Skip to main content
Log in

Comparative study on oxidative and enzyme catalyzed oxidative polymerization of aminophenol compound containing dihalogen

  • ORIGINAL PAPER
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Properties of polymers were obtained by enzyme catalyzed oxidative polymerization varies according to oxidative polymerization products and thus polymeric materials with different properties are obtained. In this study, polymerization of 4-amino-2,6-dichlorophenol (ADCP), an aminophenol compound containing dihalogen, was carried out by two different methods and the two methods were compared with each other. One of the methods was oxidative polymerization in the presence of hydrogen peroxide with heating, and the other was enzyme-catalyzed oxidative polymerization that took place at room temperature in the presence of Horse Radish Peroxidase (HRP) enzyme and hydrogen peroxide. The structural characterization of the products obtained as a result of oxidative polymerization (PADCP-O) and as a result of enzyme catalyzed oxidative polymerization (PADCP-E) was performed by 1H-NMR, 13C-NMR, FT-IR, UV–Vis spectroscopy methods. The molecular masses of PADCP-O and PADCP-E were analyzed by GPC and the average molecular mass of PADCP-E was found to be higher than that of PADCP-O. Thermal properties were examined by TGA and it was determined that the thermal stability of the obtained polymers was higher than that of the monomer. Electrochemical and optical properties were determined by CV and UV–Vis spectroscopy methods, respectively. Electrochemical and optical band gap values were calculated as 1.61 and 1.33 eV, and 1.88 and 1.83 eV for PADCP-O and PADCP-E, respectively. In addition, it was observed that PADCP-O emitted green in UV light, while PADCP-E emitted red in DMSO. Surface properties and morphology of polymers were analyzed by SEM and it was observed that PADCP-O obtained by oxidative polymerization had a spongy structure, but the enzymatic polymerization product PADCP-E had a uniformly dispersed nanoparticle structure.

Graphical abstract

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
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Kobayashi S, Uyama H, Kimura S (2001) Enzymatic polymerization. Chem Rev 101:3793–3818. https://doi.org/10.1021/cr990121l

    Article  CAS  PubMed  Google Scholar 

  2. Bilici A, Kaya I, Yildirim M, Doĝan 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

    Article  CAS  Google Scholar 

  3. Li XG, Huang MR, Yang Y (2001) Synthesis and characterization of o-phenylenediamine and xylidine copolymers. Polymer (Guildf) 42:4099–4107. https://doi.org/10.1016/S0032-3861(00)00661-3

    Article  CAS  Google Scholar 

  4. Rawat B, Kansara SS, Rama HS (1991) Synthesis and study of thermal and electrical behaviour of some polyaromatic amines. Polym Int 26:233–238. https://doi.org/10.1002/pi.4990260406

    Article  CAS  Google Scholar 

  5. Wei Y, Jang GW, Chan CC et al (1990) Polymerization of aniline and alkyl ring-substituted anilines in the presence of aromatic additives. J Phys Chem 94:7716–7721. https://doi.org/10.1021/j100382a073

    Article  CAS  Google Scholar 

  6. Yamaguchi I, Yamamoto T (2003) Enzymatic polymerization of a ferrocenophane to give poly(oxyphenylene) with ferrocenophane pendant groups. Inorganica Chim Acta 348:249–253. https://doi.org/10.1016/S0020-1693(02)01470-6

    Article  CAS  Google Scholar 

  7. Karayigitoglu CF, Kommareddi N, Gonzalez RD et al (1995) The morphology of phenolic polymers enzymatically synthesized in surfactant microstructures. Mater Sci Eng C 2:165–171. https://doi.org/10.1016/0928-4931(95)00058-5

    Article  Google Scholar 

  8. Kobayashi S, Makino A (2009) Enzymatic polymer synthesis: an opportunity for green polymer chemistry. Chem Rev 109:5288–5353. https://doi.org/10.1021/cr900165z

    Article  CAS  PubMed  Google Scholar 

  9. Reihmann M, Ritter H (2006) Synthesis of phenol polymers using peroxidases. Adv Polym Sci 194:1–49. https://doi.org/10.1007/12_034

