Skip to main content
Log in

Synthesis and characterizations of poly(ether)/poly(phenol)s including azomethine coupled benzothiazole side chains: the effect of reaction conditions on the structure, optical, electrochemical, electrical and thermal properties

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

A new Schiff base, 4-((6-ethoxybenzothiazole-2-ylimino)methyl)benzene-1,2-diol (3,4-HBAEBT) was synthesized by the condensation reaction of 3,4-dihydroxybenzaldehyde (3,4-HBA) and 2-amino-6-ethoxybenzothiazole. The Schiff base, then, was converted to its polymer derivatives by oxidative polycondensation reaction in both organic (P-1) and aqueous alkaline medium (P-2). Spectral observations indicated different structural properties for each polymerization condition. Organic and aqueous alkaline medium produced poly(ether) and poly(phenol) structures, respectively. The obtained polymers were separately studied with respect to optical, electrochemical, electrical and thermal properties. With exception of thermal degradation behaviors, the other investigated properties as well as morphological characteristics of both polymers were considerably different. In the fluorescence measurements a solvatochromic effect was recorded and the emission colors of the polymers could be changed as turquoise-green by solvent change.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Scheme 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Kruger H, Janietz S, Sainova D, Wedel A (2003) New organo-soluble conjugated polyquinolines. Macromol Chem Phys 204:1607–1615

    Article  Google Scholar 

  2. Kim K, Sohn BH, Jin JI (2005) Role of Au nanoparticles in efficiency enhancement and green band emission quenching of blue polymer light emitting diodes. J Nanosci Nanotechnol 5:1898–1903

    Article  CAS  Google Scholar 

  3. Duan CH, Wang L, Zhang K, Guan X, Huang F (2011) Conjugated zwitterionic polyelectrolytes and their neutral precursor as electron injection layer for high-performance polymer light-emitting diodes. Adv Mater 23:1665

    Article  CAS  Google Scholar 

  4. Cihaner A, Algı F (2008) An electrochromic and fluorescent polymer based on 1-(1-naphthyl)-2,5-di-2-thienyl-1H-pyrrole. J Electroanal Chem 614:101–106

    Article  CAS  Google Scholar 

  5. Barik S, Bletzacker T, Skene WG (2012) Pi-conjugated fluorescent azomethine copolymers: opto-electronic, halochromic, and doping properties. Maromolecules 45:1165–1173

    Article  CAS  Google Scholar 

  6. Adhikari B, Majumdar S (2004) Polymers in sensor applications. Prog Polym Sci 29:699–766

    Article  CAS  Google Scholar 

  7. Bai H, Shi G (2007) Gas sensors based on conducting polymers. Sensors-Basel 7:267–307

    Article  CAS  Google Scholar 

  8. Ragimov AV, Mamedov BA, Gasanova SG (1997) New efficient dielectric and antistatic materials based on oligoaminophenols. Polym Int 43:343–346

    Article  CAS  Google Scholar 

  9. Kaya İ, Yıldırım M, Kamacı M (2009) Synthesis and characterization of new polyphenols derived from O-dianisidine: the effect of substituent on solubility, thermal stability, and electrical conductivity, optical and electrochemical properties. Eur Polym J 45:1586–1598

    Article  CAS  Google Scholar 

  10. Kaya İ, Bilici A (2007) Synthesis, characterization, thermal analysis, and band gap of oligo-2-methoxy-6-[(4-methylphenyl)imino]methylphenol. J Appl Polym Sci 104:3417–3426

    Article  CAS  Google Scholar 

  11. Yıldırım M, Aydın A, Kaya İ (2012) Syntheses and pH sensing applications of imine-coupled phenol and polyphenol species derived from 2-amino-4-nitrophenol. J Fluoresc 22:961–970

    Article  Google Scholar 

  12. Bilici A, Kaya İ, Şenol D (2011) Phenol side-groups-containing fluorene polymer synthesized by catalytic oxidative polymerization. Polym Advan Technol 22:1953–1958

    Article  CAS  Google Scholar 

  13. Bilici A, Kaya İ, Yıldırım M, Doğan F (2010) Enzymatic polymerization of hydroxy-functionalized carbazole monomer. J Mol Catal B: Enzymatic 64:89–95

    Article  CAS  Google Scholar 

  14. Bilici A, Kaya İ, Yıldırım M (2011) Peroxidase-catalyzed synthesis of polyphenols bearing aldehyde units. Des Monomers Polym 14:353–366

