基于间苯三酚及其衍生物构筑新型有机多孔材料

doi:10.6023/cjoc202005070

摘要/Abstract

有机多孔材料凭借其高比表面积、孔道可调性、易功能化修饰和结构多样性等特征, 在催化、能源、吸附与分离等多个领域中展现了巨大应用潜力. 对多官能度有机化合物单体以及高效聚合反应的巧妙应用, 为新型有机多孔材料的创制提供了强有力的工具, 成为该领域的研究热点. 以C₃对称型的间苯三酚及其衍生物为例, 综述了其在一系列新型有机多孔材料高效构筑中的最新研究进展.

关键词: 间苯三酚, 多孔高分子材料, 金属有机框架, 共价有机框架, 功能化

Porous organic materials have found many applications, such as catalysis, energy, adsorption and separation., owing to the high specific surface area, pore channel tunability, easy functionalization and structural diversity. The careful selection of specific monomers with polyfunctionality and highly efficient polymerization provides powerful tools for creating novel porous organic materials, and it has become a research topic in this field. Herein the latest progress in the efficient construction of novel porous organic materials is reviewed taking C₃ symmetrical phloroglucinol and its derivatives as examples.

Key words: phoroglucinol, porous organic polymer, metal organic framework, covalent organic framework, functionalization

引用此文

邓汉林, 罗贤升, 李志华, 赵江颖, 黄木华. 基于间苯三酚及其衍生物构筑新型有机多孔材料[J]. 有机化学, 2021, 41(2): 624-641.

Hanlin Deng, Xiansheng Luo, Zhihua Li, Jiangying Zhao, Muhua Huang. Synthesis of Novel Porous Organic Materials Based on Phloroglucinol and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 624-641.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 17

图式1. 间苯三酚的合成与应用

Scheme 1. Synthesis and applications of phloroglucinol

图式2. 基于TFP发展的稳定化COFs材料

Scheme 2. Developing stable COFs based on TFP

图式3. 基于TAPG的稳定的COFs材料

Scheme 3. Developing COFs based on TAPG

图式4. C2N的合成

Scheme 4. Synthesis of C2N

图式5. COF-TT的合成

Scheme 5. Synthesis of COF-TT

图式6. Cage-COFs的合成

Scheme 6. Synthesis of cage-COFs

图式7. Cage-COFs结构

Scheme 7. Structures of cage-COFs

图式8. 基于间苯三酚衍生物的MOFs与配体

Scheme 8. MOFs and ligands based on derivatives of phloroglucinol

Entry	Polymer	S_BET/(m²?g^–1)	Mean pore size/nm	V_tot/(g?cm^–3)
1^[62]	CE-P2	195	3.39	0.198
2^[63]	CTF-IP10	358	—	0.22
3^[65]	COP-36	11	—	0.032
4^[66]	Si(OAc)₄-based	990	3.51	0.84
5^[66]	HSi(OAc)₃-based	933	5.99	1.36
6^[66]	MeSi(OAc)₃-based	455	2.73	0.285
7^[67]	BoxPOP-1	231	—	0.98
8^[67]	BoxPOP-2	225	—	0.74
9^[67]	BoxPOP-3	46	—	0.17
10^[68]	CPF-T	654	—	0.33

表1. 基于间苯三酚的O-功能化反应构筑POPs总结

Table 1. Summary of POPs based on O-functionalized reaction

图式9. 基于间苯三酚O-功能化反应的POPs

Scheme 9. POPs based on O-functionalized reactions

图式10. 基于醛基缩合反应的POPs

Scheme 10. POPs based on aldehyde condensation reactions

Entry	Polymer	S_BET/(m²?g^–1)	Mean pore size/nm	V_tot/(g?cm^–3)
1^[69]	POF1B, POF1A	917, 773	0.6	—
2^[69]	POF2B, POF2A	769, 658	0.6	—
3^[69]	POF3B, POF3A	608, 115	0.6, —	—
4^[70]	MesoPOF-1	1027	—	0.86
5^[71]	PRP-1	835	—	—
6^[73]	POF-1S	29	—	—
7^[72]	PTF-Cr	106	—	—
8^[72]	PTF-Mg	128	—	—
9^[74]	POF-1ES	57	—	—
10^[76]	HROP	568	—	0.80

