THE SYNTHESIS OF SPHERICAL SHAPE AMINO FUNCTIONALIZED PEI-TGIC COVALENT ORGANIC FRAMEWORKS: SYNTHESIS, CHARACTERIZATION, AND METHYL ORANGE ABSORPTION

Abstract

In here, the synthesis of covalent organic framework (COF) from the reaction of polyethyleneimine (PEI) and triglycidyl isocyanurate (TGIC) in dimethylformamide at 90 oC were carried out. The surface are, pore volume and pore size values of PEI-TGIC COFs observed as 23.4 m2/g, 0.143 cm3/g, and 22.5 nm, respectively. Moreover, the surface charge of PEI-TGIC COFs increased to +46.1±2.6 mV from +18.3±1.7 mV, after protonation of amine groups of PEI-TGIC COFs. Moreover, the potential usage of PEI-TGIC based COFs in absorption methyl orange (MO) dye from aqueous media was testing. It was observed that, the PEI-TGIC COF absorbed 156.6±4.9 mg/g MO, and the protonated PEI-TGIC (p-PEI-TGIC) COFs absorbed 202.4±5.3 mg/g MO from aqueous media in 30 min. The MO absorption by PEI-TGIC COF fitted with pseudo-first-order kinetic model, whereas MO absorption by p-PEI-TGIC COF fitted with pseudo-second-order kinetic model.

Keywords

• Covalent organic framework
• COF
• PEI-TGIC
• methyl orange absorption

References

1. [1] THOMAS, A. 2010, Functional materials: from hard to soft porous frameworks. Angew. Chem. Int. Ed., 49, 8328.
2. [2] ZAYED, J.M., NOUVEL, N., RAUWALD, U., SCHERMAN, O.A. 2010, Chemical complexity—supramolecular self-assembly of synthetic and biological building blocks in water. Chem. Soc. Rev., 39, 2806.
3. [3] DING, S.Y. WANG, W. 2013, Covalent organic frameworks (COFs): from design to applications. Chem. Soc. Rev., 42, 548
4. [4] FUJITA, M. YAZAKI, J. OGURA, K. 1990, Preparation of a macrocyclicpolynuclear complex, [(en)Pd(4,4'-bpy)]4(NO3)8 (en = ethylenediamine, bpy = bipyridine), which recognizes an organic molecule in aqueous media. J. Am. Chem. Soc., 112, 5645.
5. [5] Special issues for metal organic frameworks: Chem. Soc. Rev., 2009, 38, 1201; Chem. Rev., 2012, 112, 673.
6. [6] GREIM, J., SCHWETZ, K., BORON CARBIDE, A. 2006, Boron Nitride, and Metal Borides; Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA,
7. [7] COˆTE´, A.P. BENIN, A. I. OCKWIG, N. W.’KEEFFE, M. O MATZGER, A. J. YAGHI, O. M. 2005, Porous, crystalline, covalent organic frameworks. Science, 310, 1166.
8. [8] MCCRUM, N.G., BUCKLEY, C.P., BUCKNALL, C.B. 1997, Principles of polymer engineering, Oxford University Press, New York,

