Chinese Journal of Organic Chemistry >
Synthesis of Novel Porous Organic Materials Based on Phloroglucinol and Its Derivatives
Received date: 2020-05-26
Revised date: 2020-07-09
Online published: 2020-09-09
Supported by
the National Natural Science Foundation of China(21772013); the Natural Science Foundation of Beijing(2202049)
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.
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 . DOI: 10.6023/cjoc202005070
| [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. |
| [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. |
| [4] | Bellamy A.J.; Ward S.J.; Golding P. Propellants, Explos., Pyrotech. 2002, 27, 49. |
| [5] | Wurzenberger M. H. H.; Bissinger B. R. G.; Lommel M.; Gruhne M.S.; Szimhardt N.; Stierstorfer J. New J. Chem. 2019, 43, 18193. |
| [6] | Liang C.D.; Dai S. J. Am. Chem. Soc. 2006, 128, 5316. |
| [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. |
| [8] | Tsyurupa M.P.; Davankov V.A. React. Funct. Polym. 2002, 53, 193. |
| [9] | Wang S.; Song K.; Zhang C.; Shu Y.; Li T.; Tan B. J. Mater. Chem. A 2017, 5, 1509. |
| [10] | Tan L.X.; Tan B.E. Chem. Soc. Rev. 2017, 46, 3322. |
| [11] | Chen L.; Honsho Y.; Seki S.; Jiang D.L. J. Am. Chem. Soc. 2010, 132, 6742. |
| [12] | Dawson R.; Adams D.J.; Cooper A.I. Chem. Sci. 2011, 2, 1173. |
| [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. |
| [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. |
| [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. |
| [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. |
| [17] | Ben T.; Qiu S.L. CrystEngComm 2013, 15, 17. |
| [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. |
| [19] | Hei Z.; Huang M.; Luo Y.; Wang Y. Polym. Chem. 2016, 7, 770. |
| [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. |
| [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. |
| [22] | Liu X.X.; Luo X.S.; Fu H.X.; Fan W.H.; Chen S.L.; Huang M.H. Chem. Commun. 2020, 56, 2103. |
| [23] | Cote A.P.; Benin A.I.; Ockwig N.W.; O'Keeffe M.; Matzger A.J.; Yaghi O.M. Science 2005, 310, 1166. |
| [24] | Yaghi O.M.; Li G.M.; Li H.L. Nature 1995, 378, 703. |
| [25] | Kandambeth S.; Dey K.; Banerjee R. J. Am. Chem. Soc. 2019, 141, 1807. |
| [26] | Kandambeth S.; Mallick A.; Lukose B.; Mane M.V.; Heine T.; Banerjee R. J. Am. Chem. Soc. 2012, 134, 19524. |
| [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. |
| [28] | Biswal B.P.; Chandra S.; Kandambeth S.; Lukose B.; Heine T.; Banerjee R. J. Am. Chem. Soc. 2013, 135, 5328. |
| [29] | Pachfule P.; Kandambeth S.; Diaz D.; Banerjee R. Chem. Commun. 2014, 50, 3169. |
| [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. |
| [31] | Deblase C.R.; Silberstein K.E.; Truong T.; Abru?a H.D.; Dichtel W.R. J. Am. Chem. Soc. 2013, 135, 16821. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [40] | Cantillo D.; Damm M.; Dallinger D.; Bauser M.; Berger M.; Kappe C.O. Org. Process Res. Dev. 2014, 18, 1360. |
| [41] | Seo J.M.; Noh H.; Jeong H.Y.; Baek J.B. J. Am. Chem. Soc. 2019, 141, 11786. |
| [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. |
| [43] | Mahmood J.; Jung S.; Kim S.; Park J.; Yoo J.; Baek J. Chem. Mater. 2015, 27, 4860. |
| [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. |
