino , H and Hanna , J. 2009 . One-dimensional to three- dimensional electronic conduction in liquid crystalline mesophases . Mol Cryst Liq Cryst , 510 : 250 – 258 .
   Web of Science ®Google Scholar
• Dutta , GK , Guha , S and Patil , S. 2010 . Synthesis of liquid crystalline benzothiazole-based derivatives: A study of their optical and electrical properties . Org Electron , 11 : 1 – 9 .
   Web of Science ®Google Scholar
• Funahashi , M and Hanna , J. 1996 . Photoconductive behavior in Smectic A phase of 2-(4ʹ-heptyloxyphenyl)-6-dodecylthiobenzothiazole . Jpn J Appl Phys , 35 : L703
   Web of Science ®Google Scholar
• Funahashi , M and Hanna , J. 1997 . Fast hole transport in a new calamitic liquid crystal of 2-(4′-heptyloxyphenyl)-6-dodecylthiobenzothiazole . Phys Rev Lett , 78 : 2184 – 2187 .
   Web of Science ®Google Scholar
• Seed , AJ , Pantalone , K , Sharma , U and Grubb , AM. 2009 . A new synthesis of alkylsulphanylnaphthalenes and the synthesis and mesomorphic properties of novel naphthylisothiocyanates . Liq Cryst , 36 : 329 – 338 .
   Web of Science ®Google Scholar
• Sadashiva , BK and Gropalakrishnan , CR. 1998 . Ferroelectric liquid crystalline polysiloxanes containing a naphthalene moiety . Macromol Rapid Commun , 19 : 97 – 102 .
   Web of Science ®Google Scholar
• Sierra , T , Serrano , JL , Rose , MB , Ezcurra , A and Zubia , J. 1992 . Synthesis and study of new α-haloacid ferroelectric liquid crystal derivatives. MM2 approach to the molecular structure–ferroelectric activity relationship . J Am Chem Soc , 114 : 7645 – 7651 .
   Web of Science ®Google Scholar
• Wedler , W , Demus , D , Zaschke , H , Mohr , K , Schafer , KW and Weissflog , W. 1991 . Vitrification in low molecular weight mesogenic compounds . J Mater Chem , 1 : 347 – 356 .
   Web of Science ®Google Scholar
• Wu , SL and Hsieh , W. 1999 . Thresholdless antiferroelectricity in a novel chiral swallow-tailed liquid crystal . J Mater Chem , 11 : 852 – 854 .
   Web of Science ®Google Scholar
• Mochizuki , A , Motoyoshi , K and Nakatsuka , MA. 1991 . High contrast and high transmittance multiplexing SSFLC display utilizing naphthalene-based liquid crystal materials . Ferroelectrics , 122 : 37 – 51 .
   Web of Science ®Google Scholar
• Suste , A , Moslavac , D and Sunjic , V. 1996 . Synthesis and mesomorphic properties of naphth-2-yl 2-pyridylmethyl ketones and their copper (ii) complexes . Liq Cryst , 21 : 383 – 388 .
   Web of Science ®Google Scholar
• Marcos , M , Omenat , A , Serrano , JL , Sierra , T and Ezcurra , A. 1992 . A ferroelectric liquid crystal dimer: Synthesis and properties . Adv Mater , 4 : 285 – 287 .
   Web of Science ®Google Scholar
• Hird , M , Toyne , KJ and Gray , GW. 1993 . Palladium-catalysed cross-coupling reactions in the synthesis of some high polarizability materials . Liq Cryst , 14 : 741 – 761 .
   Web of Science ®Google Scholar
• Gray , GW and Jones , B. 1954 . The preparation of 4- and 5-n-alkoxy-1-naphthoic and 6- and 7-n-alkoxy-2-naphthoic acids . J Chem Soc , : 678 – 683 .
   Web of Science ®Google Scholar
• Gray , GW and Jones , B. 1954 . Mesomorphism and chemical constitution, Part III: The effect of halogen substitution on the mesomorphism of the 4-alkoxy benzoic acids . J Chem Soc , : 2556 – 2562 .
   Web of Science ®Google Scholar
• Gray , GW and Jones , B. 1955 . Mesomorphism and chemical constitution, Part IV: The effect of substitution on the mesomorphism of the 6-n-alkoxy-2-naphthoic acids . J Chem Soc , : 236 – 244 .
   Web of Science ®Google Scholar
• Dave , JS and Prajapati , AP. 1975 . Pramana Suppl , 1 : 435
   Google Scholar
• Dave , JS and Prajapati , AP. 1976 . Mesomorphic behaviour of some Schiff base compounds comprising a naphthalene moiety . Curr Sci India , 45 : 95
   Web of Science ®Google Scholar
• Jones , B. 1935 . Apparent cases of liquid crystal formation in p-alkoxy benzoic acids . J Chem Soc , : 1874
   Google Scholar
• Johnson , JF and Porter , RS , eds. 1970 . Liquid crystals and ordered fluids , New York : Plenum Press .
   Google Scholar
• Kaufmann , HP. 1928 . Die Bildung von Thiazol-Derivaten bei der Rhodanierung von Aminen [The formation of thiazole derivatives by thiocyanation of amines] . Archiv Pharm , 266 : 197 – 218 .
   Google Scholar
• Hird , M , Seed , AJ , Toyne , KJ , Goodby , JW , Gray , GW and McDonnell , DG. 1993 . Synthesis, transition temperatures and optical anisotropy of some isothiocyanato-substituted biphenyls . J Mater Chem , 3 : 851 – 859 .
   Web of Science ®Google Scholar
• Hatakeyama , T , Kondo , Y , Fujiwara , Y , Takaya , H , Ito , S , Nakamura , E and Nakamura , M. 2009 . Iron-catalysed fluoroaromatic coupling reactions under catalytic modulation with 1,2-bis(diphenylphosphino)benzene . Chem. Commun , : 1216 – 1218 .
   PubMed Web of Science ®Google Scholar
• Gray , GW. 1962 . Molecular structure and properties of liquid crystals , London : Academic Press .
   Google Scholar
• Sackmann , H and Demus , D. 1966 . The polymorphism of liquid crystals . Mol Cryst Liq Cryst , 2 : 81 – 102 .
   Web of Science ®Google Scholar
• Gray , GW and Goodby , JW. 1984 . Smectic liquid crystals: textures and structures , Glasgow and London : Leonard Hill .
   Google Scholar
• Prajapati , AK and Bonde , NL. Mesogenic Schiff's base ester with chloroethyl tail . Proceedings of the 11th National Conference on Liquid Crystals . Allahabad , India.
   Google Scholar
• Vora , RA and Prajapati , AK. Mesomorphic properties of azo mesogens containing a terminal naphthalene nucleus . Proceedings of the 5th National Seminar of Liquid Crystals, Thapar Institute of Engineering and Technology . Patiala , India.
   Google Scholar
• Jadav , ND , Prajapati , BA and Prajapati , AK. 2003 . Azomesogens containing two fused ring moieties: Synthesis and characterization . Mol Cryst Liq Cryst , 399 : 53 – 60 .
   Web of Science ®Google Scholar
• Pavluchenko , AI , Smirnova , NI , Titov , VV , Kovahev , EI and Djumaev , KM. 1976 . Nematic liquid crystals containing pyridine and benzazole rings . Mol Cryst Liq Cryst , 37 : 35 – 46 .
   Web of Science ®Google Scholar