Download PDF
CC BY 4.0 · Organic Materials 2024; 06(02): 66-70
DOI: 10.1055/s-0044-1787016
Covalent Organic Frameworks (COFs)
Short Communication

Metal-Catalyzed Multi-Component Approach to Quinoline-Linked Covalent Organic Frameworks

Xianghao Han 
a   Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Key Laboratory of Cluster Science, Ministry of Education, Advanced Technology Research Institute (Jinan), Frontiers Science Center for High Energy Material, School of Chemistry and Chemical Engineering, Beijing Institute of Technology. No. 5, South Street, Zhongguancun, Haidian District, Beijing 100081, P. R. of China
,
Shuda Dong 
a   Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Key Laboratory of Cluster Science, Ministry of Education, Advanced Technology Research Institute (Jinan), Frontiers Science Center for High Energy Material, School of Chemistry and Chemical Engineering, Beijing Institute of Technology. No. 5, South Street, Zhongguancun, Haidian District, Beijing 100081, P. R. of China
,
Xiao Feng 
a   Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Key Laboratory of Cluster Science, Ministry of Education, Advanced Technology Research Institute (Jinan), Frontiers Science Center for High Energy Material, School of Chemistry and Chemical Engineering, Beijing Institute of Technology. No. 5, South Street, Zhongguancun, Haidian District, Beijing 100081, P. R. of China
› Author Affiliations
› Further Information
   Permissions and Reprints All articles of this category


Abstract

The development of new reaction chemistry is highly desirable to construct new structural and functional covalent organic frameworks (COFs). Benefiting from the extremely large database of metal-catalyzed reaction database, we herein develop a new synthetic strategy that can generate quinoline-linked COFs via a silver-catalyzed three-component one-pot reaction and achieve functionalization by the simple replacement of alcohols. This metal-catalyzed approach to the construction of robust COF structures characterized by extended π-conjugation holds the potential to pave a novel pathway in the synthesis of COF materials endowed with both heightened stability and functionality.

Key words

covalent organic frameworks - silver-catalyzed - three-component - one-pot - quinoline-linked