表2. 基于醛基缩合反应的POPs总结

Table 2. Summary of POPs based on aldehyde condensation reactions

图式11. 基于重氮偶联反应的POPs

Scheme 11. POPs based on azo coupling reactions

Entry	Polymer	S_BET/(m²?g^–1)	Mean pore size/nm	V_tot/(g?cm^–3)
1^[77]	HAzo-POP-1	256	—	1.325
2^[77]	HAzo-POP-3	418	—	1.730
3^[79]	Co^Ⅱ-NDI-PG, NDI-PG	88, 93	—	—
4^[80]	Ag@AzoTPE-CMP, AzoTPE-CMP	47, 366	—	0.110, 1.072
5^[81]	TAP1	474	—	0.74
6^[81]	TAP2	772	—	1.41
7^[81]	TAP3	729	—	1.04
8^[22]	TKH-POP-2	437	—	1.4
9^[22]	TKH-POP-3	552	—	2.3
10^[22]	TKH-POP-4	639	—	2.2

表3. 基于重氮偶联反应的POPs总结

Table 3. Summary of POPs based on azo coupling reactions

图式12. 基于Friedel-Craft反应的POPs

Scheme 12. POPs based on Friedel-Craft reactions

图式13. 基于间苯三酚衍生物聚合反应的POPs

Scheme 13. POPs based on polymerization of derivatives of phloroglucinol

Entry	Polymer	S_BET/ (m²?g^–1)	Mean pore size/nm	V_tot/ (g?cm^–3)
1^[84]	PAF-18 PAF-18-OLi	1121 982	1.33 1.32	0.82 0.70
2^[85]	PAF-34-OH	771	—	—
3^[86]	PAF-80	768	—	—
4^[87]	TpPAM	654	1.6	0.23
5^[88]	TPDA-1	545	—	0.255
6^[89]	TrzPOP-3	772	—	—
7^[90]	SNP-BTT-1	698	—	—
8^[90]	SNP-BTT-2	411	—	—
9^[61]	Azo-POP-4	368	25.7	1.809
10^[61]	Azo-POP-5	196	38.2	1.784
11^[61]	Azo-POP-6	210	35.0	1.776

表4. 基于间苯三酚衍生物聚合反应POPs总结

Table 4. Summary of POPs based on polymerization of derivatives of phloroglucinol

