Sulfonic Acid-functionalized Spherical Covalent Organic Framework with Ultrahigh Capacity for the Removal of Cationic Dyes

doi:10.7503/cjcu20200443

Abstract

Abstract:

The development of porous covalent organic frameworks（COFs） as adsorbents for highly effective and selective removal of organic pollutants from aqueous solution is desirable but remains challenging. Herein， a β-ketoenamine-linked sulfonic acid-functionalized spherical COF， namely TFP-BDSA， was synthesized by the Schiff-base reaction of 1，3，5-triformylphloroglucinol（TFP） with 2，2′-benzidinedisulfonic acid（BDSA）. The anionic nature of the framework can rapidly adsorb the cationic dyes of MLB， CV， and RhB， while it is difficult for the adsorption of MO and FS anionic dyes， making it promising for the separation of cationic and anionic dyes based on a charge-dependent mode. The adsorption kinetics of cationic dyes on TFP-BDSA all followed the Pseudo-second-order adsorption kinetic model， and the adsorption process fitted well the the Langmuir adsorption model. The maximum adsorption capacities of TFP-BDSA for MLB， CV and RhB are 1116， 1429 and 1638 mg/g， respectively， in which those of CV and RhB rank as the highest values in comparison to the other reported COFs to date. This work may provide a useful idea for developing COFs-based adsorbents for fast adsorption and effective removal of organic pollutants from wastewater.

Key words: Covalent organic frameworks（COFs）, Dye, Adsorption, Separation (Ed.: V, K, S)

CLC Number:

O622

TrendMD:

YAN Yanhong, WU Simin, YAN Yilun, TANG Xihao, CAI Songliang, ZHENG Shengrun, ZHANG Weiguang, GU Fenglong. Sulfonic Acid-functionalized Spherical Covalent Organic Framework with Ultrahigh Capacity for the Removal of Cationic Dyes[J]. Chem. J. Chinese Universities, 2021, 42(3): 956.

