Citation:
Hong-Yu Guo, Fa-Fu Yang, Zi-Yu Jiao, Jian-Rong Lin. Click synthesis and dye extraction properties of novel thiacalix[4]arene derivatives with triazolyl and hydrogen bonding groups[J]. Chinese Chemical Letters,
;2013, 24(6): 450-452.
-
Using a click reaction between alkynylthiacalix[4]arene and ethyl 2-azidoacetate followed by an ammonolysis with ethanolamine, leucinol and hydrazine hydrate, respectively, three novel thiacalix[4]arene derivatives 4, 5 and 6 with triazolyl and hydrogen bonding groups (NH and OH) were synthesized in high yields. They exhibited excellent extraction capability for six anionic and cationic dyes. The flexible cavity, π-triazole rings and hydrogen bonding groups all play crucial roles in dye complexation.
-
Keywords:
- Thiacalix[4]arene,
- Synthesis,
- Click chemistry,
- Dye extraction
-
-
-
[1]
[1] Y. Wong, J. Yu, Laccase-catalyzed decolorization of synthetic dyes, Water Res. 33 (1999) 3512-3519.
-
[2]
[2] G. Crini, Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment, Prog. Polym. Sci. 30 (2005) 38-46.
-
[3]
[3] I.T. Peternel, N. Koprivanac, A.M.L. Bozic, et al., Comparative study of UV/TiO2, UV/ ZnO and photo-Fenton processes for the organic reactive dye degradation in aqueous solution, J. Hazard. Mater. 148 (2007) 477-484.
-
[4]
[4] G. Crini, P.M. Badot, 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 (2008) 399-447.
-
[5]
[5] M.K. Purkait, S. DasGupta, S. De, Resistance in series model for micellar enhanced ultrafiltration of eosin dye, J. Colloid Interface Sci. 270 (2004) 496-506.
-
[6]
[6] S. Chakraborty, M.K. Purkait, S. DasGupta, et al., Nanofiltration of textile plant effluent for color removal and reduction in COD, Sep. Purif. Technol. 31 (2003) 141-151.
-
[7]
[7] D. Ghosh, K.G. Bhattacharyya, Adsorption of metheylene blue on kaolinite, Appl. Clay Sci. 20 (2002) 295-300.
-
[8]
[8] Y. Al-Degs, M.A.M. Khraisheh, S.J. Allen, et al., Sorption behavior of cationic and anionic dyes from aqueous solution on different types of activated carbons, Sep. Sci. Technol. 36 (2001) 91-102.
-
[9]
[9] P.R. Jana, S. De, J.K. Basu, A generalized shrinking core model applied to batch adsorption, Chem. Eng. J. 95 (2003) 143-154.
-
[10]
[10] F.C. Wu, R.L. Tseng, R.S. Juang, Comparative adsorption of metal and dye on flakeand bead-types of chitosan prepared from fishery wastes, J. Hazard. Mater. 73 (2000) 63-75.
-
[11]
[11] E. Akceylan, M. Bahadir, M. Yilmaz, Removal efficiency of a calix[4]arene-based polymer for water-soluble carcinogenic direct azo dyes and aromatic amines, J. Hazard. Mater. 162 (2009) 960-966.
-
[12]
[12] E.O. Yilmaz, A. Sirit, M. Yilmaz, A calix[4]arene oligomer and two betacyclodextrin polymers: synthesis and sorption studies of azo dyes, J. Macromol. Sci. A: Pure Appl. Chem. 44 (2007) 167-174.
-
[13]
[13] A. Yilmaz, E. Yilmaz, M. Yilmaz, et al., Removal of azo dyes from aqueous solutions using calix[4]arene and cyclodextrin, Dyes Pigm. 74 (2007) 54-60.
-
[14]
[14] M.A. Kamboh, I.B. Solangi, S.T.H. Sherazi, et al., A highly efficient calix[4]arene based resin for the removal of azo dyes, Desalination 268 (2011) 83-89.
-
[15]
[15] M.A. Kamboh, I.B. Solangi, S. Memon, Synthesis and application of p-tert-butylcalix[8]arene immobilized material for the removal of azo dyes, J. Hazard. Mater. 186 (2011) 651-656.
-
[16]
[16] M. Chen, T. Shang, W. Fang, G. Diao, Study on adsorption and desorption properties of the starch grafted p-tert-butyl-calix[n]arene for butyl Rhodamine B solution, J. Hazard. Mater. 185 (2011) 914-920.
-
[17]
[17] E.H. Ryu, Y. Zhao, Efficient synthesis of water-soluble calixarenes using click chemistry, Org. Lett. 7 (2005) 1035-1037.
-
[18]
[18] S.P. Bew, R.A. Brimage, N.L. Hermite, et al., Upper rim appended hybrid calixarenes via click chemistry, Org. Lett. 9 (2007) 3713-3717.
-
[19]
[19] O. Gungor, A. Yilmaz, S. Memon, et al., Evaluation of the performance of calix[8]-arene derivatives as liquid phase extraction material for the removal of azo dyes, J. Hazard. Mater. 158 (2008) 202-210.
-
[1]
-
-
-
[1]
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
-
[2]
Huiju Cao , Lei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
-
[3]
Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO2 and selectivity over N2 and CH4. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
-
[4]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[5]
Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
-
[6]
Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
-
[7]
Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
-
[8]
Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
-
[9]
Juanjuan Wang , Fang Wang , Bin Qin , Yue Wu , Huan Yang , Xiaolong Li , Lanfang Wang , Xiufang Qin , Xiaohong Xu . Controlled synthesis and excellent magnetism of ferrimagnetic NiFe2Se4 nanostructures. Chinese Chemical Letters, 2024, 35(11): 109449-. doi: 10.1016/j.cclet.2023.109449
-
[10]
Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
-
[11]
Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
-
[12]
Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C3N4-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
-
[13]
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
-
[14]
Jindong Hao , Yufen Lv , Shuyue Tian , Chao Ma , Wenxiu Cui , Huilan Yue , Wei Wei , Dong Yi . Additive-free synthesis of β-keto phosphorodithioates via geminal hydro-phosphorodithiolation of sulfoxonium ylides with P4S10 and alcohols. Chinese Chemical Letters, 2024, 35(9): 109513-. doi: 10.1016/j.cclet.2024.109513
-
[15]
Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na3V2(PO4)3 cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
-
[16]
Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
-
[17]
Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
-
[18]
Hang Wang , Qi Wang , Chuan-De Wu . Continuous synthesis of ammonia. Chinese Journal of Structural Chemistry, 2025, 44(3): 100437-100437. doi: 10.1016/j.cjsc.2024.100437
-
[19]
Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe2Sn4Bi8]3– and [Cr2Sb12]3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
-
[20]
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(700)
- HTML views(11)