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Original Articles

Novel 5-(4-alkoxyphenyl)thieno[3,2-b]thiophene-2-carboxylate esters: Highly efficient synthesis and mesogenic evaluation of a new class of materials exhibiting the smectic C phase

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Pages 515-530 | Received 02 Jan 2012, Accepted 11 Jan 2012, Published online: 13 Feb 2012

References

  • Northrup , J.E. 2011 . Appl. Phys. Lett , 99 : 062111 – 062113 .
  • Nakayama , K. , Hirose , Y. , Soeda , J. , Yoshizumi , M. , Uemura , T. , Uno , M. , Li , W. , Kang , M.J. , Yamagishi , M. , Okada , Y. , Miyazaki , E. , Nakazawa , Y. , Nakao , A. , Takimiya , K. and Takeya , J. 2011 . Adv. Mater , 23 : 1626 – 1629 .
  • Niimi , K. , Shinamura , S. , Osaka , I. , Miyazaki , E. and Takimiya , K. 2011 . J. Am. Chem. Soc , 133 : 8732 – 8739 .
  • Sánchez-Carrera , R.S. , Atahan , S. , Schrier , J. and Aspuru-Guzik , A. 2010 . J. Phys. Chem. C , 114 : 2334 – 2340 .
  • Sokolov , A.N. , Atahan-Evrenk , S. , Mondal , R. , Akkerman , H.B. , Sánchez-Carrera , R.S. , Granados-Focil , S. , Schrier , J. , Mannsfeld , S.C.B. , Zoombelt , A.P. , Bao , Z. and Aspuru-Guzik , A. 2011 . Nat. Commun , 2 : 437 article number
  • Seo , J.H. , Namdas , E.B. , Gutacker , A. , Heeger , A.J. and Bazan , G.C. 2010 . Appl. Phys. Lett , 97 043303/043301043303/043303
  • de la Fuente Vornbrock , A. , Sung , D. , Kang , H. , Kitsomboonloha , R. and Subramanian , V. 2010 . Org. Electron , 11 : 2037 – 2044 .
  • Kong , H. , Lee , D.H. , Seo , J.-I. , Oh , J.-Y. , Chung , D.S. , Park , J.-W. , Kwon , S.-K. , Lee , Y.S. , Park , C.E. and Shim , H.-K. 2010 . ACS Appl. Mater. Interfaces , 2 : 1100 – 1106 .
  • Madathil , P.K. , Heinrich , B. , Donnio , B. , Mathevet , F. , Fave , J.-L. , Guillon , D. , Attias , A.-J. , Lee , C. , Kim , T.-D. and Lee , K.-S. 2010 . J. Nanosci. Nanotechnol , 10 : 6800 – 6804 .
  • Deng , D. , Yang , Y. , Zhang , J. , He , C. , Zhang , M. , Zhang , Z.-G. , Zhang , Z. and Li , Y. 2011 . Org. Electron , 12 : 614 – 622 .
  • Akbaşoğlu , N. , Balan , A. , Baran , D. , Cirpan , A. and Toppare , L. 2010 . J. Polym. Sci., Part A: Polym. Chem , 48 : 5603 – 5610 .
  • Biniek , L. , Chochos , C. L. , Hadziioannou , G. , Leclerc , N. , Lévêque , P. and Heiser , T. 2010 . Macromol. Rapid Commun , 31 : 651 – 656 .
  • Yang , C. , Li , B. , Tong , J. and Xia , Y. 2011 . Polym. Sci., Ser. A , 53 : 469 – 479 .
  • Zhang , G. , Fu , Y. , Xie , Z. and Zhang , Q. 2011 . Macromolecules , 44 : 1414 – 1420 .
  • Fu , Y. , Shen , W. and Li , M. 2011 . Polym. Int , 60 : 211 – 221 .
  • Metri , N. , Sallenave , X. , Beouch , L. , Plesse , C. , Goubard , F. and Chevrot , C. 2010 . Tetrahedron Lett , 51 : 6673 – 6676 .
  • García , G. , Granadino-Roldán , J.M. , Garzón , A. , Moral , M. , Peña-Ruiz , T. , Navarro , A. , Fernández-Liencres , M.P. and Fernández-Gómez , M. 2010 . J. Phys. Chem. C , 114 : 12325 – 12334 .
  • Yue , R. , Chen , S. , Lu , B. , Liu , C. and Xu , J. 2011 . J. Solid State Electrochem , 15 : 539 – 548 .
  • Burkhardt , S.E. , Conte , S. , Rodriguez-Calero , G.G. , Lowe , M.A. , Qian , H. , Zhou , W. , Gao , J. , Hennig , R.G. and Abruña , H.D. 2011 . J. Mater. Chem , 21 : 9553 – 9563 .
  • McEntee , G.J. , Skabara , P.J. , Vilela , F. , Tierney , S. , Samuel , I.D.W. , Gambino , S. , Coles , S.J. , Hursthouse , M.B. , Harrington , R.W. and Clegg , W. 2010 . Chem. Mater , 22 : 3000 – 3008 .
  • Gipson , R.M. , Sampson , P. and Seed , A.J. 2010 . Liq. Cryst , 37 : 101 – 108 .