参考文献 91

[1]	Sanna C.; Scognamiglio M.; Fiorentino A.; Corona A.; Graziani V.; Caredda A.; Cortis P.; Montisci M.; Ceresola E.R.; Canducci F.; Poli F.; Tramontano E.; Esposito F. PLoS One 2018, 13, e195168.
[2]	Broadley K.; Larsen L.; Herst P.M.; Smith R. A. J.; Berridge M.V.; Mcconnell M.J. J. Cell Biochem. 2011, 112, 1869. doi: 10.1002/jcb.23107
[3]	Zhang B.X.; Duan D.Z.; Ge C.P.; Yao J.P.; Liu Y.P.; Li X.M.; Fang J.G. J. Med. Chem. 2015, 58, 1795. doi: 10.1021/jm5016507
[4]	Bellamy A.J.; Ward S.J.; Golding P. Propellants, Explos., Pyrotech. 2002, 27, 49. doi: 10.1002/1521-4087(200204)27:2【-逻辑与-】amp;lt;49::AID-PREP49【-逻辑与-】amp;gt;3.0.CO;2-4
[5]	Wurzenberger M. H. H.; Bissinger B. R. G.; Lommel M.; Gruhne M.S.; Szimhardt N.; Stierstorfer J. New J. Chem. 2019, 43, 18193. doi: 10.1039/c9nj03937f pmid: WOS:000499476200033
[6]	Liang C.D.; Dai S. J. Am. Chem. Soc. 2006, 128, 5316. doi: 10.1021/ja060242k
[7]	Yuan F.L.; Yuan T.S.; Sui L.Z.; Wang Z.B.; Xi Z.F.; Li Y.C.; Li X.H.; Fan L.Z.; Tan Z.A.; Chen A.M.; Jin M.X.; Yang S.H. Nat. Commun. 2018, 9, 2249. doi: 10.1038/s41467-018-04635-5
[8]	Tsyurupa M.P.; Davankov V.A. React. Funct. Polym. 2002, 53, 193. doi: 10.1016/S1381-5148(02)00173-6
[9]	Wang S.; Song K.; Zhang C.; Shu Y.; Li T.; Tan B. J. Mater. Chem. A 2017, 5, 1509. doi: 10.1039/C6TA08556C
[10]	Tan L.X.; Tan B.E. Chem. Soc. Rev. 2017, 46, 3322. doi: 10.1039/C6CS00851H
[11]	Chen L.; Honsho Y.; Seki S.; Jiang D.L. J. Am. Chem. Soc. 2010, 132, 6742. doi: 10.1021/ja100327h
[12]	Dawson R.; Adams D.J.; Cooper A.I. Chem. Sci. 2011, 2, 1173. doi: 10.1039/c1sc00100k
[13]	Yuan K.; Guo-Wang P.; Hu T.; Shi L.; Zeng R.; Forster M.; Pichler T.; Chen Y.W.; Scherf U. Chem. Mater. 2015, 27, 7403. doi: 10.1021/acs.chemmater.5b03290
[14]	Budd P.M.; Msayib K.J.; Tattershall C.E.; Ghanem B.S.; Reynolds K.J.; Mckeown N.B.; Fritsch D. J. Membr. Sci. 2005, 251, 263. doi: 10.1016/j.memsci.2005.01.009
[15]	Rose I.; Bezzu C.G.; Carta M.; Comesana-Gandara B.; La- sseuguette E.; Ferrari M.C.; Bernardo P.; Clarizia G.; Fuoco A.; Jansen J.C.; Hart K.E.; Liyana-Arachchi T.P.; Colina C.M.; Mckeown N.B. Nat. Mater. 2017, 16, 932. doi: 10.1038/nmat4939 pmid: 28759030
[16]	Ben T.; Ren H.; Ma S.Q.; Cao D.P.; Lan J.H.; Jing X.F.; Wang W.C.; Xu J.; Deng F.; Simmons J.M.; Qiu S.L.; Zhu G.S. Angew. Chem., Int. Ed. 2009, 48, 9457, S9451. doi: 10.1002/anie.200904637
[17]	Ben T.; Qiu S.L. CrystEngComm 2013, 15, 17. doi: 10.1039/C2CE25409C
[18]	Jiang L.C.; Tian Y.Y.; Sun T.; Zhu Y.L.; Ren H.; Zou X.Q.; Ma Y.H.; Meihaus K.R.; Long J.R.; Zhu G.S. J. Am. Chem. Soc. 2018, 140, 15724. doi: 10.1021/jacs.8b08174