Supporting Information



Publication History

Received: 01 February 2024

Accepted after revision: 18 April 2024

Article published online:
17 May 2024

© 2024. The Authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

  • 1 El-Kaderi HM, Hunt JR, Mendoza-Cortes JL, Cote AP, Taylor RE, OʼKeeffe M, Yaghi OM. Science 2007; 316: 268
    CrossrefPubMed
  • 2 Waller PJ, Gandara F, Yaghi OM. Acc. Chem. Res. 2015; 48: 3053
    CrossrefPubMed
  • 3 Liu R, Tan KT, Gong Y, Chen Y, Li Z, Xie S, He T, Lu Z, Yang H, Jiang D. Chem. Soc. Rev. 2021; 50: 120
    CrossrefPubMed
  • 4 Lohse MS, Bein T. Adv. Funct. Mater. 2018; 28: 1705553
    CrossrefPubMed
  • 5 Han SS, Furukawa H, Yaghi OM, Goddard WA. J. Am. Chem. Soc. 2008; 130: 11580
    CrossrefPubMed
  • 6 Huang N, Chen X, Krishna R, Jiang D. Angew. Chem. Int. Ed. 2015; 54: 2986
    CrossrefPubMed
  • 7 Ding S-Y, Gao J, Wang Q, Zhang Y, Song W-G, Su C-Y, Wang W. J. Am. Chem. Soc. 2011; 133: 19816
    CrossrefPubMed
  • 8 Wang X, Han X, Zhang J, Wu X, Liu Y, Cui Y. J. Am. Chem. Soc. 2016; 138: 12332
    CrossrefPubMed
  • 9 Guo J, Jiang D. ACS Cent. Sci. 2020; 6: 869
    CrossrefPubMed
  • 10 Liu J, Wang N, Ma L. Chem. Asian J. 2020; 15: 338
    CrossrefPubMed
  • 11 Jati A, Dey K, Nurhuda M, Addicoat MA, Banerjee R, Maji B. J. Am. Chem. Soc. 2022; 144: 7822
    CrossrefPubMed
  • 12 Vyas VS, Haase F, Stegbauer L, Savasci G, Podjaski F, Ochsenfeld C, Lotsch BV. Nat. Commun. 2015; 6: 8508
    CrossrefPubMed
  • 13 Zhang JL, Yao LY, Yang Y, Liang WB, Yuan R, Xiao DR. Anal. Chem. 2022; 94: 3685
    CrossrefPubMed
  • 14 Yao D, Li C, Wang H, Wen G, Liang A, Jiang Z. Sens. Actuators, B 2020; 319: 128308
    CrossrefPubMed
  • 15 Li Y, Chen M, Han Y, Feng Y, Zhang Z, Zhang B. Chem. Mater. 2020; 32: 2532
    CrossrefPubMed
  • 16 Cui F-Z, Xie J-J, Jiang S-Y, Gan S-X, Ma D-L, Liang R-R, Jiang G-F, Zhao X. Chem. Commun. 2019; 55: 4550
    CrossrefPubMed
  • 17 Li Z, Zhang Y, Xia H, Mu Y, Liu X. Chem. Commun. 2016; 52: 6613
    CrossrefPubMed
  • 18 Fang Q, Wang J, Gu S, Kaspar RB, Zhuang Z, Zheng J, Guo H, Qiu S, Yan Y. J. Am. Chem. Soc. 2015; 137: 8352
    CrossrefPubMed
  • 19 Mitra S, Sasmal HS, Kundu T, Kandambeth S, Illath K, Diaz Diaz D, Banerjee R. J. Am. Chem. Soc. 2017; 139: 4513
    CrossrefPubMed
  • 20 Das S, Sekine T, Mabuchi H, Irie T, Sakai J, Zhao Y, Fang Q, Negishi Y. ACS Appl. Mater. Interfaces 2022; 14: 48045
    CrossrefPubMed
  • 21 Du C, Na W, Shao M, Shang S, Liu Y, Chen J. Chem. Mater. 2023; 35: 1395
    CrossrefPubMed
  • 22 DeBlase CR, Silberstein KE, Thanh-Tam T, Abruna HD, Dichtel WR. J. Am. Chem. Soc. 2013; 135: 16821
    CrossrefPubMed
  • 23 Xu F, Xu H, Chen X, Wu D, Wu Y, Liu H, Gu C, Fu R, Jiang D. Angew. Chem. Int. Ed. 2015; 54: 6814
    CrossrefPubMed
  • 24 Li J, Jing X, Li Q, Li S, Gao X, Feng X, Wang B. Chem. Soc. Rev. 2020; 49: 3565
    CrossrefPubMed
  • 25 Côté AP, Benin AI, Ockwig NW, OʼKeeffe M, Matzger AJ, Yaghi OM. Science 2005; 310: 1166
    CrossrefPubMed
  • 26 Keller N, Bein T. Chem. Soc. Rev. 2021; 50: 1813
    CrossrefPubMed
  • 27 Su Y, Li B, Xu H, Lu C, Wang S, Chen B, Wang Z, Wang W, Otake KI, Kitagawa S, Huang L, Gu C. J. Am. Chem. Soc. 2022; 144: 18218
    CrossrefPubMed
  • 28 Li H, Chavez AD, Li H, Li H, Dichtel WR, Bredas J-L. J. Am. Chem. Soc. 2017; 139: 16310
    CrossrefPubMed
  • 29 Qian C, Qi Q-Y, Jiang G-F, Cui F-Z, Tian Y, Zhao X. J. Am. Chem. Soc. 2017; 139: 6736
    CrossrefPubMed
  • 30 Ma T, Kapustin EA, Yin SX, Liang L, Zhou Z, Niu J, Li LH, Wang Y, Su J, Li J, Wang X, Wang WD, Wang W, Sun J, Yaghi OM. Science 2018; 361: 48
    CrossrefPubMed
  • 31 Vu N, Grunwald M. J. Am. Chem. Soc. 2018; 140: 3306
    CrossrefPubMed
  • 32 Han XH, Gong K, Huang X, Yang JW, Feng X, Xie J, Wang B. Angew. Chem. Int. Ed. 2022; 61: e202202912
