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.
Similar content being viewed by others
References
Kruger H, Janietz S, Sainova D, Wedel A (2003) New organo-soluble conjugated polyquinolines. Macromol Chem Phys 204:1607–1615
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
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
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
Barik S, Bletzacker T, Skene WG (2012) Pi-conjugated fluorescent azomethine copolymers: opto-electronic, halochromic, and doping properties. Maromolecules 45:1165–1173
Adhikari B, Majumdar S (2004) Polymers in sensor applications. Prog Polym Sci 29:699–766
Bai H, Shi G (2007) Gas sensors based on conducting polymers. Sensors-Basel 7:267–307
Ragimov AV, Mamedov BA, Gasanova SG (1997) New efficient dielectric and antistatic materials based on oligoaminophenols. Polym Int 43:343–346
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
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
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
Bilici A, Kaya İ, Şenol D (2011) Phenol side-groups-containing fluorene polymer synthesized by catalytic oxidative polymerization. Polym Advan Technol 22:1953–1958
Bilici A, Kaya İ, Yıldırım M, Doğan F (2010) Enzymatic polymerization of hydroxy-functionalized carbazole monomer. J Mol Catal B: Enzymatic 64:89–95
Bilici A, Kaya İ, Yıldırım M (2011) Peroxidase-catalyzed synthesis of polyphenols bearing aldehyde units. Des Monomers Polym 14:353–366
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
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
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
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
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
Maruyama T, Suganuma H, Yamamoto T (1995) Preparation of pi-conjugated polythiazoles and their electrically conducting properties. Synth Met 74:183–185
Catellani M, Destri S, Porzio W, Themans B, Bredas JL (1988) Thiazole-based polymers—synthesis, characterization and electronic-structure. Synth Met 26:259–265
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
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
Yıldırım M, Kaya İ (2012) A comparative study of aminothiazole-based polymers synthesized by chemical oxidative polymerization. Synth Met 162:436–443
Solmaz R, Kardaş G (2009) Electrochemical synthesis and characterization of poly-2-aminothiazole. Prog Org Coat 64:81–88
Çiftçi H, Testereci HN, Öktem HN (2011) Electrochemical polymerization of 2-aminothiazole. Polym Bull 66:747–760
Saggiomo V, Lüning U (2009) On the formation of imines in water—a comparison. Tetrahedron Lett 50:4663–4665
Bilici A, Kaya İ, Yıldırım M (2010) Biosynthesis and characterization of organosoluble conjugated poly(2-aminofluorene) with the pyrazine bridged. Biomacromolecules 11:2593–2601
Jablonski A (1933) Efficiency of anti-stokes fluorescence in dyes. Nature 131:839–840
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
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
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-014-1238-7