Figures/Tables 9

References 33

1	Cojocaru C.， Clima L.， J. Mol. Liq.， 2019， 285， 811—821
2	Rani B.， Punniyakoti S.， Sahu N. K.， New J. Chem.， 2018， 42， 943—954
3	Kausar A.， Iqbal M.， Javed A.， Aftab K.， Nazli Z. I. H.， Bhatti H. N.， Nouren S.， J. Mol. Liq.， 2018， 256， 395—407
4	Fan H.， Mundstock A.， Feldhoff A.， Knebel A.， Gu J.， Meng H.， Caro J.， J. Am. Chem. Soc.， 2018， 140， 10094—10098
5	Chen G.， Lan H. H.， Cai S. L.， Sun B.， Li X. L.， He Z. H.， Zheng S. R.， Fan J.， Liu Y.， Zhang W. G.， ACS Appl. Mater. Interfaces， 2019， 11， 12830—12837
6	Liu L. H.， Yang C. X.， Yan X. P.， J. Chromatogr. A， 2017， 1479， 137—144
7	Zhang K.， Cai S. L.， Yan Y. L.， He Z. H.， Lin H. M.， Huang X. L.， Zheng S. R.， Fan J.， Zhang W. G.， J. Chromatogr. A， 2017， 1519， 100—109
8	Hao J.， Zhang Q.， Chen P.， Zheng X.， Wu Y.， Ma D.， Wei D.， Liu H.， Liu G.， Lv W.， Environ. Sci. Nano， 2019， 6， 3374— 3387
9	Peng Y.， Hu Z.， Gao Y.， Yuan D.， Kang Z.， Qian Y.， Yan N.， Zhao D.， ChemSusChem， 2015， 8， 3208—3212
10	Li Y.， Yang C. X.， Qian H. L.， Zhao X.， Yan X. P.， ACS Appl. Mater. Interfaces， 2019， 2， 7290—7298
11	Ning G. H.， Chen Z.， Gao Q.， Tang W.， Chen Z.， Liu C.， Tian B.， Li X.， Loh K. P.， J. Am. Chem. Soc.， 2017， 139， 8897— 8904
12	Yu S. B.， Lyu H.， Tian J.， Wang H.， Zhang D. W.， Liu Y.， Li Z. T.， Polym. Chem.， 2016， 7， 3392—3397
13	Karak S.， Dey K.， Torris A.， Halder A.， Bera S.， Kanheerampockil F.， Banerjee R.， J. Am. Chem. Soc.， 2019， 141， 7572—7581
14	Yue J. Y.， Wang L.， Ma Y.， Yang P.， Zhang Y. Q.， Jiang Y.， Tang B.， Dalton Trans.， 2019， 48， 17763—17769
15	Zhu X.， An S.， Liu Y.， Hu J.， Liu H.， Tian C.， Dai S.， Yang X.， Wang H.， Abney C. W.， Dai S.， AlChE J.， 2017， 63， 3470— 3478
16	Hou Y.， Zhang X.， Wang C.， Qi D.， Gu Y.， Wang Z.， Jiang J.， New J. Chem.， 2017， 46， 6145—6151
17	Deng Q. L.， Tian Y. Y.， Liu C.， Shi H. P.， Fang G. Z.， Wang S.， RSC Adv.， 2020， 10， 5443—5453
18	Mohammed A. K.， Usgaonkar S.， Kanheerampockil F.， Karak S.， Halder A.， Tharkar M.， Addicoat M.， Ajithkumar T. G.， Banerjee R.， J. Am. Chem. Soc.， 2020， 142， 8252—8261
19	Firoozi M.， Rafiee Z.， Dashtian K.， ACS Omega.， 2020， 5， 9420—9428
20	Shi W.， Zhou Y.， Zhang Y.， Li L.， Yang Q.， Water Sci. Technol.， 2012， 66， 2638—2646
21	Pourjavadi A.， Nazari M.， Kabiri B.， Hosseini S. H.， Bennett C.， RSC Adv.， 2016， 6， 10430—10437
22	Luo X. P.， Fu S. Y.， Du Y. M.， Guo J. Z.， Li B.， Micropor. Mesopor. Mater.， 2017， 237， 268—274
23	Peng Y.， Xu G.， Hu Z.， Cheng Y.， Chi C.， Yuan D.， Cheng H.， Zhao D.， ACS Appl. Mater. Interfaces， 2016， 8， 18505—18512
24	Zhang N.， Wang T.， Wu X.， Jiang C.， Chen F.， Bai W.， Bai R.， RSC Adv.， 2018， 8， 3803—3808
25	Materials Studio Ver5.0， Accelrys Inc.， San Diego， CA， 2009
26	Shinde D. B.， Sheng G.， Li X.， Ostwal M.， Emwas A. H.， Huang K. W.， Lai Z.， J. Am. Chem. Soc.， 2018， 140， 14342—14349
27	Chandra S.， Kundu T.， Dey K.， Addicoat M.， Heine T.， Banerjee R.， Chem. Mater.， 2016， 28， 1489—1494
28	Li G. L.， Ye J. R.， Fang Q.， Liu F.， Chem. Eng. J.， 2019， 370， 822—830
29	Fang Q.， Zhuang Z.， Gu S.， Kaspar R. B.， Zheng J.， Wang J.， Qiu S.， Yan Y.， Nat. Commun.， 2014， 5， 4503
30	Gao Y.， Deng S. Q.， Jin X.， Cai S. L.， Zheng S. R.， Zhang W. G.， Chem. Eng. J.， 2019， 357， 129—139
31	Li H.， Cao X.， Zhang C.， Yu Q.， Zhao Z.， Niu X.， Sun X.， Liu Y.， Ma L.， Li Z.， RSC Adv.， 2017， 7， 16273—16281
32	Deng S. Q.， Miao Y. L.， Tan Y. L.， Fang H. N.， Li Y. T.， Mo X. J.， Cai S. L.， Fan J.， Zhang W. G.， Zheng S. R.， Inorg. Chem.， 2019， 58， 13979—13987
33	Tian S.， Xu S.， Liu J.， He C.， Xiong Y.， Feng P.， J. Clean. Prod.， 2019， 239， 117767

Sample	q_{e, exp.}/(mg·g^-1)	q_{e, cal.}/(mg·g^-1)	k₂/(g·mg^-1·min^-1)	R²
MLB	39.93	40.10	0.1138	0.99998
CV	41.58	41.82	0.0612	0.99999
RhB	39.06	38.46	0.0100	0.99953

Sample	q_{e, exp.}/(mg·g^-1)	q_{e, cal.}/(mg·g^-1)	k₂/(g·mg^-1·min^-1)	R²
MLB	39.93	40.10	0.1138	0.99998
CV	41.58	41.82	0.0612	0.99999
RhB	39.06	38.46	0.0100	0.99953

Dye	Material	q_e/(mg·g^-1)	Ref.
MLB	TpPa?SO₃	1806.9	[17]
	TS?COF?1	1691	[15]
	TS?COF?2	377	[15]
	COF?foam	108	[13]
	COF?GO foams	194	[18]
	TFP?BDSA	1112	This work
CV	COF?TzDBd	307.7	[10]
	TFP?BDSA COF	1429	This work
RhB	CuP?DMNDA?COF	429	[16]
	TS?COF?1	625	[15]
	Ttba?TPDA?COF	833	[14]
	MOF?5/COF	16.18	[19]
	COF?GO foams	194	[18]
	TFP?BDSA COF	1638	This work

Dye	Material	q_e/(mg·g^-1)	Ref.
MLB	TpPa?SO₃	1806.9	[17]
	TS?COF?1	1691	[15]
	TS?COF?2	377	[15]
	COF?foam	108	[13]
	COF?GO foams	194	[18]
	TFP?BDSA	1112	This work
CV	COF?TzDBd	307.7	[10]
	TFP?BDSA COF	1429	This work
RhB	CuP?DMNDA?COF	429	[16]
	TS?COF?1	625	[15]
	Ttba?TPDA?COF	833	[14]
	MOF?5/COF	16.18	[19]
	COF?GO foams	194	[18]
	TFP?BDSA COF	1638	This work