    Article  CAS  Google Scholar 

  10. Dordick JS (1992) Enzymatic and Chemoenzymatic Approaches to Polymer Synthesis and Modification. Ann N Y Acad Sci 672:352–362. https://doi.org/10.1111/j.1749-6632.1992.tb35645.x

    Article  CAS  PubMed  Google Scholar 

  11. Kim J, Wu X, Herman MR, Dordick JS (1998) Enzymatically generated polyphenols as array-based metal-ion sensors. Anal Chim Acta 370:251–258. https://doi.org/10.1016/S0003-2670(98)00292-X

    Article  CAS  Google Scholar 

  12. Dordick JS, Marletta MA, Klibanov AM (1987) Polymerization of phenols catalyzed by peroxidase in nonaqueous media. Biotechnol Bioeng 30:31–36. https://doi.org/10.1002/bit.260300106

    Article  CAS  PubMed  Google Scholar 

  13. Oguchi T, Tawaki S, Uyama H, Kobayashi S (1999) Soluble polyphenol. Macromol Rapid Commun 20:401–403. https://doi.org/10.1002/(sici)1521-3927(19990701)20:7%3c401::aid-marc401%3e3.3.co;2-y

    Article  CAS  Google Scholar 

  14. Kurioka H, Komatsu I, Uyama H, Kobayashi S (1994) Enzymatic oxidative polymerization of alkylphenols. Macromol Rapid Commun 15:507–510. https://doi.org/10.1002/marc.1994.030150609

    Article  CAS  Google Scholar 

  15. Uyama H, Kurioka H, Sugihara J et al (1997) Oxidative polymerization of p-Alkylphenols catalyzed by horseradish peroxidase. J Polym Sci Part A Polym Chem 35:1453–1459. https://doi.org/10.1002/(SICI)1099-0518(199706)35:8%3c1453::AID-POLA14%3e3.0.CO;2-6

    Article  CAS  Google Scholar 

  16. Neoh KG, Kang ET, Tan KL (1992) Structural investigations of aromatic amine polymers. J Phys Chem 96:6777–6783. https://doi.org/10.1021/j100195a046

    Article  CAS  Google Scholar 

  17. Mezhuev YO, Korshak YV, Shtilman MI (2017) Oxidative polymerization of aromatic amines: kinetic features and possible mechanisms. Russ Chem Rev 86:1271–1285. https://doi.org/10.1070/rcr4755

    Article  CAS  Google Scholar 

  18. Kahovec J (1988) Simple synthesis of polymeric primary aromatic amines. Polym Bull 50:43–50

    Google Scholar 

  19. Taj S, Ahmed MF, Sankarapapavinasam S (1992) Poly(para-aminophenol): a new soluble, electroactive conducting polymer. J Electroanal Chem 338:347–352. https://doi.org/10.1016/0022-0728(92)80433-5

    Article  CAS  Google Scholar 

  20. Taj S, Ahmed MF, Sankarapapavinasam S (1992) Electro-oxidative polymerization of m-aminophenol. Synth Met 52:147–158. https://doi.org/10.1016/0379-6779(92)90303-Z

    Article  CAS  Google Scholar 

  21. Kaya İ, Kolcu F (2018) Polymerization of Chrysoidine with chemical and enzymatic oxidative preference: Synthesis, characterization, and spectroscopic study. Polym Adv Technol 29:2515–2528. https://doi.org/10.1002/pat.4363

    Article  CAS  Google Scholar 

  22. Ćirić-Marjanović G, Milojević-Rakić M, Janošević-Ležaić A et al (2017) Enzymatic oligomerization and polymerization of arylamines: State of the art and perspectives. Chem Pap 71:199–242. https://doi.org/10.1007/s11696-016-0094-3

    Article  CAS  Google Scholar 

  23. Kolcu F (2019) Characterization and spectroscopic study of enzymatic oligomerization of phenazopyridine hydrochloride. J Mol Struct 1188:76–85. https://doi.org/10.1016/j.molstruc.2019.03.083

    Article  CAS  Google Scholar 

  24. Cheng YJ, Yang SH, Hsu CS (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868–5923. https://doi.org/10.1021/cr900182s