| [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. |
| [46] | Walczak R.; Kurpil B.; Savateev A.; Heil T.; Schmidt J.; Qin Q.; Antonietti M.; Oschatz M. Angew. Chem., Int. Ed. 2018, 57, 10765. |
| [47] | Shinde S.S.; Lee C.H.; Yu J.; Kim D.; Lee S.U.; Lee J. ACS Nano. 2018, 12, 596. |
| [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. |
| [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. |
| [51] | Abrahams B.F.; Egan S.J., Robson R. J. Am. Chem. Soc. 1999, 121, 3535. |
| [52] | Hurd J.A.; Vaidhyanathan R.; Thangadurai V.; Ratcliffe C.I.; Moudrakovski I.L.; Shimizu G. K. H.Nat. Chem. 2009, 1, 705. |
| [53] | Kim S.R.; Dawson K.W.; Gelfand B.S.; Taylor J.M.; Shimizu G. K. H.J. Am. Chem. Soc. 2013, 135, 963. |
| [54] | Yang R.; Li L.; Xiong Y.; Li J.; Zhou H.C.; Su C.Y. Chem.- Asian J. 2010, 5, 2358. |
| [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. |
| [56] | Chaudhari A.K.; Nagarkar S.S.; Joarder B.; Ghosh S.K. Cryst. Growth Des. 2013, 13, 3716. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [62] | Yu H.; Shen C.J.; Wang Z.G. ChemPlusChem 2013, 78, 498. |
| [63] | Karmakar A.; Kumar A.; Chaudhari A.K.; Samanta P.; Desai A.V.; Krishna R.; Ghosh S.K. Chem.-Eur. J. 2016, 22, 4931. |
| [64] | Wang L.; Jia J.T.; Faheem M.; Tian Y.Y.; Zhu G.S. J. Ind. Eng. Chem. 2018, 67, 373. |
| [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. |
| [66] | Kejik M.; Moravec Z.; Barnes C.E.; Pinkas J. Microporous Mesoporous Mater. 2017, 240, 205. |
| [67] | Xu S.J.; He J.; Jin S.B.; Tan B.E. J. Colloid Interface Sci. 2018, 509, 457. |
| [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. |
| [69] | Katsoulidis A.P.; Kanatzidis M.G. Chem. Mater. 2011, 23, 1818. |
| [70] | Katsoulidis A.P.; Kanatzidis M.G. Chem. Mater. 2012, 24, 471. |
| [71] | Ding M.L.; Jiang H.L. Chem. Commun. 2016, 52, 12294. |
| [72] | Pareek K.; Rohan R.; Chen Z.; Zhao D.; Cheng H.S. Int. J. Hydrogen Energy 2017, 42, 6801. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [78] | Huang L.; He M.; Chen B.; Cheng Q.; Hu B. ACS Sustainable Chem. Eng. 2017, 5, 4050. |
| [79] | Bhat S.A.; Das C.; Maji T.K. J. Mater. Chem. A 2018, 6, 19834. |
| [80] | Liu M.; Yao C.; Liu C.; Xu Y. Sci. Rep. 2018, 8, 14072. |
| [81] | Bera R.; Ansari M.; Alam A.; Das N. ACS Appl. Polym. Mater. 2019, 1, 959. |
| [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. |
| [83] | Jiang K.; Zhao H.R.; Dai J.X.; Kuang D.; Fei T.; Zhang T. ACS Appl. Mater. Interfaces 2016, 8, 25529. |
| [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. |
| [85] | Yuan R.R.; Ren H.; Yan Z.J.; Wang A.F.; Zhu G.S. Polym. Chem. 2014, 5, 2266. |
| [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. |
| [87] | Patra B.C.; Khilari S.; Manna R.N.; Mondal S.; Pradhan D.; Pradhan A.; Bhaumik A. ACS Catal. 2017, 7, 6120. |
| [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. |
| [89] | Das S.K.; Bhanja P.; Kundu S.K.; Mondal S.; Bhaumik A. ACS Appl. Mater. Interfaces 2018, 10, 23813. |
| [90] | Kochergin Y.S.; Schwarz D.; Acharjya A.; Ichangi A.; Kulkarni R.; Eliá?ová P.; Vacek J.; Schmidt J.; Thomas A.; Bojdys M.J. Angew. Chem., Int. Ed. 2018, 57, 14188. |
| [91] | Kochergin Y.S.; Noda Y.; Kulkarni R.; Akodáková K.; Tarábek J.; Schmidt J.; Bojdys M.J. Macromolecules 2019, 52, 7696. |
/
| 〈 |
|
〉 |