Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 4, Issue 9, Pages 929-935Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201500242
Keywords
aldol reaction; benzofurans; fluorescence; ketones; two-photon absorption
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Funding
- National Science Centre of the Republic of Poland [MAESTRO-2012/06A/ST5/00216]
- European Community [PITN-GA-2010-264362]
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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)).
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