Multi-Stimuli-Responsive Organogel Based on Bisthiourea Compounds for The Removal of Selected Organic Dyes
The self-assembly of a series of bisthiourea containing amino acid side chains has been studied in a large range of organic solvents. Self-assembly is driven mainly by hydrogen bonding groups of thiourea and amino acids moieties. Of all the synthesized compounds, only bisthiourea with alanine side chains, 3.5 formed thermoreversible gel in 50:3 dichloromethane:water mixture at minimum gel concentration of 0.5%. SEM micrographs of the gel showed the formation of entangled cross-linked fibres. The addition of anions such as Cl¯, F¯ and AcO¯ disrupted the gel network of 3.5 thus inducing the gel-sol transition. To investigate the ability of the bisthiourea to form metallogel, metal ions such as Co2+, Cu2+, Ni2+ and Pb2+ were introduced, however, none of them induce the formation of metallogel. In particular, the gels show good performance in the absorption of bromocresol green and Eriochrome black-T at 75% and 61% efficiency, respectively within 24 hours. The good dye absorption properties of gel 3.5 render the potential of bisthiourea gels as new dye absorption materials, which show significant benefit for water pollution treatment.
Bachl, J., Sampedro, D., Mayr, J. & Diaz Diaz, D. (2017). Ultrasonication-enhanced gelation properties of a versatile amphiphilic formamidine-based gelator exhibiting both organogelation and hydrogelation abilities. Physical Chemistry Chemical Physics, 19(34): 22981–22994.
Baddi, S., Madugula, S.S., Sarma, D.S., Soujanya, Y. & Palanisamy, A. (2015). Combined experimental and computational study of the gelation of cyclohexane-based bis(acyl-semicarbazides) and the multi-stimuli-responsive properties of their gels. Langmuir, 32(3): 889–899.
Bai, B., Mao, X., Wei, J., Wei, Z., Wang, H. & Li, M. (2015). Selective anion-responsive organogel based on a gelator containing hydrazide and azobenzene units. Sensors and Actuators B: Chemical, 211: 268–274.
Blažek Bregović, V., Basarić, N. & Mlinarić-Majerski, K. (2015). Anion binding with urea and thiourea derivatives. Coordination Chemistry Reviews, 295: 80–124.
Cao, X., Zhao, N., Lv, H., Gao, A., Shi, A., & Wu, Y. (2018). 4-Nitrobenzene thiourea self-assembly system and its transformation upon addition of Hg2+ ion: Applications as sensor to fluoride ion. Sensors and Actuators, B: Chemical, 266: 637–644.
Cheng, N., Kang, Q., Xiao, J., Du, N. & Yu, L. (2018). Supramolecular gels: using an amide-functionalized imidazolium-based surfactant. Journal of Colloid and Interface Science, 511: 215–221.
Chetia, M., Debnath, S., Chowdhury, S. & Chatterjee, S. (2020). Self-assembly and multifunctionality of peptide organogels: Oil spill recovery, dye absorption and synthesis of conducting biomaterials. RSC Advances, 10(9): 5220–5233.
Christoff-tempesta, T., Lew, A. & Ortony, J. (2018). Beyond Covalent Crosslinks: Applications of Supramolecular Gels. Gels, 4(2): 1–40.
Dastidar, P., Ganguly, S. & Sarkar, K. (2016). Metallogels from Coordination Complexes, Organometallic, and Coordination Polymers. Chemistry - An Asian Journal, 11(18): 2484–2498.
De, A. & Mondal, R. (2018). Toxic Metal Sequestration exploiting an unprecedented low-molecular-weight hydrogel-to metallogel transformation. ACS Omega, 3(6): 6022-6030.
Fakhar, I.M., Yamin, B. & Hasbullah, S.A. (2016). Synthesis and characterization of bis-thiourea having amino acid derivatives. American Institute of Physics, 1784(1): 1–7.
Ha, S., Lee, J., Kim, K.S., Choi, E. J., Nhem, P. & Song, C. (2019). Anion-responsive thiourea-based gel actuator. Chemistry of Materials, 31(15): 5735–5741.
Han, L., He, Y., An, R., Wang, X., Zhang, Y., Shi, L. & Ran, R. (2019). Mussel-inspired, robust and self-healing nanocomposite hydrogels: Effective reusable absorbents for removal both anionic and cationic dyes. Colloids and Surfaces A, 569: 18–27.
Hooper, A.E., Kennedy, S.R., Jones, C.D. & Steed, J.W. (2016). Gelation by supramolecular dimerization of mono(urea)s. Chemical Communications, 52(1): 198–201.
Khan, I., Ur Rahman, N., Ali, A. & Saeed, K. (2019). Adsorption of cobalt onto activated charcoal and its utilization for decolorization of bromocresol green dye. Bulgarian Chemical Communications, 51(4): 488–493.
Kyzas, G. Z., Siafaka, P. I. Pavlidou, E. G., Chrissafis, K. J., & Bikiaris, D. N. (2015). Synthesis and adsorption application of succinyl-grafted chitosan for the simultaneous removal of zinc and cationic dye from binary hazardous mixtures. Chemical Engineering Journal, 259: 438–448.
Li, L., Zhou, N., Kong, H. & He, X. (2019). Controlling the supramolecular polymerization and metallogel formation of Pt(II) complexes via delicate tuning of non-covalent interactions. Polymer Chemistry, 10(40): 5465–5472.