9. [9] DAVIS, M.E. 2002, Ordered porous materials for emerging applications. Nature, , 417, 813.
10. [10] BLAKE, A.J., CHAMPNESS, N.R., CREW, M., PARSONS, S. 1999,Sawhorse connections in a Ag(I)-nitrite coordination network: {[Ag(pyrazine)]NO2}∞. New J. Chem., 23, 13.
11. [11] DAWSON, R., COOPER, A.I., ADAMS D.J. 2011, Nanoporous organic polymer networks. Prog.Polym.Sci., 37, 530.
12. [12] TONG, M.L. YU, X.L., CHEN, X.M., YU X.L., MAK, T.C.W. 1998, A novel two-dimensional rectangular network. Synthesis and structure of {[Cu(4,4′-bpy)(pyz)(H2O)2][PF6]2}n (4,4′-bpy = 4,4′-bipyridine, pyz = pyrazine). J. Chem. Soc. Dalton Trans., 5.
13. [13] COOPER, A.I. 2009. Conjugated Microporous Polymers. Adv. Mater., 21, 1291.
14. [14] TAN, L., TAN, B. 2017, Hypercrosslinked porous polymer materials: design, synthesis, and applications. Chem. Soc. Rev., 46, 3322.
15. [15] ROBESON, L.M., DOSE, M.E., FREEMAN, B.D., PAUL, D.R., 2017, Analysis of the transport properties of thermally rearranged (TR) polymers and polymers of intrinsic microporosity (PIM) relative to upper bound performance. J. Memb. Sci.,, 525, 18.
16. [16] SPRICK, R.S., BONILLO, B., SACHS, M., CLOWES, R.,. DURRANT, J.R, ADAMS, D.J., COOPER, A.I. 2012, Special issues for metal organic frameworks: Chem. Soc. Rev., 2009, 38, 1201; Chem. Rev., 112, 673. Extended conjugated microporous polymers for photocatalytic hydrogen evolution from water.Chem. Comm., 2016, 52, 10008.
17. [17] SAHINER, N., DEMIRCI, S. 2016, Poly ionic liquid cryogel of polyethyleneimine: Synthesis, characterization, and testing in absorption studies. J. Appl. Polym. Sci., 133, 43478.
18. [18] BEN, T., REN, H., MA, S., CAO, D., LAN, J., JING, X., WANG, W., XU, J., DENG, F., SIMMONS, J.M., QIU, S., ZHU, G. 2009, argeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area. Angew.Chem., Int. Ed., 48, 9457.
19. [19] MALY, K.E. 2009, Assembly of nanoporous organic materials from molecular building blocks. J. Mater. Chem., 19, 1781.
20. [20] SAHINER, N., DEMIRCI, S., SEL, K. 2016, Covalent organic framework based on melamine and dibromoalkanes for versatile use. J. Porous Mater., 23, 105.
21. [21] SAHINER, N., DEMIRCI, S. 2019, The use of covalent organic frameworks as template for conductive polymer synthesis and their sensor applications. J. Porous Mater., 26, 481.
22. [22] LI, Z., ZHI, Y., FENG, Z., DING, X., ZOU, Y., LIU, X., MU, AN AZINE Y., 2015, Linked Covalent Organic Framework: Synthesis, Characterization and Efficient Gas Storage. Chem. Eur. J.,, 21, 12079.
23. [23] BISWAL, B.P., CHAUDHARI, H.D., BANERJEE, R., KHARUL, U.K. 2016, Chemically stable covalent organic framework (COF), polybenzimidazole hybrid membranes: enhanced gas separation through pore modulation. Chem. Eur. J., 22, 4695.
24. [24] RAZAVI S.H., AHMADI R., ZAHEDI A., 2019, Modeling, simulation and dynamic control of solar assisted ground source heat pump to provide heating load and DHW. Appl. Therm. Eng., , 128, 127.
25. [25] MANDAL, A.K., MAHMOD, J., BAEK, J. B, 2017,Two, Dimensional Covalent Organic Frameworks for Optoelectronics and Energy Storage. Chem Nano Mat., 3, 373.
26. [26] BOBBITT, N.S. MENDONCA M.L., HOWARTH A.J., ISLAMOGLU T., HUPP J.T., FARHA O.K., SNURR R.Q. 2017, Metal-organic frameworks for the removal of toxic industrial chemicals and chemical warfare agents. Chem. Soc. Rev., 46, 3357.
27. [27] BAI, L. PHUA S.Z.F., LIM W.Q., JANA A., LUO Z., THAM H.P., ZHO L., GAO Q., ZHAO Y. 2016, Nanoscale covalent organic frameworks as smart carriers for drug delivery. Chem. Comm., 52, 4128.
28. [28]. CLARKE, E.A.R. 1980, vol. 3, part A. New York: Springer-Verlag, p. 181.