    Article  CAS  Google Scholar 

  15. Kaya İ, Yıldırım M, Aydın A, Şenol D (2010) Synthesis and characterization of fluorescent graft fluorene-co-polyphenol derivatives: the effect of substituent on solubility, thermal stability, conductivity, optical and electrochemical properties. React Funct Polym 70:815–826

    Article  CAS  Google Scholar 

  16. Kaya İ, Yıldırım M, Avcı A (2010) Synthesis and characterization of fluorescent polyphenol species derived from methyl substituted aminopyridine based Schiff bases: the effect of substituent position on optical, electrical, electrochemical, and fluorescence properties. Synth Met 160:911–920

    Article  CAS  Google Scholar 

  17. Cruz J, Garcia-Ochao E, Castro M (2003) Experimental and theoretical study of the 3-amino-1,2,4-triazole and 2-aminothiazole corrosion inhibitors in carbon steel. J Electrochem Soc 150:B26–B35

    Article  CAS  Google Scholar 

  18. Çukurovalı A, Yılmaz İ, Ahmedzade M, Kırbağ S (2001) Antimicrobial activity studies of the metal complexes derived from cyclobutane-substitued thiazole carbamate ligands. Heteroatom Chem 12:665–670

    Article  Google Scholar 

  19. Zhou X, Shao L, Jin Z, Liu J-B, Dai H, Fang J-X (2007) Synthesis and antitumor activity evaluation of some Schiff bases derived from 2-aminothiazole derivatives. Heteroatom Chem 18:55–59

    Article  CAS  Google Scholar 

  20. Maruyama T, Suganuma H, Yamamoto T (1995) Preparation of pi-conjugated polythiazoles and their electrically conducting properties. Synth Met 74:183–185

    Article  CAS  Google Scholar 

  21. Catellani M, Destri S, Porzio W, Themans B, Bredas JL (1988) Thiazole-based polymers—synthesis, characterization and electronic-structure. Synth Met 26:259–265

    Article  CAS  Google Scholar 

  22. Sayyah SM, Kamal SM, Abd El-Rehim SS (2006) Electropolymerization of 2-amino-4-(4-methoxyphenyl)thiazole and characterization of the obtained polymer. Int J Polym Mater 55:79–101

    Article  CAS  Google Scholar 

  23. Bolognesi A, Catellani M, Destri S, Porzio W (1987) Polythiazole—a new semiconducting polymer having a heteroatom in the conduction pathway. Synth Met 18:129–132

    Article  CAS  Google Scholar 

  24. Yıldırım M, Kaya İ (2012) A comparative study of aminothiazole-based polymers synthesized by chemical oxidative polymerization. Synth Met 162:436–443

    Article  Google Scholar 

  25. Solmaz R, Kardaş G (2009) Electrochemical synthesis and characterization of poly-2-aminothiazole. Prog Org Coat 64:81–88

    Article  CAS  Google Scholar 

  26. Çiftçi H, Testereci HN, Öktem HN (2011) Electrochemical polymerization of 2-aminothiazole. Polym Bull 66:747–760

    Article  Google Scholar 

  27. Saggiomo V, Lüning U (2009) On the formation of imines in water—a comparison. Tetrahedron Lett 50:4663–4665

    Article  CAS  Google Scholar 

  28. Bilici A, Kaya İ, Yıldırım M (2010) Biosynthesis and characterization of organosoluble conjugated poly(2-aminofluorene) with the pyrazine bridged. Biomacromolecules 11:2593–2601

    Article  CAS  Google Scholar 

  29. Jablonski A (1933) Efficiency of anti-stokes fluorescence in dyes. Nature 131:839–840

    Article  CAS  Google Scholar 

  30. Diaz FR, Moreno J, Tagle LH, East GA, Radic D (1999) Synthesis, characterization and electrical properties of polyimines derived from selenophene. Synthetic Met 100:187–193

    Article  CAS  Google Scholar 

  31. Peng Y, Liu H, Zhang X, Li Y, Liu S (2009) CNT templated regioselective enzymatic polymerization of phenol in water and modification of surface of MWNT thereby. J Polym Sci, Part A: Polym Chem 47:1627–1635

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mehmet Yıldırım.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yıldırım, M., Kaya, İ. Synthesis and characterizations of poly(ether)/poly(phenol)s including azomethine coupled benzothiazole side chains: the effect of reaction conditions on the structure, optical, electrochemical, electrical and thermal properties. Polym. Bull. 71, 3067–3084 (2014). https://doi.org/10.1007/s00289-014-1238-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-014-1238-7

Keywords

Navigation