Skip to main content
SpringerLink
Log in

Synthesis, Electrochemical and Fluorescence Properties of Poly(azomethine-naphthalene)s

  • Research Article - Chemistry
  • Published:
Arabian Journal for Science and Engineering Aims and scope Submit manuscript

Abstract

In this study, novel types of poly(azomethine-naphthalene)s were synthesized containing naphthalene unit along the main chain in two steps. In the first step, symmetrical Schiff base diols that contain naphthalene unit in center and in the second step, poly(azomethine-naphthalene)s expanding with C–C coupling were obtained by elimination and oxidative polycondensation reactions, respectively. These purely synthesized compounds were characterized by UV–Vis, FT-IR, \(^{1}\hbox {H-NMR}\) and \(^{13}\hbox {C-NMR}\) analyses, and also their electrochemical, thermal, photonic and surface properties were illuminated by cyclic voltammetry (CV), thermogravimetric analysis, differential thermal analysis, differential scanning calorimetry, photoluminescence and scanning electron microscopy analysis techniques. According to TG analysis, char % amounts of P-2HBAN, P-2HNAN, P-4HBAN and P-3H4MBAN were found to be 9.3, 18.0, 66.6 and 47.1, respectively, at \(1000\, ^{\circ }\hbox {C}\). Also, these compounds have glass transition temperature \(({T}_{\mathrm{g}})\) higher than \(127\,^{\circ }\hbox {C}\) and onset temperature higher than \(153 \,^{\circ }\hbox {C}\). For this reason, they are useful for the production of thermal-resistant materials. In addition, electrochemical and fluorescence properties of all the compounds were examined by CV and fluorescence spectrophotometer measurements, respectively.

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

Similar content being viewed by others

References

  1. Doğan, F.; Temizkan, K.; Kaya, İ.: A novel shape-controlled synthesis of bifunctional organic polymeric nanoparticles. Polymer 70, 59–67 (2015)

    Article  Google Scholar 

  2. Hsiao, S.H.; Lin, S.W.: Electrochemical synthesis of electrochromic polycarbazole films from \(N\)-phenyl-3,6-bis(\(N\)-carbazolyl)carbazoles. Polym. Chem. 7, 198–211 (2016)

    Article  Google Scholar 

  3. Figueira-Duarte, T.M.; Rosso, P.G.D.; Trattnig, R.; Sax, S.; List, E.J.W.; Müllen, K.: Designed suppression of aggregation in polypyrene: toward high-performance blue-light-emitting diodes. Adv. Mater. 22, 990–993 (2010)

    Article  Google Scholar 

  4. Simas, E.R.; Martins, T.D.; Atvars, T.D.Z.; Akcelrud, L.: Synthesis and photophysical properties of a novel soluble polyquinoline. J. Lumin. 129, 119–125 (2009)

    Article  Google Scholar 

  5. Göktaş, H.; Demircioglu, Z.; Sel, K.; Gunes, T.; Kaya, İ.: The optical properties of plasma polymerized polyaniline thin films. Thin Solid Films 548, 81–85 (2013)

    Article  Google Scholar 

  6. Bilici, A.; Geçibesler, İ.H.; Kaya, İ.: Enzymatic synthesis of 5-amino quinoline oligomers and evaluation of their free radical scavenging activity. Can. J. Chem. Reveu Can. Chim. 95, 7–15 (2017)

    Article  Google Scholar 

  7. Alphonse, R.; Varghese, A.; George, L.; Nizam, A.: Estimation of ground state and excited state dipole moments of a novel Schiff base derivative containing 1, 2, 4-triazole nucleus by solvatochromic method. J. Mol. Liq. 215, 387–395 (2016)

    Article  Google Scholar 

  8. Doğan, F.; Kaya, İ.; Temizkan, K.: Synthesis route to region selectively functionalized bifunctional polyarene. Polym. Int. 64, 1639–1648 (2015)

    Article  Google Scholar 

  9. Sood, R.; Donnadio, A.; Giancola, S.; Kreisz, A.; Jones, D.J.; Cavaliere’, S.: 1,2,3-Triazole-functionalized polysulfone synthesis through microwave-assisted copper-catalyzed click chemistry: a highly proton conducting high temperature membrane. ACS Appl. Mater. Interfaces 8, 16897–16906 (2016)

