Synthesis， Structure and Characterization of a Dihydrophenazine Based 3D Covalent Organic Framework

doi:10.7503/cjcu20220210

Abstract

Abstract:

Dihydrophenazine derivatives have received considerable attention due to their unique redox activity. In this paper， a dihydrophenazine based monomer 5，10-di（4-formylphenyl）-5，10-dihydrophenazine（M1） was designed and synthesized， and 3D-PN-2 was then prepared with a Schiff-base reaction by the combination of M1 and tetrakis（4-aminophenyl）methane（TAM）. 3D-PN-2 was characterized by powder X-ray diffraction（PXRD）， nitrogen adsorption-desorption experiment， FTIR， ¹³C CP/MAS NMR， SEM and TEM. After combined with theoretical simulation， 3D-PN-2 was identified as a three-dimensional covalent organic framework（3D COF） with an 11-fold interpenetrated dia topology. Subsequent studies showed that 3D-PN-2 had good thermal and chemical stability. The optical absorption property of 3D-PN-2 was studied by UV-Vis diffuse reflectance spectrum. 3D-PN-2 exhibits broad absorption in the region from UV to visible light（absorption edge： 630 nm）， and the band gap of 3D-PN-2 is 2.11 eV. The redox property was studied by cyclic voltammetry， and the highest occupied molecular orbital（E_HOMO） and lowest unoccupied molecular orbital（E_LUMO） were calculated to be -4.50 and -2.39 eV， respectively. These results suggest that 3D-PN-2 will be a promising COF candidate for photocatalysis applications.

Key words: Covalent organic framework（COF）, Dihydrophenazine, Porous material

CLC Number:

O622

TrendMD:

WANG Kaixuan, LI Ziping, CHEN Xianyang, CUI Yong. Synthesis， Structure and Characterization of a Dihydrophenazine Based 3D Covalent Organic Framework[J]. Chem. J. Chinese Universities, 2022, 43(10): 20220210.

