Synthesis 2018; 50(02): 303-313
DOI: 10.1055/s-0036-1588581
paper
© Georg Thieme Verlag Stuttgart · New York

Small Molecules as Long-Wavelength Fluorophores: Push-Pull Substituted 4-Alkoxy-1,3-thiazoles

Stefanie H. Habenicht
a   Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany   Email: c6bera@uni-jena.de
,
Philip Rohland
a   Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany   Email: c6bera@uni-jena.de
,
Jeaninne Reichel
a   Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany   Email: c6bera@uni-jena.de
,
Tarita Biver
b   Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Moruzzi 13, 56124 Pisa, Italy
,
Pierpaolo Minei
b   Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Moruzzi 13, 56124 Pisa, Italy
,
Dörthe Jakobi
a   Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany   Email: c6bera@uni-jena.de
,
Andrea Pucci
b   Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Moruzzi 13, 56124 Pisa, Italy
,
Dieter Weiß
a   Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany   Email: c6bera@uni-jena.de
,
Rainer Beckert*
a   Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University, Humboldtstr. 10, 07743 Jena, Germany   Email: c6bera@uni-jena.de
,
Helmar Görls
c   Institute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University, Humboldtstr. 8, 07743 Jena, Germany
› Author Affiliations
Further Information

Publication History

Received: 12 July 2017

Accepted after revision: 07 September 2017

Publication Date:
26 September 2017 (online)


Dedicated to Professor Waldemar Adam on the occasion of his 80th birthday

Abstract

A series of donor-π-acceptor (D-π-A) substituted 4-hydroxythiazoles have been synthesized. Electron-donating groups (4-methoxyphenyl and 4-dimethylaminophenyl) were installed in the 5-position of the thiazole; thiophene/pyridine-bridged acceptors (formyl groups and their Knoevenagel condensation products) were placed in the 2-position. The influence of D-π-A character on the photophysical properties and electronic structure was investigated by means of UV/Vis and fluorescence spectroscopy.

Supporting Information

 
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