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Chemical Papers

, Volume 72, Issue 11, pp 2821–2832 | Cite as

Poly(azomethine-epoxy-ether) containing phenyl and etoxy moieties: synthesis, characterization and fluorescence property

  • Feyza KolcuEmail author
  • İsmet KayaEmail author
Original Paper
  • 136 Downloads

Abstract

The design and synthesis of poly(azomethine-epoxy-ether) (PAZ-EP) containing epoxide moiety was described. The purpose of the research was the improvement of poly(azomethine-ether) containing epoxide by introduction of Schiff base moiety. PAZ-EP was synthesized using epichlorohydrin (EP). The structure of the Schiff base (SB) and PAZ-EP were verified by FT-IR, 1H-NMR, 13C-NMR and UV–Vis spectroscopic analyses. Further characterization was employed using photophysical, electrochemical and fluorescence (PL) measurements. Application of TGA and differential scanning calorimetry analyses revealed thermal stability and thus propose a thermal processibility, which makes them potential materials for many contemporary practices. The number of average molecular weight of polymer with a polydispersity index of 1.14 was found to be 6750 Da using a gel permeation chromatography instrument. The highest occupied–lowest unoccupied energy levels and electrochemical (\(E_{\text{g}}^{'}\)) band gap values of PAZ-EP were determined by cyclic voltammetry (CV) measurement. Scanning electron microscopy (SEM) images were illustrated at different magnifications to study the morphologic property of PAZ-EP.

Keywords

Poly(azomethine-ether) Epichlorohydrin SEM Photoluminescence 

Notes

Acknowledgements

The authors thank Çanakkale Onsekiz Mart University scientific research project commission for support with the Project number (Project no.: FBA-2017-1135).

