Download PDF
Synthesis 2023; 55(02): 333-340
DOI: 10.1055/a-1626-5749
paper
Special Issue dedicated to Prof. Alain Krief

Synthesis of Nitrile-Functionalized Polydentate N-Heterocycles as Building Blocks for Covalent Triazine Frameworks

Jonas Everaert
a   SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
,
Maarten Debruyne
a   SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
,
Flore Vanden Bussche
a   SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
b   Department of Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281 (S3), 9000 Ghent, Belgium
,
Kristof Van Hecke
b   Department of Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281 (S3), 9000 Ghent, Belgium
,
Thomas S. A. Heugebaert
a   SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
,
Pascal Van Der Voort
b   Department of Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281 (S3), 9000 Ghent, Belgium
,
Veronique Van Speybroeck
c   Center for Molecular Modeling (CMM), Ghent University, Technologiepark 46, 9052 Zwijnaarde, Belgium
,
Christian V. Stevens  ∗
a   SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
› Author AffiliationsThis work is supported by the Bijzonder Onderzoeksfonds UGent (Research Board of Ghent University; BOF) through a Concerted Research Action (GOA010-17). J.E. acknowledges the Fonds Wetenschappelijk Onderzoek (Research Foundation – Flanders; FWO) for a PhD Fellowship fundamental research (grant 1180421N). K.V.H. thanks the FWO (projects AUGE/11/029 and G099319N) for funding.
› Further Information
    Permissions and Reprints All articles of this category


Dedicated to Prof. Alain Krief on the occasion of his 80th birthday

Abstract

Covalent triazine frameworks (CTFs) based on polydentate ligands are highly promising supports to anchor catalytic metal complexes. The modular nature of CTFs allows to tailor the composition, structure, and function to its specific application. Access to a broad range of chelating building blocks is therefore essential. In this respect, we extended the current available set of CTF building blocks with new nitrile-functionalized N-heterocyclic ligands. This paper presents the synthesis of the six ligands which vary in the extent of the aromatic system and the denticity. The new building blocks may help in a rational design of enhanced support materials in catalysis.

Key words

N-heterocycles - 1,4-diazadiene ligands - 2,2′-bipyridine - 2,2′-biquinoline - 2,6-bis(benzimidazolyl)pyridine - nitrile building blocks - covalent triazine frameworks

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1626-5749.
  • Supporting Information