29. [29] ZOLLINGER, H. 1987, Azo dyes and pigments. Colour chemistry-synthesis, properties and applications of organic dyes and pigments. New York: VCH,. p. 92.
30. [30] MISHRA, G., TRIPATHY, M., 1993, A critical review or the treatments for decolourisation of textle effluent. Colourage, 40, 35.
31. [31] BANAT, I.M., NIGAM, P., SINGH, D., MARCHANT, R. 1996, Microbial decolourization of textile-dye-containing effluents: A review. Bioresour. Technol., 58, 217.
32. [32] FU, Y., VIRARAGHAVAN, T. 2001, Fungal decolorization of dye wastewaters: a review. Bioresour. Technol., 79, 251.
33. [33] ROBINSON, T., MCMULLAN, G., MARCHANT, R., NIGAM, P. 2001, Remediation of dyes in textile effluent: a critical review on current treatment technologies with a proposed alternative. Bioresour.Technol., 77, 247.
34. [34] KARCHER, S., KORNMULLER, A., JEKEL, M. 1999. Removal of Reactive Dyes by Sorption/Complexation with Cucurbituril, Water Sci. Technol., 40, 425.
35. [35] SUMATHI, S., MANJU, B.S, 2000, Uptake of reactive textile dyes by Aspergillus foetidus. Enzyme Microbial.Technol., 27, 347.
36. [36] MITTAL A.K., GUPTA S.K. 1996, Biosorption of cationic dyes by dead macro fungus fomitopsiscarnea: batch studies.Water Sci. Technol., 34, 157.
37. [37] FU, Y., VIRARAGHAVAN, T. 2002, Removal of Congo Red from an aqueous solution by fungus Aspergillusniger. Adv. Environ. Res., 7, 239.
38. [38] FRANCOS, X.F., 2014, Theoretical modeling of the effect of proton donors and regeneration reactions in the network build-up of epoxy thermosets using tertiary amines as initiators. Eur. Polym. J., 55, 35.
39. [39] ZVETKOV, V.L., KRASTEV, R.K, SAMICHKOV, V.I. 2008, Rate equations in the study of the DSC kinetics of epoxy-amine reactions in an excess of epoxy. Thermochim. Acta, 478, 17.
40. [40] MIJOVIC, J., ANDJELIC S., WINNIE YEE C.F., BELLUCCI F, NICOLAIS L., 1995, A Study of Reaction Kinetics by Near-Infrared Spectroscopy. 2. Comparison with Dielectric Spectroscopy of Model and Multifunctional Epoxy/Amine Systems.Macromolecules, 28, 2797.
41. [41] MIJOVIC, J., FISHBAIN A., WIJAYA J. 1992, Mechanistic modeling of epoxy-amine kinetics. 1. Model compound study. Macromolecules, 25, 979.
42. [42] MIJOVIC, J., FISHBAIN, A., WIJAYA, J. 1992, Mechanistic modeling of epoxy-amine kinetics. 2. Comparison of kinetics in thermal and microwave fields. Macromolecules, 25, 986.
43. [43] ZHANG, Z., ZHANG, Y.J., LU, L.H., SI, Y.J., ZHANG, S., CHEN, Y., DAI, K., DUAN P., DUAN, L.M., LIU, J.H. 2017, Graphitic carbon nitride nanosheet for photocatalytic hydrogen production: The impact of morphology and element composition. Appl. Surf.Sci., 391, 369.
44. [44] DONG, F., LI, Y.H., HO, W.K., ZHANG, H.D., FU, M., WU, Z.B. 2014, Synthesis of mesoporous polymeric carbon nitride exhibiting enhanced and durable visible light photocatalytic performance. Chin. Sci. Bull., 59, 688.
45. [45] KIM, T.H., PARK, C., YANG, J., KIM, S. 2004, Comparison of disperse and reactive dye removals by chemical coagulation and Fenton oxidation. J. Hazard. Mater., 112, 95.
46. [46] AJMAL, M., DEMIRCI, S., SIDDIQ, M., AKTAS, N., SAHINER, N. 2016, Simultaneous catalytic degradation/reduction of multiple organic compounds by modifiable p(methacrylic acid-co-acrylonitrile)–M (M: Cu, Co) microgel catalyst composites. New J. Chem., 40, 1485.
47. [47] PAULINO A.T., GUILHERME M.R., REIS A.V., CAMPESE G.M., MUNIZ E.C, NOZAKI, J. 2006, Removal of methylene blue dye from an aqueous media using superabsorbent hydrogel supported on modified polysaccharide. J. Coll. Inter. Sci., 301, 55.
48. [48] HABEEB, O.A., KANTHASAMY, R., ALI, G.A.M., YUNUS R.B.M.,. OLALERE O.A. 2017, Kinetic, isotherm and equilibrium study of adsorption of hydrogen sulfide from wastewaters using modified eggshells. IIUM Eng. J. 18, 1.