    Article  Google Scholar 

  10. Bilici, A.; Ayten, B.; Kaya, İ.: Facile preparation of gold nanoparticles on the polyquinoline matrix: catalytic performance towards 4-nitrophenol reduction. Synth. Met. 201, 11–17 (2015)

    Article  Google Scholar 

  11. Doğan, F.; Kaya, İ.; Temizkan, K.: Template-free oxidative synthesis of polyaminonaphthol nanowires. Eur. Polym. J. 66, 397–406 (2015)

    Article  Google Scholar 

  12. Avci, A.; Temizkan, K.; Kaya, İ.: Fluorescence, thermal and electrochemical properties of poly(azomethine-urethane)s containing sulfone group. Polym. Bull. 72, 2871–2889 (2015)

    Article  Google Scholar 

  13. Karaer, H.; Kaya, İ.: Synthesis, characterization, and thermal decompositions of Schiff base polymers containing chitosan unit. Iran. Polym. J. 24, 471–480 (2015)

    Article  Google Scholar 

  14. Kaya, İ.; Avcı, A.; Kolcu, F.; Çulhaoğlu, S.: Synthesis, characterization, optical, and electrochemical properties of thermal stable novel poly(azomethine-ether)s. Des. Monomers Polym. 17, 481–490 (2014)

    Article  Google Scholar 

  15. Kaya, İ.; Bora, E.; Aydin, A.: Synthesis and characterization of Schiff base derivative with pyrrole ring and electrochromic applications of its oligomer. Prog. Org. Coat. 77, 463–472 (2014)

    Article  Google Scholar 

  16. Kaya, İ.; Bilici, A.; Tezel, R.N.; Temizkan, K.; Doğan, F.: Peroxidase/\(\text{ H }_{{2}}\text{ O }_{2}\) catalyzed oxidative oligomerization of 1-aminopyrene. J. Macromol. Sci. Part A Pure Appl. Chem. 54, 243–248 (2017)

    Article  Google Scholar 

  17. Bilici, A.; Doğan, F.; Yildirim, M.; Kaya, İ.: Facile and region selective synthesis of poly(5-hydroxyquinoline). React. Funct. Polym. 71, 675–683 (2011)

    Article  Google Scholar 

  18. Şenol, D.; Kaya, İ.: Synthesis and characterizations of poly(phenoxy-imine)s via catalyzed oxidative polymerization by polymer-metal complex. Arab. J. Sci. Eng. 42, 2381–2396 (2017)

    Article  Google Scholar 

  19. Li, X.G.; Feng, H.; Huang, M.R.; Gu, G.L.; Moloney, M.G.: Ultrasensitive Pb(II) potentiometric sensor based on copolyaniline nanoparticles in a plasticizer-free membrane with a long lifetime. Anal. Chem. 84, 134–140 (2012)

    Article  Google Scholar 

  20. Huang, M.R.; Peng, Q.Y.; Li, X.G.: Rapid and effective adsorption of lead ions on fine poly(phenylenediamine) microparticles. Chem. A Eur. J. 12(16), 4341–4350 (2006)

    Article  Google Scholar 

  21. Huang, M.R.; Ding, Y.B.; Li, X.G.; Liu, Y.; Xi, K.; Gao, C.L.; Kumar, R.V.: Synthesis of semiconducting polymer microparticles as solid ionophore with abundant complexing sites for long-life Pb(II) sensors. ACS Appl. Mater. Interfaces 6, 22096–22107 (2014)

    Article  Google Scholar 

  22. Li, X.G.; Liao, Y.; Huang, M.R.; Strong, V.; Kaner, R.B.: Ultra-sensitive chemosensors for Fe(III) and explosives based on highly fluorescent oligofluoranthene. Chem. Sci. 4, 1970–1978 (2013)

    Article  Google Scholar 

  23. Li, X.G.; Liu, R.; Huang, M.R.: Facile synthesis and highly reactive silver ion adsorption of novel microparticles of sulfodiphenylamine and diaminonaphthalene copolymers. Chem. Mater. 17, 5411–5419 (2005)

