Skip to main content
SpringerLink
Log in

Synthesis and phase behavior of dendrons derived from 3,4,5-tris(tetradecyloxy)benzoic acid with different functional groups in focal point

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

A number of dendrons of various chain lengths derived from the esters of 3,4,5-tris(tetradecyloxy)benzoic acid were synthesized. These esters were used as building blocks in the design of polyester molecules. Intermediate products, such as branched compounds with variation of functional groups in focal point (aromatic acids and their benzyl esters, aldehydes of different generation) were obtained. The structure and purity of all the compounds were determined by elemental analysis, FT-IR, NMR spectroscopy, mass spectrometry (MALDI-ToF). The phase behavior was investigated by differential scanning calorimetry and confirmed by polarized optical microscopy. Consequently, it was established that the liquid-crystalline properties of this series of dendrons arise from the degree of branching. This behavior can be explained by the formation of hydrogen bonds, as well as microsegregation processes of the links of the macromolecule.

A new series of compounds derived from esters of 3,4,5-tris(tetradecyloxy)benzoic acid were synthesized. It was established that the liquid-crystalline properties of this series of dendrons arise from the degree of branching. This behavior can be explained by the formation of hydrogen bonds as well as processes of microsegregation of the links of the macromolecule.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6

Similar content being viewed by others

References

  1. Newkome G R, Moorefield C N and Voegtle F 2001 In Dendrimers and dendrons: Concepts, syntheses and applications (Weinheim: Wiley-VCH) p. 636

  2. Smith D K, Hirst A R, Love C S, Hardy J G, Brignell S V and Huang B 2005 Prog. Polym. Sci. 30 220

    Article  CAS  Google Scholar 

  3. Bauer S, Fisher H and Ringsdorf H 1993 Angew. Chem.Int. Ed. 32 1589

    Article  Google Scholar 

  4. Pesak D J and Moore J S 1997 Angew. Chem. Int. Ed. 36 1636

    Article  CAS  Google Scholar 

  5. Meier H and Lehmann M 1998 Angew. Chem. Int. Ed. 37 643

    Article  CAS  Google Scholar 

  6. Cameron J H, Facher A, Lattermann G and Diele S 1997 Adv. Mater. 9 398

    Article  CAS  Google Scholar 

  7. Tian Y Q, Kamata K, Yoshita H and Iyoda T 2006 Chem. Eur. J. 12 584

    Article  Google Scholar 

  8. Frauenrath H 2005 Prog. Polym. Sci. 30 325

    Article  CAS  Google Scholar 

  9. Turrin C-O, Maraval V, Leclaire J, Dantras E, Lacabanne C, Caminade A-M and Majoral J-P 2003 Tetrahedron 59 3965

    Article  CAS  Google Scholar 

  10. Ropponen J, Tamminen J, Lahtinen M, Linnanto J, Rissanen K and Kolehmainen E 2005 Eur. J. Org. Chem. 2005 73

    Article  Google Scholar 

  11. Ropponen J, Tuuttila T, Lahtinen M, Nummelin S and Rissanen K 2004 J. Polym. Sci. Part A. 42 5574

    Article  CAS  Google Scholar 

  12. Percec V, Cho W-D, Ungar G and Yeardley D J P 2001 J. Am. Chem. Soc. 123 1302

    Article  CAS  Google Scholar 

  13. Percec V, Won B C, Peterca M and Heiney P A 2007 J. Am. Chem. Soc. 129 11265

    Article  CAS  Google Scholar 

  14. Percec V, Peterca M, Dulcey A E, Imam M R, Hudson S D, Nummelin S, Adelman P and Heiney P A 2008 J. Am. Chem. Soc. 130 13079