References

  1. Abid KK, Al-barody SM (2014) Synthesis, characterization and liquid crystalline behaviour of some lanthanides complexes containing two azobenzene Schiff base. Liq Cryst 41:1303–1314.  https://doi.org/10.1080/02678292.2014.919670 CrossRefGoogle Scholar
  2. Adams MC, Gannon JA (1986) Epoxy resins. In: Mark HF (ed) Encyclopedia of polymer science and engineering, 2nd edn. Wiley, New York, pp 322–382Google Scholar
  3. Barik S, Skene WG (2011) A fluorescent all-fluorene polyazomethine-towards soluble conjugated polymers exhibiting high fluorescence and electrochromic properties. Polym Chem 2:1091–1097.  https://doi.org/10.1039/c0py00394h CrossRefGoogle Scholar
  4. Bilici A, Kaya I, Yildirim M, Dogan F (2010) Enzymatic polymerization of hydroxy-functionalized carbazole monomer. J Mol Catal B Enzym 64:89–95.  https://doi.org/10.1016/j.molcatb.2010.02.007 CrossRefGoogle Scholar
  5. Bourgeaux M, Skene WG (2007) A highly conjugated p- and n-type polythiophenoazomethine: synthesis, spectroscopic, and electrochemical investigation. Macromolecules 40:1792–1795.  https://doi.org/10.1021/ma070292p CrossRefGoogle Scholar
  6. Cerrada P, Oriol L, Pinol M, Serrano JL (1996) Alternative synthetic strategies for Schiff base derived liquid crystal polymers: a comparative study. J Polym Sci Part A Polym Chem 34:2603–2611. https://doi.org/10.1002/(sici)1099-0518(19960930)34:13<2603::aid-pola6>3.0.CO;2-SGoogle Scholar
  7. Cervini R, Li XC, Spencer GWC, Holmes AB, Moratti SC, Friend RH (1997) Electrochemical and optical studies of PPV derivatives and poly(aromatic oxadiazoles). Synth Met 84:359–360CrossRefGoogle Scholar
  8. Choi EJ, Ahn JC, Chien LC, Lee CK, Zin WC, Kim DC, Shin ST (2004) Main chain polymers containing banana-shaped mesogens: synthesis and mesomorphic properties. Macromolecules 37:71–78.  https://doi.org/10.1021/ma0348122 CrossRefGoogle Scholar
  9. Colladet K, Nicolas M, Goris L, Lutsen L, Vanderzande D (2004) Low-band gap polymers for photovoltaic applications. Thin Solid Films 451:7–11.  https://doi.org/10.1016/j.tsf.2003.10.085 CrossRefGoogle Scholar
  10. Dutta PK, Jain P, Sen P, Trivedi R, Sen PK, Dutta J (2003) Synthesis and characterization of a novel polyazomethine ether for NLO application. Eur Polym J 39:1007–1011.  https://doi.org/10.1016/S0014-3057(02)00328-2 CrossRefGoogle Scholar
  11. Fukukawa K, Shibasaki Y, Ueda M (2004) Photosensitive poly(benzoxazole) via poly(o-hydroxy azomethine) II. Environmentally benign process in ethyl lactate. Polym J 36:489–494.  https://doi.org/10.1295/polymj.36.489 CrossRefGoogle Scholar
  12. Grigoras M, Antonoaia NC (2005) Synthesis and characterization of some carbazole-based imine polymers. Eur Polym J 41:1079–1089.  https://doi.org/10.1016/j.eurpolymj.2004.11.019 CrossRefGoogle Scholar
  13. Grigoras M, Catanescu CO (2004) Imine oligomers and polymers. J Macromol Sci Part C Polym Rev 44:131–173.  https://doi.org/10.1081/mc-120034152 CrossRefGoogle Scholar
  14. Grimm B, Krüger RP, Schrader S, Prescher D (2002) Molecular structure investigations on fluorine containing polyazomethines by means of the MALDI-TOF-MS technique. J Fluor Chem 113:85–91.  https://doi.org/10.1016/s0022-1139(01)00498-5 CrossRefGoogle Scholar
  15. Gul A, Akhter Z, Siddiq M, Qureshi R, Bhatti AS (2014) Synthesis and physicochemical characterization of poly(azomethine)esters containing aliphatic/aromatic moieties: electrical studies complemented by DFT calculation. J Appl Polym Sci 13:40698–40706.  https://doi.org/10.1002/app.40698 CrossRefGoogle Scholar
  16. Gutch PK, Banerjee S, Gupta DC, Jaiswal DK (2001) Poly-Schiff bases. V. Synthesis and characterization of novel soluble fluorine-containing polyether azomethines. J Polym Sci Part A Polym Chem 39:383–388.  https://doi.org/10.1002/1099-0518(20010201) CrossRefGoogle Scholar
  17. Hussein MA, Abdel-Rahman MA, Asiri AM, Alamry KA, Aly KI (2012) Review on: liquid crystalline polyazomethines polymers. Basics, syntheses and characterization. Des Monomers Polym 15:431–463.  https://doi.org/10.1080/1385772x.2012.688325 CrossRefGoogle Scholar