Liu, J., Xu, F., Sun, Z., Pan, Y., Tian, J., Lin, H.C. & Li, X. (2016). A supramolecular gel based on a glycosylated amino acid derivative with the properties of gel to crystal transition. Soft Matter, 12(1): 141–148.
Liu, Y., Wang, Y., Jin, L., Chen, T. & Yin, B. (2016). MPTTF-containing tripeptide- based organo gels: receptor for 2,4,6-trinitrophenol and multiple stimuli-responsive properties. Soft Matter, 12(3): 934–945.
Mondal, S. & Dastidar, P. (2018). Mixed ligand coordination polymers for metallogelation and iodine adsorption. Crystal Growth and Design, 19(1): 470-478.
Okesola, B.O. & Smith, D.K. (2016). Applying low-molecular weight supramolecular gelators in an environmental setting-self-assembled gels as smart materials for pollutant removal. Chemical Society Reviews, 45(15): 4226–4251.
Panja, A. & Ghosh, K. (2018). Diaminomalenonitrile -decorated cholesterol -based supra molecular gelator: aggregation, multiple analyte (hydrazine, Hg2+ and Cu2+) detection and dye adsorption. New Journal of Chemistry, 42(16): 13718–13725.
Panja, A., Ghosh, S. & Ghosh, K. (2019). A sulfonyl hydrazine cholesterol conjugate: gelation, anion interaction and its application in dye absorption. New Journal of Chemistry, 42: 10270–10277.
Sengupta, S., Goswami, A. & Mondal, R. (2014). Silver-promoted gelation studies of an unorthodox chelating tripodal pyridine-pyrazole-based ligand: Templated growth of catalytic silver nanoparticles, gas and dye adsorption. New Journal of Chemistry, 38(6): 2470–2479.
Staicu, T., Iliş, M., Cîrcu, V. & Micutz, M. (2018). Influence of hydrocarbon moieties of partially fluorinated N-benzoyl thiourea compounds on their gelation properties. A detailed rheological study of complex viscoelastic behavior of decanol/N-benzoyl thiourea mixtures. Journal of Molecular Liquids, 255: 297–312.
Tatikonda, R., Bhowmik, S., Rissanen, K., Haukka, M. & Cametti, M. (2016). Metallogel formation in aqueous DMSO by perfluoroalkyl decorated terpyridine ligands. Dalton Transactions, 45(32): 12756–12762.
Wezenberg, S.J., Croisetu, C.M., Stuart, M.C.A. & Feringa, B.L. (2016). Reversible gel-sol photoswitching with an overcrowded alkene-based bis-urea supergelator. Chemical Science, 7(7): 4341–4346.
Yang, Z., Wu, G., Gan, C., Cai, G., Zhang, J. & Ji, H. (2021). Effective adsorption of arsenate, dyes and eugenol from aqueous solutions by cationic supramolecular gel materials. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 616: 126238.
Copyright (c) 2022 Borneo Journal of Resource Science and Technology
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Copyright Transfer Statement for Journal
1) In signing this statement, the author(s) grant UNIMAS Publisher an exclusive license to publish their original research papers. The author(s) also grant UNIMAS Publisher permission to reproduce, recreate, translate, extract or summarize, and to distribute and display in any forms, formats, and media. The author(s) can reuse their papers in their future printed work without first requiring permission from UNIMAS Publisher, provided that the author(s) acknowledge and reference publication in the Journal.
2) For open access articles, the author(s) agree that their articles published under UNIMAS Publisher are distributed under the terms of the CC-BY-NC-SA (Creative Commons Attribution-Non Commercial-Share Alike 4.0 International License) which permits unrestricted use, distribution, and reproduction in any medium, for non-commercial purposes, provided the original work of the author(s) is properly cited.
3) For subscription articles, the author(s) agree that UNIMAS Publisher holds copyright, or an exclusive license to publish. Readers or users may view, download, print, and copy the content, for academic purposes, subject to the following conditions of use: (a) any reuse of materials is subject to permission from UNIMAS Publisher; (b) archived materials may only be used for academic research; (c) archived materials may not be used for commercial purposes, which include but not limited to monetary compensation by means of sale, resale, license, transfer of copyright, loan, etc.; and (d) archived materials may not be re-published in any part, either in print or online.
4) The author(s) is/are responsible to ensure his or her or their submitted work is original and does not infringe any existing copyright, trademark, patent, statutory right, or propriety right of others. Corresponding author(s) has (have) obtained permission from all co-authors prior to submission to the journal. Upon submission of the manuscript, the author(s) agree that no similar work has been or will be submitted or published elsewhere in any language. If submitted manuscript includes materials from others, the authors have obtained the permission from the copyright owners.
5) In signing this statement, the author(s) declare(s) that the researches in which they have conducted are in compliance with the current laws of the respective country and UNIMAS Journal Publication Ethics Policy. Any experimentation or research involving human or the use of animal samples must obtain approval from Human or Animal Ethics Committee in their respective institutions. The author(s) agree and understand that UNIMAS Publisher is not responsible for any compensational claims or failure caused by the author(s) in fulfilling the above-mentioned requirements. The author(s) must accept the responsibility for releasing their materials upon request by Chief Editor or UNIMAS Publisher.
6) The author(s) should have participated sufficiently in the work and ensured the appropriateness of the content of the article. The author(s) should also agree that he or she has no commercial attachments (e.g. patent or license arrangement, equity interest, consultancies, etc.) that might pose any conflict of interest with the submitted manuscript. The author(s) also agree to make any relevant materials and data available upon request by the editor or UNIMAS Publisher.