[19]	Hei Z.; Huang M.; Luo Y.; Wang Y. Polym. Chem. 2016, 7, 770. doi: 10.1039/C5PY01682G
[20]	Fu H.X.; Zhang Z.H.; Fan W.H.; Wang S.F.; Liu Y.; Huang M.H. J. Mater. Chem. A 2019, 7, 15048. doi: 10.1039/C9TA04594E
[21]	Chen Q.; Luo M.; Hammershoej P.; Zhou D.; Han Y.; Laursen B.W.; Yan C.G.; Han B.H. J. Am. Chem. Soc. 2012, 134, 6084. doi: 10.1021/ja300438w
[22]	Liu X.X.; Luo X.S.; Fu H.X.; Fan W.H.; Chen S.L.; Huang M.H. Chem. Commun. 2020, 56, 2103. doi: 10.1039/C9CC09710D
[23]	Cote A.P.; Benin A.I.; Ockwig N.W.; O'Keeffe M.; Matzger A.J.; Yaghi O.M. Science 2005, 310, 1166. doi: 10.1126/science.1120411
[24]	Yaghi O.M.; Li G.M.; Li H.L. Nature 1995, 378, 703. doi: 10.1038/378703a0
[25]	Kandambeth S.; Dey K.; Banerjee R. J. Am. Chem. Soc. 2019, 141, 1807. doi: 10.1021/jacs.8b10334 pmid: WOS:000458348300002
[26]	Kandambeth S.; Mallick A.; Lukose B.; Mane M.V.; Heine T.; Banerjee R. J. Am. Chem. Soc. 2012, 134, 19524. doi: 10.1021/ja308278w
[27]	Chandra S.; Kandambeth S.; Biswal B.P.; Lukose B.; Kunjir S.M.; Chaudhary M.; Babarao R.; Heine T.; Banerjee R. J. Am. Chem. Soc. 2013, 135, 17853. doi: 10.1021/ja408121p
[28]	Biswal B.P.; Chandra S.; Kandambeth S.; Lukose B.; Heine T.; Banerjee R. J. Am. Chem. Soc. 2013, 135, 5328. doi: 10.1021/ja4017842
[29]	Pachfule P.; Kandambeth S.; Diaz D.; Banerjee R. Chem. Commun. 2014, 50, 3169. doi: 10.1039/C3CC49176E
[30]	Biswal B.P.; Kandambeth S.; Chandra S.; Shinde D.B.; Bera S.; Karak S.; Garai B.; Kharul U.K.; Banerjee R. J. Mater. Chem. A 2015, 3, 23664. doi: 10.1039/C5TA07998E
[31]	Deblase C.R.; Silberstein K.E.; Truong T.; Abruña H.D.; Dichtel W.R. J. Am. Chem. Soc. 2013, 135, 16821. doi: 10.1021/ja409421d
[32]	Deblase C.R.; Hernandez-Burgos K.; Silberstein K.E.; Rodriguez-Calero G.G.; Bisbey R.P.; Abruna H.D.; Dichtel W.R. ACS Nano. 2015, 9, 3178. doi: 10.1021/acsnano.5b00184
[33]	Mulzer C.R.; Shen L.X.; Bisbey R.P.; Mckone J.R.; Zhang N.; Abruna H.D.; Dichtel W.R. ACS Cent. Sci. 2016, 2, 667. doi: 10.1021/acscentsci.6b00220
[34]	Vitaku E.; Gannett C.N.; Carpenter K.L.; Shen L.X.; Abruna H.D.; Dichtel W.R. J. Am. Chem. Soc. 2020, 142, 16. doi: 10.1021/jacs.9b08147
[35]	Li Z.P.; Zhi Y.F.; Feng X.; Ding X.S.; Zou Y.C.; Liu X.M.; Mu Y. Chem.-Eur. J. 2015, 21, 12079. doi: 10.1002/chem.v21.34
[36]	Yang H.; Wu H.; Yao Z.Q.; Shi B.B.; Xu Z.; Cheng X.X.; Pan F.S.; Liu G.H.; Jiang Z.Y.; Cao X.Z. J. Mater. Chem. A 2018, 6, 583. doi: 10.1039/C7TA09596A
