Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface

Shaofei Wu; Hoa Phan; Jing Li; Haomin Xu; Xing Li; Dingguan Wang; Tun Seng Herng; Yi Han; Andrew Wee; Jun Ding; Jiong Lu; Jishan Wu

doi:10.1055/s-0041-1723767

Organic Materials, Table of Contents

CC BY-NC-ND 4.0 · Organic Materials 2021; 03(01): 060-066
DOI: 10.1055/s-0041-1723767

Energy Materials in the Age of Globalization

Original Article

Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface

Shaofei Wu

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Hoa Phan

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Jing Li

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Haomin Xu

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Xing Li

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Dingguan Wang

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Tun Seng Herng

^bDepartment of Materials Science & Engineering, National University of Singapore, 119260, Singapore

,

Yi Han

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Andrew Wee

^cDepartment of Physics, National University of Singapore, 2 Science Drive 3, 117542, Singapore

,

Jun Ding

^bDepartment of Materials Science & Engineering, National University of Singapore, 119260, Singapore

,

Jiong Lu

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

,

Jishan Wu

^aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore

^dJoint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, China

› Author Affiliations

Abstract

All articles of this category

Abstract

The construction of conjugated covalent organic frameworks (COFs) with strong C–C bond linkage remains a big challenge. Herein, we report a new strategy by using an oxidative C–C coupling reaction between electron-rich pyrrole rings at a liquid–liquid interface. Two threefold symmetric monomers containing three terminal pyrrole units were tested, and both gave two-dimensional conjugated COF films with good crystallinity. The bipyrrole units in the as-formed COFs are partially doped, which can be reduced to the neutral form by hydrazine and redoped by I₂ vapor. The I₂-doped films showed high conductivity (1.35 S/m). Meanwhile, the unpaired electrons exhibited moderate interlayer antiferromagnetic coupling.

Key words

covalent organic frameworks - oxidative C–C coupling - liquid–liquid interfaces - conducting polymers - polypyrroles

Full Text

References

References

1a Côté AP, Benin AI, Ockwig NW, O'Keeffe M, Matzger AJ, Yaghi OM. Science 2005; 310: 1166
1b Feng X, Ding X, Jiang D. Chem. Soc. Rev. 2012; 41: 6010
1c Ding SY, Wang W. Chem. Soc. Rev. 2013; 42: 548
1d Segura JL, Mancheño MJ, Zamora F. Chem. Soc. Rev. 2016; 45: 5635
1e Huang N, Wang P, Jiang DL. Nat. Rev. Mater. 2016; 1: 16068
1f Jin YH, Hu YM, Zhang W. Nat. Rev. Mater. 2017; 1: 0056
1g Kandambeth S, Dey K, Banerjee R. J. Am. Chem. Soc. 2019; 141: 1807

2a Kandambeth S, Mallick A, Lukose B, Mane MV, Heine T, Banerjee R. J. Am. Chem. Soc. 2012; 134: 19524
2b Xu H, Gao J, Jiang D. Nat. Chem. 2015; 7: 905
2c Bunck DN, Dichtel WR. J. Am. Chem. Soc. 2013; 135: 14952

3a Waller PJ, Lyle SJ, Osborn Popp TM, Diercks CS, Reimer JA, Yaghi OM. J. Am. Chem. Soc. 2016; 138: 15519
3b Li X, Zhang C, Cai S, Lei X, Altoe V, Hong F, Urban JJ, Ciston J, Chan EM, Liu Y. Nat. Commun. 2018; 9: 2998

4 Guo J, Xu Y, Jin S, Chen L, Kaji T, Honsho Y, Addicoat MA, Kim J, Saeki A, Ihee H, Seki S, Irle S, Hiramoto M, Gao J, Jiang D. Nat. Commun. 2013; 4: 2736
5 Kuhn P, Antonietti M, Thomas A. Angew. Chem. Int. Ed. 2008; 47: 3450

6a Pyles DA, Crowe JW, Baldwin LA, McGrier PL. ACS Macro Lett. 2016; 5: 1055
6b Wei PF, Qi MZ, Wang ZP, Ding SY, Yu W, Liu Q, Wang LK, Wang HZ, An WK, Wang W. J. Am. Chem. Soc. 2018; 140: 4623

7 Rao MR, Fang Y, De Feyter S, Perepichka DF. J. Am. Chem. Soc. 2017; 139: 2421
8 Zhang B, Wei M, Mao H, Pei X, Alshmimri SA, Reimer JA, Yaghi OM. J. Am. Chem. Soc. 2018; 140: 12715

9a Grill L, Dyer M, Lafferentz L, Persson M, Peters MV, Hecht S. Nat. Nanotechnol. 2007; 2: 687
9b Lafferentz L, Eberhardt V, Dri C, Africh C, Comelli G, Esch F, Hecht S, Grill L. Nat. Chem. 2012; 4: 215

