, Volume 20, Issue 2, pp 895–906 | Cite as

Triphenylene-modified chitosan: novel high efficient sorbent for cationic and anionic dyes

  • Fafu Yang
  • Xiaoyan Bai
  • Bingting Xu
  • Hongyu Guo
Original Paper


The first example of triphenylene-modified chitosan 4 was prepared by reacting chitosan with triphenylene aldehyde derivative 3. Its structure and morphology was characterized by elemental analysis, 1H NMR, FTIR, XRD, SEM and AFM image. The triphenylene units in Tp-chitosan 4 appended on the skeleton of chitosan and possessed orderly layered structure. Adsorption experiments of Tp-chitosan 4 indicated that it possessed excellent adsorption capacities for both cationic and anionic dyes [Orange G sodium salt, Brilliant ponceau 5R, Victoria blue B (VB), Crystal violet (CV), Neutral red (NR) and Methylene blue]. The highest adsorption capacities for CV, VB and NR were 5.612, 5.353 and 5.375 mmol/g, respectively. Adsorption kinetics and isotherms analysis showed that the adsorption processes obeyed pseudo second-order model and the Langmuir isotherm equation. The adsorption processes were exothermic and spontaneous. The best pH values for adsorption were pH = 6–8.


Chitosan Triphenylene Adsorption Dye 



Financial support from the National Natural Science Foundation of China (No: 20402002), Fujian Natural Science Foundation of China (No. 2011J01031), Project of Fujian provincial department of education(JA11044) and Program for Excellent young researchers in University of Fujian Province (JA10056) were greatly acknowledged.