Figures/Tables 6

References 29

1	Ding S. Y.， Wang W.， Chem. Soc. Rev.， 2013， 42（2）， 548—568
2	Jiang D. L.， Chem.， 2020， 6（10）， 2461—2483
3	Lohse M. S.， Bein T.， Adv. Funct. Mater.， 2018， 28（33）， 1705553
4	Chen F. Q.， Guan X. Y.， Li H.， Ding J. H.， Zhu L. K.， Tang B.， Valtchev V.， Yan Y. S.， Qiu S. L.， Fang Q. R.， Angew. Chem. Int. Ed.， 2021， 60（41）， 22230—22235
5	Lyle S. J.， Waller P. J.， Yaghi O. M.， Trends Chem.， 2019， 1（2）， 172—184
6	Wang X. R.， Han X.， Zhang J.， Wu X. W.， Liu Y.， Cui Y.， J. Am. Chem. Soc.， 2016， 138（38）， 12332—12335
7	Wu X. W.， Han X.， Xu Q. S.， Liu Y. H.， Yuan C.， Yang S.， Liu Y.， Jiang J. W.， Cui Y.， J. Am. Chem. Soc.， 2019， 141（17）， 7081—7089
8	Yan Y. L.， Huang X. L.， Fan J.， Cai S. L.， Zheng S. R.， Zhang W. G.， Chem. J. Chinese Universities， 2020， 41（9）， 1996—2002
	严逸伦，黄晓玲，范军，蔡松亮，郑盛润，章伟光. 高等学校化学学报， 2020， 41（9）， 1996—2002
9	Wang K. X.， Kang X.， Yuan C.， Han X.， Liu Y.， Cui Y.， Angew. Chem. Int. Edit.， 2021， 60（35）， 19466—19476
10	Chen R. F.， Shi J. L.， Ma Y.， Lin G. Q.， Lang X. J.， Wang C.， Angew. Chem. Int. Ed.， 2019， 58（19）， 6430—6434
11	Wang X. Y.， Chen L. J.， Chong S. Y.， Little M. A.， Wu Y. Z.， Zhu W. H.， Clowes R.， Yan Y.， Zwijnenburg M. A.， Sprick R. S.， Cooper A. I.， Nat. Chem.， 2018， 10（12）， 1180—1189
12	Vitaku E.， Gannett C. N.， Carpenter K. L.， Shen L. X.， Abruna H. D.， Dichtel W. R.， J. Am. Chem. Soc.， 2020， 142（1）， 16—20
13	Wu M. M.， Zhao Y.， Zhao R. Q.， Zhu J.， Liu J.， Zhang Y. M.， Li C. X.， Ma Y. F.， Zhang H. T.， Chen Y. S.， Adv. Funct. Mater.， 2022， 32（11）， 2107703
14	Zhou T. Y.， Xu S. Q.， Wen Q.， Pang Z. F.， Zhao X.， J. Am. Chem. Soc.， 2014， 136（45）， 15885—15888
15	Zhu Y. L.， Wan S.， Jin Y. H.， Zhang W.， J. Am. Chem. Soc.， 2015， 137（43）， 13772—13775
16	Li X.， Yadav P.， Loh K. P.， Chem. Soc. Rev.， 2020， 49（14）， 4835—4866
17	Guan X. Y.， Chen F. Q.， Fang Q. R.， Qiu S. L.， Chem. Soc. Rev.， 2020， 49（5）， 1357—1384
18	Lu H. S.， Han W. K.， Yan X. D.， Chen C. J.， Niu T. F.， Gu Z. G.， Angew. Chem. Int. Ed.， 2021， 60（33）， 17881—17886
19	Zhang Y. Y.， Duan J. Y.， Ma D.， Li P. F.， Li S. W.， Li H. W.， Zhou J. W.， Ma X. J.， Feng X.， Wang B.， Angew. Chem. Int. Ed.， 2017， 56（51）， 16313—16317
20	Zhang L.， Yang L. L.， Wan S. C.， Yang Q. C.， Xiao Y.， Deng H. X.， Sun Z. J.， Nano. Lett.， 2021， 21（19）， 7979—7988
21	Jiang W. L.， Huang B.， Wu M. X.， Zhu Y. K.， Zhao X. L.， Shi X. L.， Yang H. B.， Chem. Asian J.， 2021， 16（23）， 3985—3992
22	Schorpp M.， Heizmann T.， Schmucker M.， Rein S.， Weber S.， Krossing I.， Angew. Chem. Int. Ed.， 2020， 59（24）， 9453—9459
23	Kwon G.， Lee S.， Hwang J.， Shim H. S.， Lee B.， Lee M. H.， Ko Y.， Jung S. K.， Ku K.， Hong J.， Kang K.， Joule， 2018， 2（9）， 1771—1782
24	Nagasaki J.， Hiroto S.， Shinokubo H.， Chem. Asian J.， 2017， 12（17）， 2311—2317
25	Theriot J. C.， Lim C. H.， Yang H.， Ryan M. D.， Musgrave C. B.， Miyake G. M.， Science， 2016， 352（6289）， 1082—1086
26	Wang B. S.， Li P.， Yu F. B.， Chen J. S.， Qu Z. J.， Han K. L.， Chem. Commun.， 2013， 49（51）， 5790—5792
27	Zhang Y. Y.， Li H.， Chang J. H.， Guan X. Y.， Tang L. X.， Fang Q. R.， Valtchev V.， Yan Y. S.， Qiu S. L.， Small， 2021， 17（22）， 2006112
28	Luo X. X.， Li W. H.， Liang H. J.， Zhang H. X.， Du K. D.， Wang X. T.， Liu X. F.， Zhang J. P.， Wu X. L.， Angew. Chem. Int. Ed.， 2022， 61（10）， e202117661
29	Wei P. F.， Qi M. Z.， Wang Z. P.， Ding S. Y.， Yu W.， Liu Q.， Wang L. K.， Wang H. Z.， An W. K.， Wang W.， J. Am. Chem. Soc.， 2018， 140（13）， 4623—4631

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