Synthesis of Quinoline-Based Anion Receptors and Preliminary Anion Binding Studies with Selected Derivatives

Zhanhu Sun; Markus Albrecht; Fangfang Pan; Michel Waringo

doi:10.1055/s-0034-1379605

Synthesis, Table of Contents

Synthesis 2015; 47(06): 861-870
DOI: 10.1055/s-0034-1379605

paper

Synthesis of Quinoline-Based Anion Receptors and Preliminary Anion Binding Studies with Selected Derivatives

Zhanhu Sun

^aInstitut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: Markus.Albrecht@oc.rwth-aachen.de

,

Markus Albrecht*

^aInstitut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: Markus.Albrecht@oc.rwth-aachen.de

,

Fangfang Pan

^bInstitut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

^cDepartment of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9, 40014 Jyväskylä, Finland

,

Michel Waringo

^aInstitut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: Markus.Albrecht@oc.rwth-aachen.de

› Author Affiliations

Abstract

All articles of this category

Abstract

Six quinoline-based anion receptors were designed, prepared, and characterized, among which the crystal structure of an indole derivative was obtained. Selected receptors were tested for the recognition of halide anions in solution and showed some selectivity of chloride over bromide and iodide.

Key words

supramolecular chemistry - receptors - halides - quinolines - indoles

Full Text

References

References
1 Present Address: Z.-H. Sun, Adaptive Supramolecular Nanosystems Group, Institut Européen des Membranes, ENSCM-UMII-UMR-CNRS5635, Place E. Bataillon CC047, 34095 Montpellier Cedex 5, France.
2 Lehn J.-M. Supramolecular Chemistry: Concepts and Perspectives. Wiley; New York: 1995
3 Gale PA. Acc. Chem. Res. 2011; 44: 216
4 Spence GT, Beer PD. Acc. Chem. Res. 2013; 46: 571
5 Sessler JL, Gross DE, Cho WS, Lynch VM, Schmidtchen FP, Bates GW, Light ME, Gale PA. J. Am. Chem. Soc. 2006; 128: 12281

6a Busschaert N, Gale PA. Angew. Chem. Int. Ed. 2013; 52: 1374
6b Gale PA, Hiscock JR, Lalaoui N, Light ME, Wells NJ, Wenzel M. Org. Biomol. Chem. 2012; 10: 5909

7a Hua Y, Flood AH. Chem. Soc. Rev. 2010; 39: 1262
7b Li Y, Flood AH. Angew. Chem. Int. Ed. 2008; 47: 2649

8 Jiang H, Leger JM, Huc I. J. Am. Chem. Soc. 2003; 125: 3448
9 Guichard G, Huc I. Chem. Commun. 2011; 47: 5933
10 Ferrand Y, Chandramouli N, Kendhale AM, Aube C, Kauffmann B, Grelard A, Laguerre M, Dubreuil D, Huc I. J. Am. Chem. Soc. 2012; 134: 11282
11 Gan Q, Ferrand Y, Bao C, Kauffmann B, Grelard A, Jiang H, Huc I. Science 2011; 331: 1172
12 Albrecht M, Witt K, Wegelius E, Rissanen K. Tetrahedron 2000; 56: 591
13 Albrecht M, Triyanti, de Groot M, Bahr M, Weinhold E. Synlett 2005; 2095
14 Albrecht M, Triyanti, Schiffers S, Osetska O, Raabe G, Wieland T, Russo L, Rissanen K. Eur. J. Org. Chem. 2007; 2850
15 Sun Z.-H, Albrecht M, Fröhlich R. Eur. J. Org. Chem. 2013; 3254
16 Sun Z.-H, Pan F.-F, Triyanti, Albrecht M, Raabe G. Eur. J. Org. Chem. 2013; 7922

17a Gale PA, Hiscock JR, Jie CZ, Hursthouse MB, Light ME. Chem. Sci. 2010; 1: 215
17b Hiscock JR, Gale PA, Hynes MJ. Supramol. Chem. 2012; 24: 355

18a Moore SJ, Fisher MG, Yano M, Tong CC, Gale PA. Dalton Trans. 2011; 40: 12017
18b Haynes CJ. E, Moore SJ, Hiscock JR, Marques I, Costa PJ, Félix V, Gale PA. Chem. Sci. 2012; 3: 1436
18c Moore SJ, Wenzel M, Light ME, Morley R, Bradberry SJ, Gómez-Iglesias P, Soto-Cerrato V, Pérez-Tomás R, Gale PA. Chem. Sci. 2012; 3: 2501

19 Yao C, Kraatz HB, Steer RP. Photochem. Photobiol. Sci. 2005; 4: 191

20a Schazmann B, Alhashimy N, Diamond D. J. Am. Chem. Soc. 2006; 128: 8607
20b Xu Z, Singh NJ, Lim J, Pan J, Kim HN, Park S, Kim KS, Yoon J. J. Am. Chem. Soc. 2009; 131: 15528

21 Wang K, Guo D, Jiang B, Liu Y. Sci. China, Ser. B: Chem. 2009; 52: 513
22 Ostergaard ME, Hrdlicka PJ. Chem. Soc. Rev. 2011; 40: 5771
23 Jiang H, Léger J.-M, Dolain C, Guionneau P, Huc I. Tetrahedron 2003; 59: 8365
24 Diedrich CL, Haase D, Saak W, Christoffers J. Eur. J. Org. Chem. 2008; 1811
25 Mateus P, Delgado R, Brandao P, Felix V. J. Org. Chem. 2012; 77: 4611
26 Politzer P, Lane P, Concha MC, Ma Y, Murray JS. J. Mol. Model. 2007; 13: 305

27a Priimagi A, Cavallo G, Metrangolo P, Resnati G. Acc. Chem. Res. 2013; 46: 2686
27b Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G. Angew. Chem. Int. Ed. 2008; 47: 6114

28 Mele A, Metrangolo P, Neukirch H, Pilati T, Resnati G. J. Am. Chem. Soc. 2005; 127: 14972

29a Chudzinski MG, Taylor MS. J. Org. Chem. 2012; 77: 3483
29b Beale TM, Chudzinski MG, Sarwar MG, Taylor MS. Chem. Soc. Rev. 2013; 42: 1667

30 Richardson RD, Zayed JM, Altermann S, Smith D, Wirth T. Angew. Chem. Int. Ed. 2007; 46: 6529
31 Xue L, Liu C, Jiang H. Org. Lett. 2009; 11: 1655
32 Bruker SAINT+, Version 6.45 . Bruker AXS Inc; Madison, Wisconsin: 2003
33 Sheldrick GM. SADABS, Program for Empirical Absorption Correction of Area Detector Data. University of Göttingen; Germany: 2004
34 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
35 CCDC 1013128 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.

Supplementary Material

Supporting Information