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Synthesis 2014; 46(01): 126-134
DOI: 10.1055/s-0033-1340048
paper
© Georg Thieme Verlag Stuttgart · New York

From Liquid to Solid-State Fluorescence: Tricyclic Lactones Based on 4-Hydroxy-1,3-thiazoles

Lorena K. Calderón Ortiz
a   Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany    Fax: +49(3641)948212   Email: C6bera@uni-jena.de
,
Hendryk Würfel
a   Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany    Fax: +49(3641)948212   Email: C6bera@uni-jena.de
,
Eric Täuscher
b   Department of Chemistry and Biotechnology, Technical University of Ilmenau, Weimarer Str. 25, 98693 Ilmenau, Germany
,
Dieter Weiß*
a   Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany    Fax: +49(3641)948212   Email: C6bera@uni-jena.de
,
Eckhard Birckner
c   Institute of Physical Chemistry, Friedrich-Schiller-University Jena, Lessingstr. 10, 07743 Jena, Germany
,
Helmar Görls
d   Institute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 9, 07743 Jena, Germany
,
Rainer Beckert*
a   Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany    Fax: +49(3641)948212   Email: C6bera@uni-jena.de
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Publication History

Received: 14 August 2013

Accepted after revision: 30 September 2013

Publication Date:
04 November 2013 (online)

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Dedicated to Prof. Dr. W. Kantlehner, Aalen on the occasion of his 70th birthday

Abstract

This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value.

Key words

heterocycles - chromophores - fused-ring systems - thiazole - fluorescence

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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