    Article  CAS  PubMed  Google Scholar 

  25. Li H, Bai J, Shi Z, Yin J (2016) Environmental friendly polymers based on schiff-base reaction with self-healing, remolding and degradable ability. Polymer (Guildf) 85:106–113. https://doi.org/10.1016/j.polymer.2016.01.050

    Article  CAS  Google Scholar 

  26. Kolcu F, Kaya İ (2020) A study of the chemical and the enzyme-catalyzed oxidative polymerization of aromatic diamine bearing chlor substituents, pursuant to structural, thermal and photophysical properties. Eur Polym J 133. https://doi.org/10.1016/j.eurpolymj.2020.109767

  27. Kaya I, Karaer H (2020) Synthesis and characterization of poly(3,5-diaminobenzoic acid) via enzymatic and oxidative polymerization and application in methylene blue adsorption. J Mol Struct 1216:122383. https://doi.org/10.1016/j.ygyno.2016.04.081

    Article  Google Scholar 

  28. Temizkan K, Kaya İ (2020) Fluorescence quantum yields and chromatic properties of poly(azomethine)s containing pyridine ring. Mater Sci Eng B Solid-State Mater Adv Technol 252. https://doi.org/10.1016/j.mseb.2019.114483

  29. Ashokkumar SP, Vijeth H, Yesappa L et al (2020) Electrochemically synthesized polyaniline/copper oxide nano composites: To study optical band gap and electrochemical performance for energy storage devices. Inorg Chem Commun 115:107865. https://doi.org/10.1016/j.inoche.2020.107865

    Article  CAS  Google Scholar 

  30. Igawa S, Hashimoto M, Kawata I et al (2013) Highly efficient green organic light-emitting diodes containing luminescent tetrahedral copper(i) complexes. J Mater Chem C 1:542–551. https://doi.org/10.1039/c2tc00263a

    Article  CAS  Google Scholar 

  31. Kaya İ, Kılavuz E, Temizkan K (2020) Synthesis, characterization and quantum yields of multichromic poly(azomethine)s containing carbazole unit. Arab J Chem 13:1335–1344. https://doi.org/10.1016/j.arabjc.2017.11.004

    Article  CAS  Google Scholar 

  32. Miwa T, Kubo S, Shizu K et al (2017) Blue organic light-emitting diodes realizing external quantum efficiency over 25% using thermally activated delayed fluorescence emitters. Sci Rep 7:1–8. https://doi.org/10.1038/s41598-017-00368-5

    Article  CAS  Google Scholar 

  33. Chen CT (2004) Evolution of red organic light-emitting diodes: Materials and devices. Chem Mater 16:4389–4400. https://doi.org/10.1021/cm049679m

    Article  CAS  Google Scholar 

  34. Wu WC, Yeh HC, Chan LH, Chen CT (2002) Red organic light-emitting diodes with a non-doping amorphous red emitter. Adv Mater 14:1072–1075. https://doi.org/10.1002/1521-4095(20020805)14:15%3c1072::AID-ADMA1072%3e3.0.CO;2-Z

    Article  CAS  Google Scholar 

  35. Liu X, Yao B, Zhang Z et al (2016) Power-efficient solution-processed red organic light-emitting diodes based on an exciplex host and a novel phosphorescent iridium complex. J Mater Chem C 4:5787–5794. https://doi.org/10.1039/c6tc01270a

    Article  CAS  Google Scholar 

  36. Kurioka H, Uyama H, Kobayashi S (1998) Peroxidase-catalyzed dispersion polymerization of phenol derivatives. Polym J 30:526–529. https://doi.org/10.1295/polymj.30.526

    Article  CAS  Google Scholar 

  37. Uyama H, Kurioka H, Kobayashi S (1999) Preparation of polyphenol particles by peroxidase-catalyzed dispersion polymerization. Colloids Surfaces A Physicochem Eng Asp 153:189–194. https://doi.org/10.1016/S0927-7757(98)00442-7

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to İsmet Kaya.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaya, İ., Yeldir, E.K. Comparative study on oxidative and enzyme catalyzed oxidative polymerization of aminophenol compound containing dihalogen. J Polym Res 28, 365 (2021). https://doi.org/10.1007/s10965-021-02733-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-021-02733-5

Keywords

Navigation