Synlett 2013; 24(15): 1899-1909
DOI: 10.1055/s-0033-1339691
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© Georg Thieme Verlag Stuttgart · New York

Adventures of an Occasional Click Chemist

Uwe H. F. Bunz*
a   Ruprecht-Karls-Universität Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: +49(6221)548401   eMail: uwe.bunz@oci.uni-heidelberg.de
b   Ruprecht-Karls-Universität Heidelberg, Centre of Advanced Materials, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany
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Publikationsverlauf

Received: 15. Mai 2013

Accepted: 10. Juni 2013

Publikationsdatum:
13. August 2013 (online)


Dedicated to Günter Szeimies

Abstract

In this account, I describe my and my group’s adventures in the field of 1,3-dipolar cycloaddition reactions of alkynes to organic azides. Three different topics are treated: post-functionalization and crosslinking of polymers of the poly(phenylene ethynylene) type, the synthesis of conjugated heterocyclic polymers by clicking aromatic diazides to aromatic diynes, and the synthesis of fluorophore dyes that bind to metal cations. In the last case, as a result of the presence of a binding pocket created by a triazole nitrogen and the nitrogen of a neighboring heterocycle (pyridine, chalcodiazole, or phenazine), the binding event leads to specific changes in the absorption and emission spectra of the complex. This account is limited exclusively to experiments performed by our group, as the topic of 1,3-dipolar cycloadditions of azides to alkynes has already been the subject of many comprehensive reviews and accounts.

1 Introduction

2 Polymeric Clicks

3 Metallosensors by Click Chemistry

4 Outlook and Conclusion

 
  • References

    • 1a Huisgen R, Szeimies G, Möbius L. Chem. Ber. 1967; 100: 2494
    • 1b Huisgen R. Pure Appl. Chem. 1989; 61: 613
    • 2a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. 2002; 41: 2596
    • 2b Kolb HC, Finn MG, Sharpless KB. Angew. Chem. 2001; 40: 2004
    • 2c Huisgen R. Angew. Chem. Int. Ed. Engl. 1963; 2: 565
    • 3a Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
    • 3b Binder WH, Sachsenhofer R. Macromol. Rapid Commun. 2007; 28: 15
    • 3c Meldal M, Tornoe CW. Chem. Rev. 2008; 108: 2952
    • 3d Lutz JF. Angew. Chem. 2007; 46: 1018
    • 3e Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. 2005; 44: 5188
    • 4a Helms B, Mynar JL, Hawker CJ, Fréchet JM. J. J. Am. Chem. Soc. 2004; 126: 15020
    • 4b Kolb HC, Sharpless KB. Drug Discovery Today 2003; 8: 1128
    • 4c Díaz DD, Punna S, Holzer P, McPherson AK, Sharpless KB, Fokin VV, Finn MG. J. Polym. Sci., Part A: Polym. Chem. 2004; 42: 4392
    • 5a Berg R, Straub J, Schreiner E, Mader S, Rominger F, Straub BF. Adv. Synth. Catal. 2012; 354: 3445
    • 5b Chan TR, Hilgraf R, Sharpless KB, Fokin VV. Org. Lett. 2004; 6: 2853
  • 6 Erdogan B, Song LL, Wilson JN, Park JO, Srinivasarao M, Bunz UH. F. J. Am. Chem. Soc. 2004; 126: 3678
  • 7 Bunz UH. F. Adv. Mater. (Weinheim, Ger.) 2006; 18: 973
  • 8 Englert BC, Bakbak S, Bunz UH. F. Macromolecules 2005; 38: 5868
  • 9 Phillips RL, Kim I.-B, Tolbert LM, Bunz UH. F. J. Am. Chem. Soc. 2008; 130: 6952
  • 10 Kim IB, Erdogan B, Wilson JN, Bunz UH. F. Chem. Eur. J. 2004; 10: 6247
  • 11 Phillips RL, Kim I.-B, Carson BE, Tidbeck B, Bai Y, Lowary TL, Tolbert LM, Bunz UH. F. Macromolecules 2008; 41: 7316
    • 12a Roy R. Trends Glycosci. Glycotechnol. 2003; 15: 291
    • 12b Chabre YM, Roy R. Adv. Carbohydr. Chem. Biochem. 2010; 63: 165
  • 13 Mammen M, Choi SK, Whitesides GM. Angew. Chem. Int. Ed. 1998; 37: 2755
  • 14 Bakbak S, Leech PJ, Carson BE, Saxena S, King WP, Bunz UH. F. Macromolecules 2006; 39: 6793
  • 15 van Steenis DJ. V. C, David OR. P, van Strijdonck GP. F, van Maarseveen JH, Reek JN. H. Chem. Commun. 2005; 4333
  • 16 Bunz UH. F. Chem. Rev. 2000; 100: 1605
  • 17 Bunz UH. F, Mäker D, Porz M. Macromol. Rapid Commun. 2012; 33: 886
    • 18a Hauck M, Schönhaber J, Zucchero AJ, Hardcastle KI, Müller TJ. J, Bunz UH. F. J. Org. Chem. 2007; 72: 6714
    • 18b Zucchero AJ, McGrier PL, Bunz UH. F. Acc. Chem. Res. 2010; 43: 397
  • 19 For a review on triazole and tetrazole compounds as ligands, see: Aromí G, Barrios LA, Roubeau O, Gamez P. Coord. Chem. Rev. 2011; 255: 485
  • 20 Bryant JJ, Bunz UH. F. Chem. Asian J. 2013; 8: 1354
  • 21 Schweinfurth D, Hardcastle KI, Bunz UH. F. Chem. Commun. 2008; 2203
  • 22 Brombosz SM, Zucchero AJ, Phillips RL, Vazquez D, Wilson A, Bunz UH. F. Org. Lett. 2007; 9: 4519
  • 23 Brombosz SM, Appleton AL, Zappas AJ. II, Bunz UH. F. Chem. Commun. 2010; 1419
  • 24 Appleton AL, Miao S, Brombosz SM, Berger NJ, Barlow S, Marder SR, Lawrence BM, Hardcastle KI, Bunz UH. F. Org. Lett. 2009; 11: 5222
  • 25 Bryant JJ, Lindner BD, Bunz UH. F. J. Org. Chem. 2013; 78: 1038
  • 26 Coombs BA, Lindner BD, Edkins RM, Rominger F, Beeby A, Bunz UH. F. New J. Chem. 2012; 36: 550
    • 27a Kumpf J, Bunz UH. F. Chem. Eur. J. 2012; 18: 8921
    • 27b Bunz UH. F. Macromol. Rapid Commun. 2009; 30: 772
  • 28 Tolosa J, Bryant JJ, Solntsev KM, Brödner K, Tolbert LM, Bunz UH. F. Chem. Eur. J. 2011; 17: 13726
  • 29 Phillips RL, Miranda OR, Mortenson DE, Subramani C, Rotello VM, Bunz UH. F. Soft Matter 2009; 5: 607
  • 30 Bryant JJ, Zhang Y, Lindner BD, Davey EA, Appleton AL, Qian X, Bunz UH. F. J. Org. Chem. 2012; 77: 7479
    • 31a Gordon CG, Mackey JL, Jewett JC, Sletten EM, Houk KN, Bertozzi CR. J. Am. Chem. Soc. 2012; 134: 9199
    • 31b Sletten EM, Nakamura H, Jewett JC, Bertozzi CR. J. Am. Chem. Soc. 2010; 132: 11799
    • 31c Agard NJ, Prescher JA, Bertozzi CR. J. Am. Chem. Soc. 2004; 126: 15046