  • Litvinov , V.P. and Gol'dfarb , Y.a L. 1976 . Adv. Heterocycl. Chem , 19 : 123 – 214 .
  • Comel , A. , Sommen , G. and Kirsch , G. 2004 . Mini-Rev. Org. Chem , 1 : 367 – 374 .
  • Litvinov , V.P. 2006 . Adv. Heterocycl. Chem , 90 : 125 – 203 .
  • Fuller , L.S. , Iddon , B. and Smith , K.A. 1997 . J. Chem. Soc., Perkin Trans. 1 , : 3465 – 3470 .
  • Trofimov , B.A. , Sobenina , L.N. , Mikhaleva , A.I. , Sergeeva , M.P. , Nesterenko , R.N. , Golovanova , N.I. and Polovnikova , P.I. 1992 . Chem. Heterocycl. Compd , 28 : 403 – 405 .
  • Baker , B.R. , Querry , M.V. , Safir , S.R. and Bernstein , S. 1947 . J. Org. Chem , 12 : 138 – 154 .
  • Guseinov , K.Z. , Gambarov , D.G. , Mirzoeva , M.A. , Mamedov , F.N. and Fati–Zade , R.F. 1977 . Azerb. Khim. Zh , : 105 – 107 .
  • Seliger , H. and Görtz , H.-H. 1980 . Synth. Commun , 10 : 175 – 182 .
  • Hanif , R.M. , Qineng , P. and Fenzhu , M. 1998 . Chem. Pharm. Bull , 46 : 1428 – 1431 .
  • Lüttringhaus , A. and Prinzbach , H. 1959 . Justus Liebigs Ann. Chem , 624 : 79 – 97 .
  • Malik , A.K. and Atamjyot; Rao , A.L.J. 1993 . Indian J. Chem., Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem , 32 : 1015 – 1016 .
  • Snyder , H.R. , Stewart , J.M. , Allen , R.E. and Dearborn , R.J. 1946 . J. Am. Chem. Soc , 68 : 1422 – 1428 .
  • Wong , H.-L. , Tao , C.-H. , Zhu , N. and Yam , V.W.-W. 2011 . Inorg. Chem , 50 : 471 – 481 .
  • Sánchez-Carrera , R.S. , Odom , S.A. , Kinnibrugh , T.L. , Sajoto , T. , Kim , E.-G. , Timofeeva , T.V. , Barlow , S. , Coropceanu , V. , Marder , S.R. and Brédas , J.-L. 2010 . J. Phys. Chem. B , 114 : 749 – 755 .
  • Sato , M. , Kitamura , T. , Masiko , T. and Unoura , K. 2008 . J. Organomet. Chem , 693 : 247 – 256 .
  • Yamamoto , T. , Toyota , K. and Morita , N. 2010 . Tetrahedron Lett , 51 : 1364 – 1366 .
  • Choi , H. , Raabe , I. , Kim , D. , Teocoli , F. , Kim , C. , Song , K. , Yum , J.-H. , Ko , J. , Nazeeruddin , M.K. and Gratzel , M. 2010 . Chem.-Eur. J , 16 : 1193 – 1201 .
  • Zhang , G. , Bala , H. , Cheng , Y. , Shi , D. , Lv , X. , Yu , Q. and Wang , P. 2009 . Chem. Commun , : 2198 – 2200 .
  • Ahmed , M.O. , Wang , C. , Keg , P. , Pisula , W. , Lam , Y.-M. , Ong , B. S. , Ng , S.-C. , Chen , Z.-K. and Mhaisalkar , S.G. 2009 . J. Mater. Chem , 19 : 3449 – 3456 .
  • Kong , H. , Lee , D.H. , Kang , I.-N. , Lim , E. , Jung , Y.K. , Park , J.-H. , Ahn , T. , Yi , M.H. , Park , C.E. and Shim , H.-K. 2008 . J. Mater. Chem , 18 : 1895 – 1902 .
  • Takimiya , K. , Niihara , N. and Otsubo , T. 2005 . Synthesis , : 1589 – 1592 .
  • Lim , E. , Jung , B.-J. and Shim , H.-K. 2003 . Macromolecules , 36 : 4288 – 4293 .
  • Tsivgoulis , G.M. and Lehn , J.-M. 1995 . Angew. Chem. Int. Ed , 34 : 1119 – 1122 .
  • Peters , D. , Hörnfeldt , A.-B. and Gronowitz , S. 1990 . J. Heterocycl. Chem , 27 : 2165 – 2173 .
  • Molander , G.A. and Ellis , N. 2007 . Acc. Chem. Res , 40 : 275 – 286 .
  • Molander , G.A. and Canturk , B. 2009 . Angew. Chem. Int. Ed , 48 : 9240 – 9261 .
  • Darses , S. and Genet , J.-P. 2008 . Chem. Rev , 108 : 288 – 325 .
  • Knapp , D.M. , Gillis , E.P. and Burke , M.D. 2009 . J. Am. Chem. Soc , 131 : 6961 – 6963 .
  • Gillis , E.P. and Burke , M.D. 2007 . J. Am. Chem. Soc , 129 : 6716 – 6717 .
  • Gray , G.W. and Goodby , J.W. 1976 . Mol. Cryst. Liq. Cryst , 37 : 157 – 188 .
  • Goodby , J.W. and Gray , G.W. 1976 . J. Phys. (Paris) , 37 : 17 – 26 .
  • Nassif , L. , Jakli , A. and Seed , A.J. 2001 . Mol. Cryst. Liq. Cryst , 365 : 171 – 179 .

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