  18. Ishii J, Tanaka Y, Hasegawa M (2010) Film properties of polyazomethines (2). Poly(imide-azomethine)s derived from ester-containing dialdehydes, tetracarboxylic dianhydrides, and a fluorinated diamine. High Perform Polym 22:145–148.  https://doi.org/10.1177/0954008309349459 CrossRefGoogle Scholar
  19. Işık D, Santato C, Satyananda B, Skene WG (2012) Charge-carrier transport in thin films of π-conjugated thiopheno-azomethines. Org Electron 13:3022–3031.  https://doi.org/10.1016/j.orgel.2012.08.018 CrossRefGoogle Scholar
  20. Iwan A, Sek D (2008) Processible polyazomethines and polyketanils: from aerospace to light-emitting diodes and other advanced applications. Prog Polym Sci 33:289–345.  https://doi.org/10.1016/j.progpolymsci.2007.09.005 CrossRefGoogle Scholar
  21. Kaya I, Culhaoglu S (2009) Syntheses, structures and properties of novel oligo(azomethine ether)s containing or not chlorine atoms in the main chain. Polimery 54:266–274 (WOS: 000264697600005) Google Scholar
  22. Kaya I, Doğan F, Gül M (2011) A new Schiff base epoxy oligomer resin: synthesis, characterization, and thermal decomposition kinetics. J Appl Polym Sci 121:3211–3222.  https://doi.org/10.1002/app.33843 CrossRefGoogle Scholar
  23. Kaya İ, Ayten B, Şenol D (2018) Syntheses of poly(phenoxy-imine)s anchored with carboxyl group: characterization and photovoltaic studies. Opt Mater 78:421–431.  https://doi.org/10.1016/j.optmat.2018.02.057 CrossRefGoogle Scholar
  24. Kobzar YL, Tkachenko IM, Bliznyuk VN, Shekera OV, Turiv TM, Soroka PV, Nazarenko VG, Shevchenko VV (2016) Synthesis and characterization of fluorinated poly(azomethine ether)s from new core-fluorinated azomethine-containing monomers. Des Monomers Polym 19:1–11.  https://doi.org/10.1080/15685551.2015.1092007 CrossRefGoogle Scholar
  25. Kolcu F, Kaya I (2016) Synthesis and characterization of novel conjugated polyphenols of terephthaldehyde derived from symmetrical bis-azomethine groups in the polymer backbone via oxidative polycondensation. J Macromol Sci A 53:438–451.  https://doi.org/10.1080/10601325.2016.1176445 CrossRefGoogle Scholar
  26. Koole M, Frisenda R, Petrus ML, Perrin ML, van der Zant HSJ, Dingemans TJ (2016) Charge transport through conjugated azomethine-based single molecules for optoelectronic applications. Org Electron 34:38–41.  https://doi.org/10.1016/j.orgel.2016.03.043 CrossRefGoogle Scholar
  27. Krebs FC, Jørgensen M (2004) The effect of fluorination in semiconducting polymers of the polyphenyleneimine type. Synth Met 142:181–185.  https://doi.org/10.1016/j.synthmet.2003.08.015 CrossRefGoogle Scholar
  28. Kumar S, Dhar DN, Saxena P (2009) Applications of metal complexes of Schiff bases—a review. J Sci Ind Res 68:181–187 (WOS: 000264035600001) Google Scholar
  29. Liu W, Lee SH, Yang SZ, Bian SP, Li L, Samuelson LA, Kumar J, Tripathy SK (2001) Biologically derived photoactive macromolecular azodyes. J Macromol Sci Pure Appl Chem 38:1355–1370.  https://doi.org/10.1081/ma-100108390 CrossRefGoogle Scholar
  30. Liu P, Wu YL, Pan HL, Li YN, Gardner S, Ong BS, Zhu SP (2009) Novel high-performance liquid-crystalline organic semiconductors for thin-film transistors. Chem Mater 21:2727–2732.  https://doi.org/10.1021/cm900265q CrossRefGoogle Scholar
  31. Ma BB, Zhang H, Wang Y, Peng W, Wang MK, Shen Y (2015) Visualized acid–base discoloration and optoelectronic investigations of azines and azomethines having double 4-[N,N-di(4-methoxyphenyl)amino]phenyl terminals. J Mater Chem C 3:7748–7755.  https://doi.org/10.1039/c5tc00909j CrossRefGoogle Scholar
  32. Marin L, Cozan V, Bruma M, Grigoras VC (2006) Synthesis and thermal behaviour of new poly(azomethine-ether). Eur Polym J 42:1173–1182.  https://doi.org/10.1016/j.eurpolymj.2005.11.010 CrossRefGoogle Scholar
  33. Marin L, Bejan A, Ailincai D, Belei D (2017) Poly(azomethine-phenothiazine)s with efficient emission in solid state. Eur Polymer J 95:127–137.  https://doi.org/10.1016/j.eurpolymj.2017.08.006 CrossRefGoogle Scholar
  34. Nitschke P, Jarząbek B, Wanic A, Domański M, Hajduk B, Janeczek H, Kaczmarczyk B, Musioł M, Kawalec M (2017) Effect of chemical structure and deposition method on optical properties of polyazomethines with alkyloxy side groups. Synth Met 232:171–180.  https://doi.org/10.1016/j.synthmet.2017.08.011 CrossRefGoogle Scholar
