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A Combined Experimental and Theoretical Approach toward the Development of Optimized Luminescent Carbostyrils

✍ Scribed by Gernot A. Strohmeier; Walter M. F. Fabian; Georg Uray

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
149 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis and photophysical data of new carbostyrils (quinoline‐2(1__H__)‐ones) with the longest hitherto observed absorption‐ and emission wavelengths are described. Introduction of 6‐amino, 7‐MeO, and 4‐(CF~3~) substituents enabled us to rise the absorption and fluorescence maxima up to 414 and 557 nm, respectively. Supported by semi‐empirical and ab initio calculations, the 6,7‐(1,4‐diazine)‐fused carbostyril 23b displayed absorption maxima at up to 440 nm, with quantum yields of up to 0.9 and large Stokes shifts (>100 nm), comparable to the best coumarin chromophores known. The new fluorophore is neither pH‐sensitive between pH 6 and 10 nor susceptible to O~2~ quenching. At pH 3, the emitted light appears greenish‐white, which arises from three different stages of protonation.

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