10 Liu W, Luo X, Bao Y, Liu YP, Ning GH, Abdelwahab I, Li L, Nai CT, Hu ZG, Zhao D, Liu B, Quek SY, Loh KP. Nat. Chem. 2017; 9: 563

11a Zhuang XD, Zhao WX, Zhang F, Cao Y, Liu F, Bia S, Feng XL. Polym. Chem. 2016; 7: 4176
11b Jin E, Asada M, Xu Q, Dalapati S, Addicoat MA, Brady MA, Xu H, Nakamura T, Heine T, Chen Q, Jiang D. Science 2017; 357: 673
11c Jin E, Li J, Geng K, Jiang Q, Xu H, Xu Q, Jiang D. Nat. Commun. 2018; 9: 4143
11d Xu SQ, Wang G, Biswal BP, Addicoat M, Paasch S, Sheng WB, Zhuang XD, Brunner E, Heine T, Berger R, Feng XL. Angew. Chem. Int. Ed. 2019; 58: 849

12a Lyu H, Diercks CS, Zhu C, Yaghi OM. J. Am. Chem. Soc. 2019; 141: 6848
12b Jadhav T, Fang Y, Patterson W, Liu CH, Hamzehpoor E, Perepichka DF. Angew. Chem. Int. Ed. 2019; 58: 13753
12c Wei S, Zhang F, Zhang W, Qiang P, Yu K, Fu X, Wu D, Bi S, Zhang F. J. Am. Chem. Soc. 2019; 141: 14272
12d Bi S, Thiruvengadam P, Wei S, Zhang W, Zhang F, Gao L, Xu J, Wu D, Chen JS, Zhang F. J. Am. Chem. Soc. 2020; 142: 11893

13a Matsuoka R, Sakamoto R, Hoshiko K, Sasaki S, Masunaga H, Nagashio K, Nishihara H. J. Am. Chem. Soc. 2017; 139: 3145
13b Wu SF, Li MC, Phan H, Wang DG, Herng TS, Ding J, Lu ZG, Wu JS. Angew. Chem. Int. Ed. 2018; 57: 8007

14a Zhou D, Tan X, Wu H, Tian L, Li M. Angew. Chem. Int. Ed. 2019; 58: 1376
14b Li C, Wang Y, Zou Y, Zhang X, Dong H, Hu W. Angew. Chem. Int. Ed. 2020; 59: 9403

15a Diaz AF, Castillo JI, Logan JA, Lee WY. J. Electroanal. Chem. 1981; 129: 115
15b Brédas JL, Silbey R, Boudreaux DS, Chance RR. J. Am. Chem. Soc. 1983; 105: 6555

16 Gao J, Jiang D. Chem. Commun. 2016; 52: 1498

17a Ma H, Liu B, Li B, Zhang L, Li YG, Tan HQ, Zang HY, Zhu G. J. Am. Chem. Soc. 2016; 138: 5897
17b Huang N, Wang P, Addicoat MA, Heine T, Jiang D. Angew. Chem. Int. Ed. 2017; 56: 4982

18a Ding H, Li Y, Hu H, Sun Y, Wang J, Wang C, Wang C, Zhang G, Wang B, Xu W, Zhang D. Chemistry 2014; 20: 14614
18b Jin E, Asada M, Xu Q, Dalapati S, Addicoat MA, Brady MA, Xu H, Nakamura T, Heine T, Chen Q, Jiang D. Science 2017; 357: 673
18c Meng Z, Stolz RM, Mirica KA. J. Am. Chem. Soc. 2019; 141: 11929
18d Li H, Chang J, Li S, Guan X, Li D, Li C, Tang L, Xue M, Yan Y, Valtchev V, Qiu S, Fang Q. J. Am. Chem. Soc. 2019; 141: 13324
18e Lakshmi V, Liu CH, Rajeswara Rao M, Chen Y, Fang Y, Dadvand A, Hamzehpoor E, Sakai-Otsuka Y, Stein RS, Perepichka DF. J. Am. Chem. Soc. 2020; 142: 2155

19 Phan H, Herng TS, Wang DG, Li X, Zeng WD, Ding J, Loh KP, Wee AT. S, Wu JS. Chem 2019; 5: 1223
20 Bleaney B. Rev. Mod. Phys. 1953; 25: 161

21a Dong R, Zhang T, Feng X. Chem. Rev. 2018; 118: 6189
21b Liu K, Qi H, Dong R, Shivhare R, Addicoat M, Zhang T, Sahabudeen H, Heine T, Mannsfeld S, Kaiser U, Zheng Z, Feng X. Nat. Chem. 2019; 11: 994
21c Zhang T, Qi H, Liao ZQ, Horev YD, Panes-Ruiz LA, St Petkovf P, Zhang Z, Shivhare R, Zhang P, Liu KJ, Bezugly V, Liu SH. Nat. Commun. 2019; 10: 4225

22 Van Vleck J. The Theory of Electric and Magnetic Susceptibilities. Oxford University Press; Oxford: 1932

Supplementary Material

Supporting Information