  35. Niu HJ, Kang HQ, Cai JW, Wang C, Bai HD, Wang W (2011) Novel soluble polyazomethines with pendant carbazole and triphenylamine derivatives: preparation, characterization, and optical, electrochemical and electrochromic properties. Polym Chem 2:2804–2817.  https://doi.org/10.1039/c1py00237f CrossRefGoogle Scholar
  36. Park Y, Lee JH, Jung DH, Liu SH, Lin YH, Chen LY, Wud CC, Park J (2010) An aromatic imine group enhances the EL efficiency and carrier transport properties of highly efficient blue emitter for OLEDs. J Mater Chem 20:5930–5936.  https://doi.org/10.1039/c0jm00581a CrossRefGoogle Scholar
  37. Pron A, Rannou P (2002) Processible conjugated polymers: from organic semiconductors to organic metals and superconductors. Prog Polym Sci 27:135–190.  https://doi.org/10.1016/s0079-6700(01)00043-0 CrossRefGoogle Scholar
  38. Qu L, Shi G (2004) Crystalline oligopyrene nanowires with multicolored emission. Chem Commun 24:2800–2801.  https://doi.org/10.1039/b412638f CrossRefGoogle Scholar
  39. Ravikumar L, Kalaivani S, VidhyadeviT Murugasen A, Kirupha SD, Sivanesan S (2014) Synthesis, characterization and metal ion adsorption studies on novel aromatic poly(azomethine amide)s containing thiourea groups. Open J Polym Chem 4:1–11.  https://doi.org/10.4236/ojpchem.2014.41001 CrossRefGoogle Scholar
  40. Saegusa Y, Sekiba K, Nakamura S (1990) Synthesis and characterization of novel 1,3,4-oxadiazole-containing or 1,3,4-thiadiazole-containing wholly conjugated polyazomethines. J Polym Sci Part A Polym Chem 28:3647–3659.  https://doi.org/10.1002/pola.1990.080281311 CrossRefGoogle Scholar
  41. Saegusa Y, Kuriki M, Nakamura S (1994) Preparation and characterization of fluorine-containing aromatic condensation polymers, 4.Preparation and characterization of fluorine-containing aromatic polyazomethines and copolyazomethines from perfluoroisopropylidene group-containing aromatic diamines and/or isopropylidene group-containing aromatic diamines and phthaladehydes. Macromol Chem Phys 195:1877–1889.  https://doi.org/10.1002/macp.1994.021950535 CrossRefGoogle Scholar
  42. Sek D, Iwan A, Jarzabek B, Kaczmarczyk B, Kasperczyk J, Mazurak Z, Domanski M, Karon M, Lapkowski M (2008) Hole transport triphenylamine–azomethine conjugated system: synthesis and optical, photoluminescence, and electrochemical properties. Macromolecules 41:6653–6663.  https://doi.org/10.1021/ma702637k CrossRefGoogle Scholar
  43. Shukla U, Rao KV, Rakshit AK (2003) Thermotropic liquid-crystalline polymers: synthesis, characterization, and properties of poly(azomethine esters). J Appl Polym Sci 88:153–160.  https://doi.org/10.1002/app.11618 CrossRefGoogle Scholar
  44. Stefanache A, Balan M, Harabagiu V, Aubert PH, Guegan P, Farcas A (2014) Electro-optical properties of aromatic oligoazomethine/permethylated alpha-cyclodextrin main-chain polyrotaxanes. Chem Phys Lett 599:104–109.  https://doi.org/10.1016/j.cplett.2014.03.027 CrossRefGoogle Scholar
  45. Vaganova E, Rozenberg M, Yitzchaik S (2000) Multicolor emission in poly(4-vinyl-pyridine). Gel Chem Mater 12:261–263.  https://doi.org/10.1021/cm990480x CrossRefGoogle Scholar
  46. Yeh LC, Huang TC, Lai FY, Lai HG, Lo AY, Hsu SC, Yang TI, Yeh JM (2016) Synthesis of electroactive polyazomethine and its application in electrochromic property and electrochemical sensor. Surf Coat Technol 303:154–161.  https://doi.org/10.1016/j.surfcoat.2016.03.094 CrossRefGoogle Scholar
  47. Zhang WB, Wang C, Liu G, Wang J, Chen Y, Li RW (2014) Structural effect on the resistive switching behavior of triphenylamine-based poly(azomethine)s. Chem Commun 50:11496–11499.  https://doi.org/10.1039/c4cc05233a CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Polymer Synthesis and Analysis LaboratoryÇanakkale Onsekiz Mart UniversityÇanakkaleTurkey
  2. 2.Department of Chemistry and Chemical Processing Technologies, Lapseki Vocational SchoolÇanakkale Onsekiz Mart UniversityÇanakkaleTurkey

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