  1. Al-Degs Y, Khraisheh MAM, Allen SJ, Ahmad MNA (2001) Sorption behavior of cationic and anionic dyes from aqueous solution on different types of activated carbons. Sep Sci Technol 36:91–102CrossRefGoogle Scholar
  2. Bengisu M, Yilmaz E (2002) Oxidation and pyrolysis of chitosan as a route for carbon fiber derivation. Carbohydr Polym 50:165–175CrossRefGoogle Scholar
  3. Cestari AR, Vieira EFS, Mota JA (2008) The removal of an anionic red dye from aqueous solutions using chitosan beads-The role of experimental factors on adsorption using a full factorial design. J Hazard Mater 160:337–343CrossRefGoogle Scholar
  4. Chakraborty S, Purkait MK, DasGupta S, De S, Basu JK (2003) Nanofiltration of textile plant effluent for color removal and reduction in COD. Sep Purif Technol 31:141–151CrossRefGoogle Scholar
  5. Chao AC, Shyu SS, Lin YC, Mi FL (2004) Enzymatic grafting of carboxyl groups on to chitosan—to confer on chitosan the property of a cationic dye adsorbent. Bioresour Technol 91:157–162CrossRefGoogle Scholar
  6. Chatterjee S, Chatterjee S, Chatterjee BP, Das AR (2005a) Adsorption of a model anionic dye, ecosin Y, from aqueous solution by chitosan hydrobeads. J Colloid Interface Sci 288:30–35CrossRefGoogle Scholar
  7. Chatterjee S, Chatterjee S, Chatterjee BP, Das AR, Guha AK (2005b) Adsorption of a model anionic dye, eosin Y, from aqueous solution by chitosan hydrobeads. J Colloid Interface Sci 288:30–35CrossRefGoogle Scholar
  8. Chen AH, Chen SM (2009) Biosorption of azo dyes from aqueous solution by glutaraldehyde- crosslinked chitosans. J Hazard Mater 172:1111–1121CrossRefGoogle Scholar
  9. Chen CY, Chang JC, Chen AH (2011) Competitive biosorption of azo dyes from aqueous solution on the template crosslinked-chitosan nanoparticles. J Hazard Mater 185:430–441CrossRefGoogle Scholar
  10. Chiou MS, Chuang GS (2006) Competitive adsorption of dye metanil yellow and RB15 in acid solution on chemically cross-linked chitosan beads. Chemosphere 62:731–740CrossRefGoogle Scholar
  11. Chiou MS, Li HY (2002) Equilibrium and kinetic modeling of adsorption of reactive dye on crosslinked chitosan beads. J Hazard Mater 93:233–248CrossRefGoogle Scholar
  12. Chiou MS, Ho PY, Li HY (2004) Adsorption of anionic dyes in acid solutions using chemically cross-linked chitosan beads. Dyes Pigments 60:69–84CrossRefGoogle Scholar
  13. Crini G (2005) Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment. Prog Polym Sci 30:38–70CrossRefGoogle Scholar
  14. Crini G, Badot PM (2008) Application of chitosan, a natural aminopolysaccharide, for dye removal from aqueous solutions by adsorption processes using bath studies: a review of recent literature. Prog Polym Sci 33:399–447CrossRefGoogle Scholar
  15. Du WL, Xu ZR, Han XY, Xu YL, Miao ZG (2008) Preparation, characterization and adsorption properties of chitosan nanoparticles for eosin Y as a model anionic dye. J Hazard Mater 153:152–156CrossRefGoogle Scholar
  16. Duan W, Shen C, Fang H, Li GH (2009) Synthesis of dehydroabietic acid-modified chitosan and its drug release behavior. Carbohydr Res 344:9–13CrossRefGoogle Scholar
  17. Elwakeel KZ (2009) Removal of reactive black 5 from aqueous solutions using magnetic chitosan resins. J Hazard Mater 167:383–392CrossRefGoogle Scholar
  18. Giles CH, Smith D, Huitson A (1974) A general treatment and classification of the solute adsorption isothermI. I. Theoretical. J Colloid Interface Sci 47:755–765CrossRefGoogle Scholar
  19. Gu YX, Song P, Li T, Sui WP (2011) Synthesis and characterization of carboxymethyl- polyaminate chitosan and its adsorption behavior toward a reactive dye. Carbohydr Res 346:769–774CrossRefGoogle Scholar
  20. Guibal E (2004) Interactions of metal ions with chitosan-based sorbents: a review. Sep Purif Technol 38:43–74CrossRefGoogle Scholar
  21. Hu ZG, Zhang J, Chan WL, Szeto YS (2006) The sorption of acid dye onto chitosan nanoparticles. Polymer 47:5838–5842CrossRefGoogle Scholar
  22. Huang XY, Bin J, Bu HT, Jiang GB, Zeng MH (2011) Removal of anionic dye eosin Y from aqueous solution using ethylenediamine modified chitosan. Carbohydr Polym 84:1350–1356CrossRefGoogle Scholar
  23. Jana PR, De S, Basu JK (2003) A generalized shrinking core model applied to batch adsorption. Chem Eng J 95:143–154CrossRefGoogle Scholar
  24. Kaczmarek H, Zawadzki J (2010) Chitosan pyrolysis and adsorption properties of chitosan and its carbonizate. Carbohydr Res 345:941–947CrossRefGoogle Scholar
  25. Kitkulnumchai Y, Ajavakom A, Sukwattanasinitt M (2008) Treatment of oxidized cellulose fabric with chitosan and its surface activity towards anionic reactive dyes. Cellulose 15:599–608CrossRefGoogle Scholar
  26. Kumar S, Pal SK (2005) Ionic discotic liquid crystals: synthesis and characterization of pyridinium bromides containing a triphenylene core. Tetrahedron Lett 46:4127–4130CrossRefGoogle Scholar
  27. Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403CrossRefGoogle Scholar
  28. Lin BF, Du YM, Li YM, Liang XQ, Wang XY, Deng W, Wang XH, Li L, Kennedy JF (2010) The effect of moist heat treatment on the characteristic of starch-based composite materials coating with chitosan. Carbohydr Polym 81:554–559CrossRefGoogle Scholar
  29. Monvisade P, Siriphannon P (2009) Chitosan intercalated montmorillonite: preparation, characterization and cationic dye adsorption. Appl Clay Sci 42:427–431CrossRefGoogle Scholar
  30. Paraschiv I, Giesbers M, Lagen B, Grozema F, Abellon R, Siebbeles L, Marcelis A, Zuilhof H, Sudhölter E (2006) H-bond-stabilized triphenylene-based columnar discotic liquid crystals. Chem Mater 18:968–974CrossRefGoogle Scholar
  31. Peternel IT, Koprivanac N, Bozic AML, Kusic HM (2007) Comparative study of UV/TiO2, UV/ZnO and photo-Fenton processes for the organic reactive dye degradation in aqueous solution. J Hazard Mater 148:477–484CrossRefGoogle Scholar
  32. Prasad SK, Rao DS, Chandrasekhar S, Kumar S (2003) X-RAY studies on the columnar structures of discotic liquid crystals. Mol Cryst Liq Cryst 396:121–139CrossRefGoogle Scholar
  33. Purkait MK, DasGupta S, De S (2004) Resistance in series model for micellar enhanced ultrafiltration of eosin dye. J Colloid Interface Sci 270:496–506CrossRefGoogle Scholar
  34. Sopena LAS, Ruiz M, Yatluk Y, Guibal E (2011) N-(2-(2-pyridyl)ethyl)chitosan (PEC) for Pd(II) and Pt(IV) sorption from HCl solutions. Cellulose 18:309–325CrossRefGoogle Scholar
  35. Wang ZH, Xiang B, Cheng RM, Li YJ (2010) Behaviors and mechanism of acid dyes sorption onto diethylenetriamine-modified native and enzymatic hydrolysis starch. J Hazard Mater 183:224–232CrossRefGoogle Scholar
  36. Watson MD, Fechtenkotter A, Mullen K (2001) Big is beautiful-“aromaticity” revisited from the viewpoint of macromolecular and supramolecular benzene chemistry. Chem Rev 101:1267–1300CrossRefGoogle Scholar
  37. Wong Y, Yu J (1999) Laccase-catalyzed decolorization of synthetic dyes. Water Res 33:3512–3520CrossRefGoogle Scholar
  38. Yoshida H, Okamoto A, Kataoka T (1993) Adsorption of acid dye on crosslinked chitosan fibers: equilibria. Chem Eng J 48:2267–2272CrossRefGoogle Scholar
  39. Zhang L, Gopee H, Hughes DL, Cammidge AN (2010) Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional π-overlap in the solid state. Chem Commun 46:4255–4257CrossRefGoogle Scholar
  40. Zhao B, Liu B, Png RQ, Zhang K, Lim KA, Luo J, Shao J, Ho P, Chi C, Wu J (2010) New discotic mesogens based on triphenylene-fused triazatruxenes: synthesis, physical properties, and self-assembly. Chem Mater 22:435–449CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  • Fafu Yang
    • 1
    • 2
  • Xiaoyan Bai
    • 1
  • Bingting Xu
    • 1
  • Hongyu Guo
    • 1
  1. 1.College of Chemistry and Materials ScienceFujian Normal UniversityFuzhouPeople’s Republic of China
  2. 2.Fujian Key Laboratory of Polymer MaterialsFujian Normal UniversityFuzhouPeople’s Republic of China

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