    Article  CAS  Google Scholar 

  15. Grebenkin M F and Ivaschenko A V 1989 In Liquid crystalline materials (Moscow: Khimiya) p. 228

  16. Tschierske C 2001 J. Mater. Chem. 11 2647

    Article  CAS  Google Scholar 

  17. Pegenau A, Hegmann T, Tschierske C and Diele S 1999 Chem. Eur. J. 5 1643

    Article  CAS  Google Scholar 

  18. Chervonova U V, Gruzdev M S, Kolker A M, Manin N G and Domracheva N E 2010 Rus. J. Gen. Chem. 80 1954

    Article  CAS  Google Scholar 

  19. Chervonova U V, Gruzdev M S and Kolker A M 2011 Rus. J. Gen. Chem. 81 1853

    Article  CAS  Google Scholar 

  20. Vorobeva V E, Domracheva N E, Pyataev A V, Gruzdev M S and Chervonova U V 2015 Low Tem. Phys. 41 15

    Article  CAS  Google Scholar 

  21. Chervonova U V, Gruzdev M S and Kolker A M 2011 Rus. J. Gen. Chem. 81 2288

    Article  CAS  Google Scholar 

  22. Schaz A, Valaityte E and Lattermann G 2005 Liq. Cryst. 32 513

    Article  CAS  Google Scholar 

  23. Tully D C, Wilder K, Fréchet J M J, Trimble A R and Quate C F 1999 Adv. Mater. 11 314

    Article  CAS  Google Scholar 

  24. Saudan C, Balzani V, Gorka M, Lee S-K, Maestri M, Vicinelli V and Vögtle F 2003 J. Am. Chem. Soc. 125 4424

    Article  CAS  Google Scholar 

  25. Denieul M P, Laursen B, Hazell R and Skrydstrup T 2000 J. Org. Chem. 65 6052

    Article  CAS  Google Scholar 

  26. Shreenivasa Murthy H N and Sadashiva B K 2004 Liq. Cryst. 31 1347

    Article  Google Scholar 

  27. Seeboth Arno, Lotzsch Detlef, Ruhmann Ralf and Muehling Olaf 2014 Chem. Rev. 114 3037

    Article  CAS  Google Scholar 

  28. Ishihara S, Furuki Y and Takeoka S 2008 Polym. Adv. Technol. 19 1097

    Article  CAS  Google Scholar 

  29. Beltrán E., Cavero E., Barberá J, Serrano J L, Elduque A and Giménez R 2009 Chem. Eur. J. 15 9017

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the grant of Russian Foundation for Basic Research No. 14-03-31280-mol_a and the grant of the President of the Russian Federation (No. MK-70.2014.3). Dr. Akopova O.B. is thankful for the grant of Ministry of education and science RF (No. 4.106.2014K). EA, NMR, FT-IR spectroscopy and DSC analysis were carried out by the equipments of Interlaboratory scientific center «Verhnevolzhskij region center of physicochemical researching». The authors would like to thank Dr. Simon Dalgleish (Nagoya University) for useful discussion.

Author information

Authors and Affiliations

  1. G A Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, Ivanovo, 153045, Russia

    MATVEY GRUZDEV, ULYANA CHERVONOVA & ARKADIY KOLKER

  2. Nanomaterials Research Institute, Ivanovo State University, Ivanovo, 153025, Russia

    OLGA AKOPOVA

Authors
  1. MATVEY GRUZDEV
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. ULYANA CHERVONOVA
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. OLGA AKOPOVA
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. ARKADIY KOLKER
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to MATVEY GRUZDEV.

Additional information

Supplementary information (SI)

All additional information pertaining to characterization of the compounds using NMR spectra, FT-IR spectra and mass-spectra are given in the supporting information. The electronic supporting information can be seen in www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOC 2.14 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

GRUZDEV, M., CHERVONOVA, U., AKOPOVA, O. et al. Synthesis and phase behavior of dendrons derived from 3,4,5-tris(tetradecyloxy)benzoic acid with different functional groups in focal point. J Chem Sci 127, 1801–1810 (2015). https://doi.org/10.1007/s12039-015-0945-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-015-0945-4

Keywords

Search

Navigation