[37]	Yang H.; Wu H.; Xu Z.; Mu B.W.; Lin Z.X.; Cheng X.X.; Liu G.H.; Pan F.S.; Cao X.Z.; Jiang Z.Y. J. Membr. Sci. 2018, 561, 79. doi: 10.1016/j.memsci.2018.05.036
[38]	Liu G.H.; Jiang Z.Y.; Yang H.; Li C.D.; Wang H.J.; Wang M.D.; Song Y.M.; Wu H.; Pan F.S. J. Membr. Sci. 2019, 572, 557. doi: 10.1016/j.memsci.2018.11.040
[39]	Wang M.D.; Pan F.S.; Yang H.; Cao Y.; Wang H.J.; Song Y.M.; Lu Z.; Sun M.Z.; Wu H.; Jiang Z.Y. J. Mater. Chem. A 2019, 7, 9912. doi: 10.1039/C8TA11883C
[40]	Cantillo D.; Damm M.; Dallinger D.; Bauser M.; Berger M.; Kappe C.O. Org. Process Res. Dev. 2014, 18, 1360. doi: 10.1021/op5001435
[41]	Seo J.M.; Noh H.; Jeong H.Y.; Baek J.B. J. Am. Chem. Soc. 2019, 141, 11786. doi: 10.1021/jacs.9b05244
[42]	Mahmood J.; Lee E.K.; Jung M.; Shin D.; Jeon I.Y.; Jung S.M.; Choi H.J.; Seo J.M.; Bae S.Y.; Sohn S.D.; Park N.; Oh J.H.; Shin H.J.; Baek J.B. Nat. Commun. 2015, 6, 6486. doi: 10.1038/ncomms7486 pmid: 25744355
[43]	Mahmood J.; Jung S.; Kim S.; Park J.; Yoo J.; Baek J. Chem. Mater. 2015, 27, 4860. doi: 10.1021/acs.chemmater.5b01734
[44]	Mahmood J.; Li F.; Jung S.M.; Okyay M.S.; Ahmad I.; Kim S.J.; Park N.; Jeong H.Y.; Baek J.B. Nat. Nanotechnol. 2017, 12, 441. doi: 10.1038/nnano.2016.304 pmid: 28192390
[45]	Mahmood J.; Li F.; Kim C.; Choi H.J.; Gwon O.; Jung S.M.; Seo J.M.; Cho S.J.; Ju Y.W.; Jeong H.Y.; Kim G.; Baek J.B. Nano Energy 2018, 44, 304. doi: 10.1016/j.nanoen.2017.11.057
[46]	Walczak R.; Kurpil B.; Savateev A.; Heil T.; Schmidt J.; Qin Q.; Antonietti M.; Oschatz M. Angew. Chem., Int. Ed. 2018, 57, 10765. doi: 10.1002/anie.v57.33
[47]	Shinde S.S.; Lee C.H.; Yu J.; Kim D.; Lee S.U.; Lee J. ACS Nano. 2018, 12, 596. doi: 10.1021/acsnano.7b07473
[48]	Li M.; Cui Z.; Pang S.; Meng L.; Ma D.; Li Y.; Shi Z.; Feng S. J. Mater. Chem. C 2019, 7, 11919.
[49]	Ma J.X.; Li J.; Chen Y.F.; Ning R.; Ao Y.F.; Liu J.M.; Sun J.L.; Wang D.X.; Wang Q.Q. J. Am. Chem. Soc. 2019, 141, 3843. doi: 10.1021/jacs.9b00665
[50]	Yang Y.; He X.Y.; Zhang P.H.; Andaloussi Y.H.; Zhang H.L.; Jiang Z.Y.; Chen Y.; Ma S.Q.; Cheng P.; Zhang Z.J. Angew. Chem., Int. Ed. 2020, 59, 3678. doi: 10.1002/anie.v59.9
[51]	Abrahams B.F.; Egan S.J., Robson R. J. Am. Chem. Soc. 1999, 121, 3535. doi: 10.1021/ja990016t
[52]	Hurd J.A.; Vaidhyanathan R.; Thangadurai V.; Ratcliffe C.I.; Moudrakovski I.L.; Shimizu G. K. H.Nat. Chem. 2009, 1, 705. doi: 10.1038/nchem.402
[53]	Kim S.R.; Dawson K.W.; Gelfand B.S.; Taylor J.M.; Shimizu G. K. H.J. Am. Chem. Soc. 2013, 135, 963. doi: 10.1021/ja310675x
[54]	Yang R.; Li L.; Xiong Y.; Li J.; Zhou H.C.; Su C.Y. Chem.- Asian J. 2010, 5, 2358. doi: 10.1002/asia.v5:11
