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Bent Shaped 1,3,4-Oxadiazole/Thiadiazole heterocyclic rings containing liquid crystals

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Abstract

Two series of bent shaped 1,3,4-oxadiazole/thiadiazole heterocyclic ring containing liquid crystalline (LC) compounds were synthesized and characterized by FT-IR, 1H, 13C-NMR and ESI-Mass spectroscopic techniques. Liquid crystal properties were investigated by polarized optical microscopy and differential scanning calorimetry. All the compounds exhibited mesophases such as nematic, smectic A and smectic C phases. The liquid crystalline effects were ascertained by changing the central atom in the heterocyclic ring and by increasing the length of the terminal alkyloxy chains which bring considerable improvements on the mesomorphic properties. The absorption and emission spectral studies of all the compounds were investigated and confirmed.

Two series of bent shaped azomethine-containing low molecular weight organic liquid crystalline compounds containing 1,3,4-oxadiazole/thiadiazole derivatives are reported. These compounds are also fluorescent.

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References

  1. (a) Pantalone K and Seed A J 2002 Liq. Cryst. 29 945; (b) Gayathri K, Balamurugan S and Kannan P 2011 J. Chem. Sci. 123 255; (c) Palani T, Saravanan C and Kannan P 2011 J. Chem. Sci. 123 81

  2. (a) Kulkarni A P, Tonzola C J, Babel A and Jeneke S A 2004 Chem. Mater. 16 4556; (b) Cristiano R, Vieira A A, Ely F and Gallardo H 2006 Liq. Cryst. 33 381; (c) Cristiano R, Santos DMPO and Gallardo H 2005 Liq. Cryst. 32 7

  3. Torgova S I, Geivandova T A, Francescangeli O and Strigazzi A 2003 Pramana. J. Phys. 61 239

    Article  CAS  Google Scholar 

  4. Cioanca E R, Carlescu I, Wilson D and Scutaru D 2010 Rev. Chem. 61 1158

    CAS  Google Scholar 

  5. (a) Kang S, Saito Y, Watanabe N, Tokita M, Takanishi Y, Takezoe H and Watanabe J 2006 J. Phys. Chem. B. 110 5205; (b) Hughes G, Kreher D, Wang C, Batsanov A S and Bryce M R 2004 Org. Biomole. Chem. 22 3363

  6. (a) Kamtekar K T, Wang C, Bettington S, Batsanov A S, Perepichka I F, Bryce M R, Ahan J H, Rabinal M and Petty M C 2006 J. Mater. Chem. 16 3823; (b) Han J, Chui S S Y and Che C M 2006 Chem. Asian. J. 1 814