[1]	JIANG Hongbin, DAI Wenchen, ZHANG Rao, XU Xiaochen, CHEN Jie, YANG Guang, YANG Fenglin. Research on Co₃O₄/UiO-66@α-Al₂O₃ Ceramic Membrane Separation and Catalytic Spraying Industry VOCs Waste Gas [J]. Chem. J. Chinese Universities, 2022, 43(6): 20220025.
[2]	HAO Honglei, MENG Fanyu, LI Ruoyu, LI Yingqiu, JIA Mingjun, ZHANG Wenxiang, YUAN Xiaoling. Biomass Derived Nitrogen Doped Porous Carbon Materials as Adsorbents for Removal of Methylene Blue in Water [J]. Chem. J. Chinese Universities, 2022, 43(6): 20220055.
[3]	WANG Hongning, HUANG Li, QING Jiang, MA Tengzhou, JIANG Wei, HUANG Weiqiu, CHEN Ruoyu. Activation of Biochar from Cattail and the VOCs Adsorption Application [J]. Chem. J. Chinese Universities, 2022, 43(4): 20210824.
[4]	CHEN Xiaolu, YUAN Zhenyan, ZHONG Yingchun, REN Hao. Preparation of Triphenylamine Based PAF-106s via Mechanical Ball Milling and C2 Hydrocarbons Adsorption Property [J]. Chem. J. Chinese Universities, 2022, 43(3): 20210771.
[5]	MENG Xianglong, YANG Ge, GUO Hailing, LIU Chenguang, CHAI Yongming, WANG Chunzheng, GUO Yongmei. Synthesis of Nano-zeolite and Its Adsorption Performance for Hydrogen Sulfide [J]. Chem. J. Chinese Universities, 2022, 43(3): 20210687.
[6]	TAN Lejian, ZHONG Xuanshu, WANG Jin, LIU Zongjian, ZHANG Aiying, YE Lin, FENG Zengguo. Low Critical Dissolution Temperature Behavior of β⁃Cyclodextrin and Its Application in the Preparation of β⁃Cyclodextrin Sheet Crystal with Ordered Nano⁃channel [J]. Chem. J. Chinese Universities, 2022, 43(11): 20220405.
[7]	ZHENG Meiqi, MAO Fangqi, KONG Xianggui, DUAN Xue. Layered Double Hydroxides as Sorbent for Remediation of Radioactive Wastewater [J]. Chem. J. Chinese Universities, 2022, 43(10): 20220456.
[8]	TIAN Xiaokang, ZHANG Qingsong, YANG Shulin, BAI Jie, CHEN Bingjie, PAN Jie, CHEN Li, WEI Yen. Porous Materials Inspired by Microbial Fermentation： Preparation Method and Application [J]. Chem. J. Chinese Universities, 2022, 43(10): 20220216.
[9]	ZHANG Chi, SUN Fuxing, ZHU Guangshan. Synthesis， N₂ Adsorption and Mixed-matrix Membrane Performance of Bimetal Isostructural CAU-21 [J]. Chem. J. Chinese Universities, 2022, 43(1): 20210578.
[10]	MA Jianxin, LIU Xiaodong, XU Na, LIU Guocheng, WANG Xiuli. A Multi-functional Zn（II） Coordination Polymer with Luminescence Sensing， Amperometric Sensing， and Dye Adsorption Performance [J]. Chem. J. Chinese Universities, 2022, 43(1): 20210585.
[11]	CHANG Shuqing, XIN Xu, HUANG Yaqi, ZHANG Xincong, FU Yanghe, ZHU Weidong, ZHANG Fumin, LI Xiaona. Pyroelectrically-induced Catalytic Performance of Zr-based MOF Under Cold-hot Alternation [J]. Chem. J. Chinese Universities, 2021, 42(8): 2558.
[12]	SU Yingli, REN Haisheng, LI Xiangyuan. Application of New Nonequilibrium Solvation Theory in Electronic Spectra of Organic Dyes [J]. Chem. J. Chinese Universities, 2021, 42(7): 2254.
[13]	LIU Changhui, LIANG Guojun, LI Yanlu, CHENG Xiufeng, ZHAO Xian. Density Functional Theory Study of NH₃ Adsorption on Boron Nanotubes [J]. Chem. J. Chinese Universities, 2021, 42(7): 2263.
[14]	WANG Hongning, HUANG Li, SONG Fujiao, ZHU Ting, HUANG Weiqiu, ZHONG Jing, CHEN Ruoyu. Synthesis and VOCs Adsorption Properties of Hollow Carbon Nanospheres [J]. Chem. J. Chinese Universities, 2021, 42(6): 1704.
[15]	WANG Longjie, FAN Hongchuan, QIN Yu, CAO Qiue, ZHENG Liyan. Research Progress of Metal-organic Frameworks in the Field of Chemical Separation and Analysis [J]. Chem. J. Chinese Universities, 2021, 42(4): 1167.