Download PDF
Synthesis 2011(14): 2334-2339  
DOI: 10.1055/s-0030-1260670
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Bis(4-hydroxythiazoles): Novel Functional and Switchable Fluorophores

Eric Täuschera, Lorena Calderón-Ortiza, Dieter Weiß*a, Rainer Beckert*a, Helmar Görlsb
a Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
Fax: +49(3641)948212; e-Mail: C6bera@uni-jena.de;
b Institute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Lessingstr. 8, 07743 Jena, Germany
Further Information

Publication History

Received 31 March 2011
Publication Date:
16 June 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A series of 2,2′- and 5,5′-bis(4-hydroxythiazoles) was synthesized according to Hantzsch synthesis. Both phenols and their corresponding anions display a strong fluorescence in the visible spectrum, whereas the emission is shifted bathochromically upon deprotonation. This easy switch makes them suitable for widespread applications, mainly in analysis and supramolecular chemistry. Due to their 1,4-diazadiene substructure, the 2,2′-bithiazoles possess prerequisites for the complexation of metals, however, instead of a copper complex, a dimer which constitutes the 5,5′-C-C coupled product was isolated. In addition, tris(thiazoles) could be constructed.

Key words

heterocycles - chromophores - bifunctional compounds - condensation - thiazole

    References

  • 1 Liebscher J. Houben-Weyl   4th ed., Vol. E8b:  Georg Thieme; Stuttgart: 1993.  p.1 ; and references therein
    Google Scholar
  • 2 Kedersky FAJ. Holms JH. Moore JL. Bell RL. Dyer RD. Carter GW. Brooks DW. J. Med. Chem.  1991,  34:  2158 
    CrossrefGoogle Scholar
  • 3 Rzasa RM. Kaller MR. Lia G. Magal E. Nguyen TT. Osslund TD. Powers D. Satora VS. Viswanadhan VN. Wang H.-L. Xiong X. Zhong W. Norman HM. Bioorg. Med. Chem.  2007,  15:  6574 
    CrossrefGoogle Scholar
  • 4a Stippich K. Weiß D. Güther A. Görls H. Beckert R. J. Sulfur Chem.  2009,  30:  109 
    Google Scholar
  • 4b Grummt U.-W. Weiss D. Birckner E. Beckert R. J. Phys. Chem. A  2007,  111:  1104 
    Google Scholar
  • 5 Täuscher E. Weiß D. Beckert R. Görls H. Synthesis  2010,  1603 
    Article in Thieme ConnectGoogle Scholar
  • 6 Täuscher E. Weiß D. Beckert R. Fabian J. Assumpção A. Görls H. Tetrahedron Lett.  2011,  52:  2292 
    CrossrefGoogle Scholar
  • 7a Ma Q. Xu Z. Schroeder BR. Sun W. Wei F. Hashimoto S. Konishi K. Leitheiser CJ. Hecht SM. J. Am. Chem. Soc.  2007,  129:  12439 
    Google Scholar
  • 7b Claussen CA. Long EC. Chem. Rev.  1999,  99:  2797 
    Google Scholar
  • 7c Ninomiya K. Satoh H. Sugiyama T. Shinomiya M. Kuroda R. Chem. Commun.  1996,  1825 
    Google Scholar
  • 7d Glover C. Merritt EA. Bagley MC. Tetrahedron Lett.  2007,  48:  7027 
    Google Scholar
  • 7e Chen H.-J. Wang W.-L. Wang G.-F. Shi L.-P. Gu M. Ren Y.-D. Hou L.-F. He P.-L. Zhu F.-H. Zhong X.-G. Tang W. Zuo J.-P. Nan F.-J. ChemMedChem  2008,  3:  1316 
    Google Scholar
  • 8a Ando S. Murakami R. Nishida J. Tada H. Inoue Y. Tokito S. Yamashita Y. J. Am. Chem. Soc.  2005,  127:  14996 
    Google Scholar
  • 8b Nakagawa T. Atsumi K. Nakashima T. Hasegawa Y. Kawai T. Chem. Lett.  2007,  36:  372 
    Google Scholar
  • 8c MacLean BJ. Pickup PG. J. Mater. Chem.  2001,  11:  1357 
    Google Scholar
  • 9 Mutha SC. Ketcham R. J. Org. Chem.  1969,  34:  2053 
    CrossrefGoogle Scholar
  • 10 Helal A. Lee SH. Kim SH. Kim H.-S. Tetrahedron Lett.  2010,  51:  3531 
    CrossrefGoogle Scholar
  • 11 Tomalia DA. Paige JN. J. Org. Chem.  1973,  38:  3949 
    CrossrefGoogle Scholar
  • 12 Elguero J. Marzin C. Katritzky AR. Linda P. In Advances in Heterocyclic Chemistry   Katritzky AR. Boulton AJ. Academic Press; San Diego: 1976.  p.369 ; and references therein
    Google Scholar
  • 13 Singh-Rachford TN. Nayak A. Muro-Small ML. Goeb S. Therien MJ. Castellano FN. J. Am. Chem. Soc.  2010,  132:  14203 
    CrossrefGoogle Scholar
  • 14 Menzel R. Täuscher E. Weiß D. Beckert R. Görls H. Z. Anorg. Allg. Chem.  2010,  636:  1380 
    CrossrefGoogle Scholar
  • 15 Toda F. Tanaka K. Iwata S. J. Org. Chem.  1989,  54:  3007 
    CrossrefGoogle Scholar
  • 17 Otwinowski W. Minor W. Methods Enzymol.  1997,  276:  307 
    PubMedGoogle Scholar
  • 18 Sheldrick GM. Acta Crystallogr., Sect. A  2008,  46:  112 
    Google Scholar
16

COLLECT, Data Collection Software, Nonius B.V., Netherlands, 1998.

19

Supporting Information Available: Crystallographic data deposited at the Cambridge Crystallographic Data Centre under CCDC-813194 for 4a, and CCDC-813195 for 16 contain the supplementary crystallographic data excluding structure factors; this data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.