Synthesis 2014; 46(08): 1114-1120
DOI: 10.1055/s-0033-1338599
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Extended Chromophores Derived From 5,5-Dimethyloxyluciferin by Barton–Kellogg Methodology

Hendryk Würfel
a   Institut für Organische und Makromolekulare Chemie, Friedrich-Schiller Universität, Humboldtstr. 10, 07743 Jena, Germany   Fax: +49(3641)948212   Email: rainer.beckert@uni-jena.de
,
Luiz Francisco Monteiro Leite Ciscato
b   Universidade Federal do ABC, Centro de Ciências Naturais e Humanas, Rua Santa Adélia, 166 Santo André, SP 09210-170, Brazil
,
Dieter Weiß
a   Institut für Organische und Makromolekulare Chemie, Friedrich-Schiller Universität, Humboldtstr. 10, 07743 Jena, Germany   Fax: +49(3641)948212   Email: rainer.beckert@uni-jena.de
,
Helmar Görls
c   Institut für Anorganische und Analytische Chemie, Friedrich-Schiller Universität, Humboldtstr. 9, 07743 Jena, Germany
,
Rainer Beckert*
a   Institut für Organische und Makromolekulare Chemie, Friedrich-Schiller Universität, Humboldtstr. 10, 07743 Jena, Germany   Fax: +49(3641)948212   Email: rainer.beckert@uni-jena.de
› Author Affiliations
Further Information

Publication History

Received: 18 November 2013

Accepted after revision: 29 January 2014

Publication Date:
25 February 2014 (online)


Abstract

An approach to the synthesis of modified methyl ether-protected dimethyloxyluciferin derivatives is presented, focusing on the enlargement of the π-system. This was achieved by introducing an alkene bridge at the 4-position of the thiazoline moiety to link the two chromophoric substructures. The resulting derivatives show strong absorbing properties over a wide range of the visible spectrum. Also, the fluorescence properties of these novel dimethyl­oxyluciferin derivatives are unique and might lead to new photophysical studies and bioanalytical applications.

 
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