[55]	Zhao N.N.; Li W. J.; Sun C.Y.; Bian Y.Z.; Wang H.L.; Chang Z.D.; Fan H.X. Solid State Sci. 2012, 14, 317. doi: 10.1016/j.solidstatesciences.2011.12.014
[56]	Chaudhari A.K.; Nagarkar S.S.; Joarder B.; Ghosh S.K. Cryst. Growth Des. 2013, 13, 3716. doi: 10.1021/cg400749m
[57]	Rimoldi M.; Nakamura A.; Vermeulen N.A.; Henkelis J.J.; Blackburn A.K.; Hupp J.T.; Stoddart J.F.; Farha O.K. Chem. Sci. 2016, 7, 4980. doi: 10.1039/C6SC01376G
[58]	Hong S.; Rohman M.R.; Jia J.T.; Kim Y.; Moon D.; Kim Y.; Ko Y.H.; Lee E.; Kim K. Angew. Chem., Int. Ed. 2015, 54, 13241. doi: 10.1002/anie.v54.45
[59]	Chen Q.; Luo M.; Hammershoej P.; Zhou D.; Han Y.; Laursen B.W.; Yan C.G.; Han B.H. J. Am. Chem. Soc. 2012, 134, 6084. doi: 10.1021/ja300438w
[60]	Zhou J.X.; Luo X.S.; Liu X.X.; Qiao Y.; Wang P.F.; Mecerreyes D.; Bogliotti N.; Chen S.L.; Huang M.H. J. Mater. Chem. A 2018, 6, 5608. doi: 10.1039/C8TA00341F
[61]	Liu X.X.; Luo X.S.; Deng H.L.; Fan W.H.; Wang S.F.; Yang C.J.; Sun X.Y.; Chen S.L.; Huang M.H. Chem. Mater. 2019, 31, 5421. doi: 10.1021/acs.chemmater.9b00590
[62]	Yu H.; Shen C.J.; Wang Z.G. ChemPlusChem 2013, 78, 498. doi: 10.1002/cplu.201300090
[63]	Karmakar A.; Kumar A.; Chaudhari A.K.; Samanta P.; Desai A.V.; Krishna R.; Ghosh S.K. Chem.-Eur. J. 2016, 22, 4931. doi: 10.1002/chem.201600109
[64]	Wang L.; Jia J.T.; Faheem M.; Tian Y.Y.; Zhu G.S. J. Ind. Eng. Chem. 2018, 67, 373. doi: 10.1016/j.jiec.2018.07.011
[65]	Ullah R.; Atilhan M.; Anaya B.; Al-Muhtaseb S.; Aparicio S.; Patel H.; Thirion D.; Yavuz C.T. ACS Appl. Mater. Interfaces 2016, 8, 20772. doi: 10.1021/acsami.6b05927
[66]	Kejik M.; Moravec Z.; Barnes C.E.; Pinkas J. Microporous Mesoporous Mater. 2017, 240, 205. doi: 10.1016/j.micromeso.2016.11.012
[67]	Xu S.J.; He J.; Jin S.B.; Tan B.E. J. Colloid Interface Sci. 2018, 509, 457. doi: 10.1016/j.jcis.2017.09.009
[68]	Zhang M.C.; Li Y.; Bai C.Y.; Guo X.H.; Han J.; Hu S.; Jiang H.Q.; Tan W.; Li S.J.; Ma L.J. ACS Appl. Mater. Interfaces 2018, 10, 28936. doi: 10.1021/acsami.8b06842
[69]	Katsoulidis A.P.; Kanatzidis M.G. Chem. Mater. 2011, 23, 1818. doi: 10.1021/cm103206x
[70]	Katsoulidis A.P.; Kanatzidis M.G. Chem. Mater. 2012, 24, 471. doi: 10.1021/cm202578k
[71]	Ding M.L.; Jiang H.L. Chem. Commun. 2016, 52, 12294. doi: 10.1039/C6CC07149J
[72]	Pareek K.; Rohan R.; Chen Z.; Zhao D.; Cheng H.S. Int. J. Hydrogen Energy 2017, 42, 6801. doi: 10.1016/j.ijhydene.2017.01.209
[73]	Kang D.W.; Lim K.S.; Lee K.J.; Lee J.H.; Lee W.R.; Song J.H.; Yeom K.H.; Kim J.Y.; Hong C.S. Angew. Chem., Int. Ed. 2016, 55, 16123. doi: 10.1002/anie.201609049