Publication History

Received: 09 July 2021

Accepted after revision: 31 August 2021

Accepted Manuscript online:
31 August 2021

Article published online:
13 October 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Constable EC. Coord. Chem. Rev. 1989; 93: 205
    Crossref
  • 2 Kaes C, Katz A, Hosseini MW. Chem. Rev. 2000; 100: 3553
    CrossrefPubMed
  • 3 Thompson DW, Ito A, Meyer TJ. Pure Appl. Chem. 2013; 85: 1257
    Crossref
  • 4 Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
    CrossrefPubMed
  • 5 Elgrishi N, Chambers MB, Wang X, Fontecave M. Chem. Soc. Rev. 2017; 46: 761
    CrossrefPubMed
  • 6 Tong L, Thummel RP. Chem. Sci. 2016; 7: 6591
    CrossrefPubMed
  • 7 Yuan Y.-J, Yu Z.-T, Chen D.-Q, Zou Z.-G. Chem. Soc. Rev. 2017; 46: 603
    CrossrefPubMed
  • 8 Gao F, Wang Y, Zhang J, Shi D, Wang M, Humphry-Baker R, Wang P, Zakeeruddin SM, Grätzel M. Chem. Commun. 2008; 2635
    CrossrefPubMed
  • 9 Pashaei B, Karimi S, Shahroosvand H, Abbasi P, Pilkington M, Bartolotta A, Fresta E, Fernandez-Cestau J, Costa RD, Bonaccorso F. Chem. Soc. Rev. 2019; 48: 5033
    CrossrefPubMed
  • 10 Monro S, Colón KL, Yin H, Roque J, Konda P, Gujar S, Thummel RP, Lilge L, Cameron CG, McFarland SA. Chem. Rev. 2019; 119: 797
    CrossrefPubMed
  • 11 Swiegers GF, Malefetse TJ. Chem. Rev. 2000; 100: 3483
    CrossrefPubMed
  • 12 Poynton FE, Bright SA, Blasco S, Williams DC, Kelly JM, Gunnlaugsson T. Chem. Soc. Rev. 2017; 46: 7706
    CrossrefPubMed
  • 13 Marin V, Holder E, Hoogenboom R, Schubert US. Chem. Soc. Rev. 2007; 36: 618
    CrossrefPubMed
  • 14 Newkome GR, He E, Moorefield CN. Chem. Rev. 1999; 99: 1689
    CrossrefPubMed
  • 15 Waki M, Maegawa Y, Hara K, Goto Y, Shirai S, Yamada Y, Mizoshita N, Tani T, Chun W.-J, Muratsugu S, Tada M, Fukuoka A, Inagaki S. J. Am. Chem. Soc. 2014; 136: 4003
    CrossrefPubMed
  • 16 Manna K, Zhang T, Greene FX, Lin W. J. Am. Chem. Soc. 2015; 137: 2665
    CrossrefPubMed
  • 17 Schubert US, Eschbaumer C. Angew. Chem. Int. Ed. 2002; 41: 2892
    CrossrefPubMed
  • 18 Kuhn P, Antonietti M, Thomas A. Angew. Chem. Int. Ed. 2008; 47: 3450
    CrossrefPubMed
  • 19 Liu M, Guo L, Jin S, Tan B. J. Mater. Chem. A 2019; 7: 5153
    Crossref
  • 20 Ren S, Bojdys MJ, Dawson R, Laybourn A, Khimyak YZ, Adams DJ, Cooper AI. Adv. Mater. 2012; 24: 2357
    CrossrefPubMed
  • 21 Yang Z, Chen H, Wang S, Guo W, Wang T, Suo X, Jiang D, Zhu X, Popovs I, Dai S. J. Am. Chem. Soc. 2020; 142: 6856
    CrossrefPubMed
  • 22 Liu M, Huang Q, Wang S, Li Z, Li B, Jin S, Tan B. Angew. Chem. Int. Ed. 2018; 57: 11968
    CrossrefPubMed
  • 23 Hug S, Tauchert ME, Li S, Pachmayr UE, Lotsch BV. J. Mater. Chem. 2012; 22: 13956
    Crossref
  • 24 Tahir N, Muniz-Miranda F, Everaert J, Tack P, Heugebaert TS. A, Leus K, Vincze L, Stevens CV, Van Speybroeck V, Van Der Voort P. J. Catal. 2019; 371: 135
    Crossref
  • 25 Watson G, Gohari Derakhshandeh P, Abednatanzi S, Schmidt J, Leus K, Van Der Voort P. Molecules 2021; 26: 838
    CrossrefPubMed
  • 26 Tahir N, Krishnaraj C, Leus K, Van Der Voort P. Polymers (Basel, Switz.) 2019; 11: 1326
    CrossrefPubMed
  • 27 Abednatanzi S, Gohari Derakhshandeh P, Tack P, Muniz-Miranda F, Liu Y.-Y, Everaert J, Meledina M, Vanden Bussche F, Vincze L, Stevens CV, Van Speybroeck V, Vrielinck H, Callens F, Leus K, Van Der Voort P. Appl. Catal., B 2020; 269: 118769
    Crossref
  • 28 Sigma-Aldrich catalogue, [2,2′-bipyridine]-5,5′-dicarbonitrile (accessed Jul 7, 2021): https://www.sigmaaldrich.com/BE/en/product/ambeedinc/ambh324abb8f?context=bbe
  • 29 Baxter PN. W, Connor JA. J. Organomet. Chem. 1988; 355: 193
    Crossref
  • 30 Janiak C, Deblon S, Wu H.-P. Synth. Commun. 1999; 29: 3341
    Crossref
  • 31 Whittle CP. J. Heterocycl. Chem. 1977; 14: 191
    Crossref
  • 32 Liao L.-Y, Kong X.-R, Duan X.-F. J. Org. Chem. 2014; 79: 777
    CrossrefPubMed
  • 33 Romero FM, Ziessel R. Tetrahedron Lett. 1995; 36: 6471
    Crossref
  • 34 D’Souza DM, Leigh DA, Papmeyer M, Woltering SL. Nat. Protoc. 2012; 7: 2022
    CrossrefPubMed
  • 35 Hayashi E, Shimada N. Yakugaku Zasshi 1977; 97: 123
    CrossrefPubMed
  • 36 Wang H, Pei Y, Bai J, Zhang J, Wu Y, Cui X. RSC Adv. 2014; 4: 26244
    Crossref
  • 37 Jha AK, Jain N. Eur. J. Org. Chem. 2017; 2017: 4765
    Crossref
  • 38 Quinn JR, Zimmerman SC. J. Org. Chem. 2005; 70: 7459
    CrossrefPubMed
  • 39 Garuti L, Roberti M, Malagoli M, Rossi T, Castelli M. Bioorg. Med. Chem. Lett. 2000; 10: 2193
    CrossrefPubMed
  • 40 Veauthier JM, Carlson CN, Collis GE, Kiplinger JL, John KD. Synthesis 2005; 2683
  • 41 Yu P, Morandi B. Angew. Chem. Int. Ed. 2017; 56: 15693
    CrossrefPubMed