Abstract
Polyphenols containing Schiff base pendent groups, poly(4-[benzylidene-amino]-phenol) (PBP), and poly(4-[(anthracen-9-ylmethylene)-amino]-phenol) (PAP) have been synthesized through the combination of Schiff base reaction and enzymatic polymerization using horseradish peroxidase (HRP) as catalyst. The polymers were characterized by GPC, FTIR, 1H NMR, and UV spectroscopy. It shows that PBP and PAP are composed of polyphenol main chains bearing Schiff base pendent side groups. The PBP exhibits better solubility than PAP in some common solvents. The PAP has a large red-shift of 86 nm compared with polyphenols, indicating the Schiff base pendent groups remarkably increase the conjugation lengths of polyphenols.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Sch1_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Fig1_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Sch2_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Fig2_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Fig3_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Fig4_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Fig5_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs00289-009-0163-7/MediaObjects/289_2009_163_Fig6_HTML.gif)
Similar content being viewed by others
References
Ayyagari MS, Marx KA, Tripathy SK, Akkara JA, Kaplan DL (1995) Controlled free-radical polymerization of phenol derivatives by enzyme-catalyzed reactions in organic solvents. Macromolecules 28:5192–5197
Barbero C, Silber JJ, Sereno LJ (1989) Formation of a novel electroactive film by electropolymerization of ortho-aminophenol: study of its chemical structure and formation mechanism. Electropolymerization of analogous compounds. Electroanal Chem 263:333–352
Kunimura S, Ohsaka T, Oyama N (1988) Preparation of thin polymeric films on electrode surfaces by electropolymerization of o-aminophenol. Macromolecules 21:894–900
Taj S, Ahmed MF, Sankarapapavinasam S (1992) Poly(para-aminophenol): a new soluble, electroactive conducting polymer. J Electroanal Chem 338:347–352
Sankarapapavinasam S (1993) Kinetics and mechanism of electropolymerization of m-aminophenol. J Polym Sci Part A Polym Chem 31:1105–1109
Dordick JS, Marletta MA, Kilbanov AM (1987) Polymerization of phenols catalyzed by peroxidase in nonaqueous media. Biotechnol Bioeng 30:31–36
Premachandran RS, Banerjee S, Wu XK, John VT, McPherson GL, Akkara J, Ayyagari M, Kaplan D (1996) Enzymatic synthesis of fluorescent naphthol-based polymers. Macromolecules 29:6452–6460
Xu P, Kumar J, Samuelson L, Cholli AL (2002) Monitoring the enzymatic polymerization of 4-phenylphenol by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: a novel approach. Biomacromolecules 3:889–893
Liu W, Bian S, Li L, Samuelson L, Kumar J, Tripathy S (2000) Enzymatic synthesis of photoactive poly(4-phenylazophenol). Chem Mater 12:1577–1584
Gross RA, Kaplan DL, Swift G (eds) (1998) Enzymes in polymer science. In: Enzymes in polymer synthesis, ACS Sympoium Series No 684. American Chemical Society, Washington DC
Kobayashi S, Shoda S, Uyama H (1996) Enzymatic polymerization. In: Salamone JC (ed) The polymeric materials encyclopedia. CRC Press, Boca Raton, pp 2102–2107
Silverstein RM, Bassler GC, Morrill TC (1991) Spectrometric identification of organic compounds, 5th edn. Wiley, New York
Socrates G (1994) Infrared characteristic group frequencies. Wiley, New York
Ikeda R, Uyama H, Kobayashi S (1996) Novel synthetic pathway to a poly(phenylene oxide). laccase-catalyzed oxidative polymerization of syringic acid. Macromolecules 29:3053–3054
Uyama H, Kurioka S, Sugihara J, Kobayashi S (1996) Enzymatic synthesis and thermal properties of a new class of polyphenol. Bull Chem Soc Jpn 69:189–193
Kobayashi S, Shoda S, Uyama H (1997) Enzymatic catalysis. In: Kobayashi S (ed) Catalysis in precision polymerization, chap 8. Wiley, Chichester
Tonami H, Uyama H, Kobayashi S (1999) Chemoenzymatic synthesis of a poly(hydroquinone). Macromol Chem Phys 200:1998–2002
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Cui, Y., Han, X., Ding, Y. et al. Enzymatic synthesis of polyphenols with longer conjugation lengths. Polym. Bull. 64, 647–656 (2010). https://doi.org/10.1007/s00289-009-0163-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-009-0163-7