[74]	Kang D.W.; Song J.H.; Lee K.J.; Lee H.G.; Kim J.E.; Lee H.Y.; Kim J.Y.; Hong C.S. J. Mater. Chem. A 2017, 5, 17492. doi: 10.1039/C7TA05279K
[75]	Kang D.W.; Lee K.A.; Kang M.; Kim J.M.; Moon M.; Choe J.H.; Kim H.; Kim D.W.; Kim J.Y.; Hong C.S. J. Mater. Chem. A 2020, 8, 1147. doi: 10.1039/C9TA06807D
[76]	Chen T.T.; Tan H.L.; Chen Q.B.; Gu L.N..; Wei Z.S.; Liu H.L. ACS Appl. Mater. Interfaces 2019, 11, 48402. doi: 10.1021/acsami.9b17657
[77]	Ji G.P.; Yang Z.Z.; Zhang H.Y.; Zhao Y.F.; Yu B.; Ma Z.S.; Liu Z.M. Angew. Chem., Int. Ed. 2016, 55, 9685. doi: 10.1002/anie.201602667
[78]	Huang L.; He M.; Chen B.; Cheng Q.; Hu B. ACS Sustainable Chem. Eng. 2017, 5, 4050. doi: 10.1021/acssuschemeng.7b00031
[79]	Bhat S.A.; Das C.; Maji T.K. J. Mater. Chem. A 2018, 6, 19834. doi: 10.1039/C8TA06588H
[80]	Liu M.; Yao C.; Liu C.; Xu Y. Sci. Rep. 2018, 8, 14072. doi: 10.1038/s41598-018-32383-5
[81]	Bera R.; Ansari M.; Alam A.; Das N. ACS Appl. Polym. Mater. 2019, 1, 959. doi: 10.1021/acsapm.8b00264
[82]	Vinodh R.; Abidov A.; Peng M.M.; Babu C.M.; Palanichamy M.; Cha W.S.; Jang H. J. Ind. Eng. Chem. 2015, 32, 273. doi: 10.1016/j.jiec.2015.09.002
[83]	Jiang K.; Zhao H.R.; Dai J.X.; Kuang D.; Fei T.; Zhang T. ACS Appl. Mater. Interfaces 2016, 8, 25529. doi: 10.1021/acsami.6b08071
[84]	Ma H.P.; Ren H.; Zou X.Q; Sun F.X.; Yan Z.J.; Cai K.; Wang D.Y.; Zhu G.S. J. Mater. Chem. A 2013, 1, 752. doi: 10.1039/C2TA00616B
[85]	Yuan R.R.; Ren H.; Yan Z.J.; Wang A.F.; Zhu G.S. Polym. Chem. 2014, 5, 2266. doi: 10.1039/c3py01252b
[86]	Shen X.S.; Faheem M.; Matsuo Y.; Aziz S.; Zhang X.; Li Y.H.; Song J.; Tian Y.Y.; Zhu G.S. J. Mater. Chem. A 2019, 7, 2507. doi: 10.1039/C8TA11343B
[87]	Patra B.C.; Khilari S.; Manna R.N.; Mondal S.; Pradhan D.; Pradhan A.; Bhaumik A. ACS Catal. 2017, 7, 6120. doi: 10.1021/acscatal.7b01067
[88]	Bhanja P.; Das S.K.; Bhunia K.; Pradhan D.; Hayashi T.; Hijikata Y.; Irle S.; Bhaumik A. ACS Sustainable Chem. Eng. 2017, 6, 202. doi: 10.1021/acssuschemeng.7b02234
[89]	Das S.K.; Bhanja P.; Kundu S.K.; Mondal S.; Bhaumik A. ACS Appl. Mater. Interfaces 2018, 10, 23813. doi: 10.1021/acsami.8b05849
[90]	Kochergin Y.S.; Schwarz D.; Acharjya A.; Ichangi A.; Kulkarni R.; Eliášová P.; Vacek J.; Schmidt J.; Thomas A.; Bojdys M.J. Angew. Chem., Int. Ed. 2018, 57, 14188. doi: 10.1002/anie.201809702
[91]	Kochergin Y.S.; Noda Y.; Kulkarni R.; Akodáková K.; Tarábek J.; Schmidt J.; Bojdys M.J. Macromolecules 2019, 52, 7696. doi: 10.1021/acs.macromol.9b01643 pmid: WOS:000492801000017