    CrossrefPubMed
  • 33 Wang S, Zhang Z, Zhang H, Rajan AG, Xu N, Yang Y, Zeng Y, Liu P, Zhang X, Mao Q, He Y, Zhao J, Li B-G, Strano MS, Wang W-J. Matter 2019; 1: 1592
    CrossrefPubMed
  • 34 Fang Q, Zhuang Z, Gu S, Kaspar RB, Zheng J, Wang J, Qiu S, Yan Y. Nat. Commun. 2014; 5: 4503
    CrossrefPubMed
  • 35 Gu S, Hao R, Chen JJ, Chen X, Liu K, Hussain I, Liu GY, Wang ZQ, Gan QM, Guo H, Li MQ, Zhang KL, Lu ZG. Mater. Chem. Front. 2022; 6: 2545
    CrossrefPubMed
  • 36 Veldhuizen H, Butt SA, van Leuken A, van der Linden B, Rook W, van der Zwaag S, van der Veen MA. ACS Appl. Mater. Interfaces 2023; 15: 29186
    CrossrefPubMed
  • 37 Guan Q, Zhou L-L, Dong Y-B. J. Am. Chem. Soc. 2023; 145: 1475
    CrossrefPubMed
  • 38 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
    CrossrefPubMed
  • 39 Jin E, Li J, Geng K, Jiang Q, Xu H, Xu Q, Jiang D. Nat. Commun. 2018; 9: 4143
    CrossrefPubMed
  • 40 Jadhav T, Fang Y, Patterson W, Liu C-H, Hamzehpoor E, Perepichka DF. Angew. Chem. Int. Ed. 2019; 58: 13753
    CrossrefPubMed
  • 41 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
    CrossrefPubMed
  • 42 Wang Z, Zhang Y, Lin E, Geng S, Wang M, Liu J, Chen Y, Cheng P, Zhang Z. J. Am. Chem. Soc. 2023; 145: 21483
    CrossrefPubMed
  • 43 Zhang B, Wei M, Mao H, Pei X, Alshmimri SA, Reimer JA, Yaghi OM. J. Am. Chem. Soc. 2018; 140: 12715
    CrossrefPubMed
  • 44 Guan X, Li H, Ma Y, Xue M, Fang Q, Yan Y, Valtchev V, Qiu S. Nat. Chem. 2019; 11: 587
    CrossrefPubMed
  • 45 Lu M, Zhang M, Liu CG, Liu J, Shang LJ, Wang M, Chang JN, Li SL, Lan YQ. Angew. Chem. Int. Ed. 2021; 60: 4864
    CrossrefPubMed
  • 46 Liu J, Yang T, Wang Z-P, Wang P-L, Feng J, Ding S-Y, Wang W. J. Am. Chem. Soc. 2020; 142: 20956
    CrossrefPubMed
  • 47 Lei Z, Chen H, Luo C, Rong Y, Hu Y, Jin Y, Long R, Yu K, Zhang W. Nat. Chem. 2022; 14: 1399
    CrossrefPubMed
  • 48 Yang Z, Liu J, Li Y, Zhang G, Xing G, Chen L. Angew. Chem. Int. Ed. 2021; 60: 20754
    CrossrefPubMed
  • 49 Li X-T, Zou J, Wang T-H, Ma H-C, Chen G-J, Dong Y-B. J. Am. Chem. Soc. 2020; 142: 6521
    CrossrefPubMed
  • 50 Grunenberg L, Savasci G, Terban MW, Duppel V, Moudrakovski I, Etter M, Dinnebier RE, Ochsenfeld C, Lotsch BV. J. Am. Chem. Soc. 2021; 143: 3430
    CrossrefPubMed
  • 51 Ren X-R, Bai B, Zhang Q, Hao Q, Guo Y, Wan L-J, Wang D. J. Am. Chem. Soc. 2022; 144: 2488
    CrossrefPubMed
  • 52 Park Y, Kim Y, Chang S. Chem. Rev. 2017; 117: 9247
    CrossrefPubMed
  • 53 Kumar SV, Banerjee S, Punniyamurthy T. Org. Chem. Front. 2020; 7: 1527
    CrossrefPubMed
  • 54 Wang J-C, Kan X, Shang J-Y, Qiao H, Dong Y-B. J. Am. Chem. Soc. 2020; 142: 16915
    CrossrefPubMed
  • 55 Wang Z, Zhang X, Liu W, Sun R, Xu X, Yan Y. Synlett 2016; 27: 1563
    Article in Thieme ConnectPubMed
  • 56 General procedure for the preparation of Q-COF-1: A 10 mL Pyrex tube was charged with TAPB (42.2 mg, 0.12 mmol), DMTP (35.0 mg, 0.18 mmol), and silver trifluoromethanesulfonate (4.6 mg, 0.018 mmol). Then mesitylene (2.0 mL) was added and the mixture was sonicated for 10 min to get a homogeneous dispersion, followed by the addition of trifluoromethanesulfonic acid (3.2 µL, 0.04 mmol) and ethylene glycol (30.1 µL, 0.54 mmol). The mixture was sonicated for 10 min and sealed. The ampoule was warmed to room temperature and then kept at 120 °C without disturbance for 24 h. After being cooled to room temperature, the precipitate was collected through filtration, followed by washing three times with distilled water, EtOH, and THF, respectively. The resulting solid was dried at 120 °C for 6 h under a dynamic vacuum to afford a brown powder (77.7 mg, 98‍% yield).
    PubMed
  • 57 Xu H, Gao J, Jiang D. Nat. Chem. 2015; 7: 905
    CrossrefPubMed
  • 58 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
    CrossrefPubMed