  7. Alderete J, Belmar J, Parra M, Zuniga C and Jimenez V 2003 Liq. Cryst. 30 1319

    Article  CAS  Google Scholar 

  8. Gray G W and Goodby J W 1976 Mol. Cryst. Liq. Cryst. 37 157

    Article  CAS  Google Scholar 

  9. Ahn J H, Wang C, Pearson C, Bryce M R and Petty M C 2004 Appl. Phys. Lett. 85 1283

    Article  CAS  Google Scholar 

  10. Parra M, Belmar J, Zunza H, Zuniga C, Villouta S H and Martinez R 1995 J. Prakt. Chem. 337 325

    Article  CAS  Google Scholar 

  11. Dimitrowa K, Hauschild J, Zaschke H and Schubert H 1980 J. Prakt. Chem. 322 933

    Article  Google Scholar 

  12. Mochizuki H, Hasui Y, Kawamoto M, Shiono T, Ikeda T, Adachi C, Taniguchi Y and Shirota Y 2000 Chem. Comm. 19 1923

    Article  Google Scholar 

  13. Han J, Wang J Y, Zhang F Y, Zhu L R, Pang M L and Meng J B 2008 Liq. Cryst. 35 1205

    Article  CAS  Google Scholar 

  14. Han J, Zhang F Y, Chen Z, Wang J Y, Zhu L R, Pang M L and Meng J B 2008 Liq. Cryst. 35 1359

    Article  CAS  Google Scholar 

  15. Han J, Chang X Y, Zhu L R, Wang Y M, Meng J B and Chui S S Y 2008 Liq. Cryst. 5 1379

    Article  Google Scholar 

  16. Zhang P, Qu S N, Wang H T, Bai B L and Li M 2008 Liq. Cryst. 35 389

    Article  CAS  Google Scholar 

  17. Chai C P, Yang Q, Fan X H, Chen X F, Shen Z H and Zhou Q F 2008 Liq. Cryst. 35 133

    Article  CAS  Google Scholar 

  18. Srivastava R M, Neves Filho R A W, Schneider R, Vieira A A and Gallardo H 2008 Liq. Cryst. 35 737

    Article  CAS  Google Scholar 

  19. Wen C R, Wang Y J, Wang H C, Sheu H S, Lee G H and Lai C K 2005 Chem. Mater. 17 1646

    Article  CAS  Google Scholar 

  20. Kim B G, Kim S and Park S Y 2001 Tetrahedron Lett. 42 2697

    Article  CAS  Google Scholar 

  21. Yeap G Y, Ooi Y H, Uchida N and Mito M M 2014 J. Chem. Sci. 126 847

    Article  CAS  Google Scholar 

  22. Sato M, Notsu M and Nakashima S 2004 Liq. Cryst. 31 1195

    Article  CAS  Google Scholar 

  23. Liao C T, Wang Y J, Huang C S, Sheu H S, Lee G H and Lai C K 2007 Tetrahedron 63 12437

    Article  CAS  Google Scholar 

  24. Thomsen I, Pedersen U, Rasmussen P B, Yde B, Andersen T P and Lawesson S O 1983 Chem. Lett. 6 809

    Article  Google Scholar 

  25. Sybo B, Bradley P, Grubb A, Miller S, Proctor K J W, Clowes L, Laawrie M R, Sampson P and Seed A J 2007 J. Mater. Chem. 17 3406

    Article  CAS  Google Scholar 

  26. Perin D D and Aramarego W L F 1998 In Purification of laboratory chemicals (New York: Pergamon Press)

  27. Hamciuc E, Hamciuc C, Bruma M and Schulz B 2005 Euro. Poly. J. 41 2989

    Article  CAS  Google Scholar 

  28. Marin L, Damaceanu M D and Timpu D 2009 Soft. Mater. 7 1

    Article  CAS  Google Scholar 

  29. Tasaganva R G, Kariduraganvar M Y and Inamdar S R 2009 Synth. Met. 159 1812

    Article  CAS  Google Scholar 

  30. Prajapati A K and Bonde N L 2006 J. Chem. Sci. 118 203

    Article  CAS  Google Scholar 

  31. Vijaysrinivasan M, Kannan P and Roy A 2012 Liq. Cryst. 39 1465

    Article  CAS  Google Scholar 

  32. Wang H, Zhang F, Bai B, Zhang P, Shi J, Yu D, Zhao Y, Wang Y and Li M 2008 Liq. Cryst. 35 905

    Article  CAS  Google Scholar 

  33. Srivastava R M, Neves Filho R A W, Schneider R, Vieira A A and Gallardo H 2008 Liq. Cryst. 35 737

    Article  CAS  Google Scholar 

  34. Pathak S K, Gupta R K, Nath S, Shankar Rao D S, Prasad S K and Achalkumar A S 2015 J. Mater. Chem. C 3 2940

    Article  CAS  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the University Grants Commission, New Delhi, Government of India for the financial support [39-691/2010 (SR)]. Instrumentation facility provided under FIST-DST and DRS-UGC to Department of Chemistry, Anna University are sincerely acknowledged.

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Correspondence to PALANINATHAN KANNAN.

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Supplementary Information

Spectral and DSC data are given (figures S1–S5 and S6) which are available at www.ias.ac.in/chemsci.

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SELVARASU, C., KANNAN, P. Bent Shaped 1,3,4-Oxadiazole/Thiadiazole heterocyclic rings containing liquid crystals. J Chem Sci 127, 1831–1838 (2015). https://doi.org/10.1007/s12039-015-0949-0

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