    Article  Google Scholar 

  24. Li, X.G.; Ma, X.L.; Sun, J.; Huang, M.R.: Powerful reactive sorption of silver (I) and mercury (II) onto poly(\(o\)-phenylenediamine) microparticles. Langmuir 25, 1675–1684 (2009)

    Article  Google Scholar 

  25. Temizkan, K.; Kaya, İ.: Synthesis, characterization, electrochemical and surface morphology properties of poly(azomethine-ester)s. Polym. Bull. 74, 2575–2592 (2017)

    Article  Google Scholar 

  26. Ahamad, T.; Alshehri, S.M.: Thermal, microbial, and corrosion resistant metal-containing poly(Schiff) epoxy coatings. J. Coat. Technol. Res. 9, 515–523 (2012)

    Article  Google Scholar 

  27. Zhang, L.; Huang, X.H.; Hu, J.S.; Song, J.; Kim, I.: A hyper-cross-linked polynaphthalene semiconductor with excellent visible-light photo catalytic performance in the degradation of organic dyes. Langmuir 33, 1867–1871 (2017)

    Article  Google Scholar 

  28. Kolcu, F.; Kaya, İ.: Synthesis and characterization of conjugated polyphenols derived from azomethine formation containing terephtaldehyde via oxidative polycondensation. J. Macromol. Sci. Part A Pure Appl. Chem. 53(7), 438–451 (2016)

    Article  Google Scholar 

  29. Ramírez, J.R.; Ruiz-Carretero, A.; Herrero, M.A.; Sanchez-Migallon, A.; Hoz, A.: Green synthesis of luminescent blue emitters based on bistriazines with naphthalene as a p-conjugated spacer. Dyes Pigments 124, 203–209 (2016)

    Article  Google Scholar 

  30. Zheng, Y.; Zheng, J.; Wu, C.; Shang, X.; Lin, J.: Blue-emitting poly(1,10-binaphthol butyl ether) nanospheres via the nonsolvent vapor method. Polym. Bull. 73, 2843–2854 (2016)

    Article  Google Scholar 

  31. Elbasri, M.; Majid, S.; Rhazi, M.E.: Highly improved electrocatalytic oxidation of methanol on poly(1,5-diaminonaphthalene)/nickel nanoparticles film modified carbon nanofiber. J. Mater. Environ. Sci. 8, 2860–2869 (2017)

    Google Scholar 

  32. Hsiao, S.H.; Han, J.S.: Solution-processable trans-missive-to-green switching electrochromic polyamides bearing 2,7-bis(diphenylamino) naphthalene units. J. Polym. Sci. Part A Polym. Chem. 55, 1409–1421 (2017)

    Article  Google Scholar 

  33. Osada, I.; Vries, H.; Scrosati, B.; Passerini, S.: Ionic-liquid-based polymer electrolytes for battery. Angew. Chem. Int. Ed. 55, 500–513 (2016)

    Article  Google Scholar 

  34. Castell, P.; Serra, A.; Galia, M.: New liquid-crystalline thermosets from liquid-crystalline bisazomethynic epoxy resins with naphthalene disruptors in the central core. J. Polym. Sci. Part A Polym. Chem. 41, 1536–1544 (2003)

    Article  Google Scholar 

  35. Ma, C.; Chen, X.; Long, D.; Wang, J.; Qiao, W.; Ling, L.: High-surface-area and high-nitrogen-content carbon microspheres prepared by a pre-oxidation and mild KOH activation for superior super capacitor. Carbon 118, 699–708 (2017)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Polymer Synthesis and Analysis Laboratory, Department of Chemistry, Çanakkale Onsekiz Mart University, 17020, Çanakkale, Turkey

    İsmet Kaya & Fatma Zehra Yener

Authors
  1. İsmet Kaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fatma Zehra Yener
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to İsmet Kaya.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaya, İ., Yener, F.Z. Synthesis, Electrochemical and Fluorescence Properties of Poly(azomethine-naphthalene)s. Arab J Sci Eng 44, 6339–6349 (2019). https://doi.org/10.1007/s13369-019-03777-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13369-019-03777-y

Keywords

Search

Navigation