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Synthesis and optical properties of alpha,beta-unsaturated ketones bearing a benzofuran moiety

 
: Nazir, R.; Meiling, T.T.; Cywiński, P.J.; Gryko, D.T.

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Asian journal of organic chemistry 4 (2015), Nr.9, S.929-935
ISSN: 2193-5807
European Commission EC
FP7-PEOPLE; 264362; TOPBIO
Englisch
Zeitschriftenaufsatz
Fraunhofer IAP ()

Abstract
Five pi-expanded alpha,beta-unsaturated ketones have been prepared from a strongly electron-rich benzofuran derivative via Knoevenagel reaction and aldol condensation. The incorporation of two 6-didodecylaminobenzofuran-2-yl groups at the periphery of D-pi-A and D-pi-A-pi-D molecules resulted in dyes with excellent solubility in the majority of organic solvents. In contrast to the majority of alpha,beta-unsaturated ketones, these dyes emit relatively strongly in the red region with a fluorescence quantum yield up to 40%. They also display strong solvatofluorochromism with emission shifting from 570 nm in toluene to 670 nm in CHCl3. Depending on the chemical structure, they two-photon cross-sections (sigma(2)) are up to 1700 GM (1 GM=10(50) cm(4)s photon(-1)).

: http://publica.fraunhofer.de/dokumente/N-369527.html