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Synthesis and Optical Properties of alpha,beta-Unsaturated Ketones Bearing a Benzofuran Moiety

  • 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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Metadaten
Author details:Rashid Nazir, Till Thomas MeilingORCiDGND, Piotr J. Cywinski, Daniel T. Gryko
DOI:https://doi.org/10.1002/ajoc.201500242
ISSN:2193-5807
ISSN:2193-5815
Title of parent work (English):Asian journal of organic chemistry : an ACES journal
Publisher:Wiley-VCH
Place of publishing:Weinheim
Publication type:Article
Language:English
Year of first publication:2015
Publication year:2015
Release date:2017/03/27
Tag:aldol reaction; benzofurans; fluorescence; ketones; two-photon absorption
Volume:4
Issue:9
Number of pages:7
First page:929
Last Page:935
Funding institution:National Science Centre of the Republic of Poland [MAESTRO-2012/06A/ST5/00216]; European Community [PITN-GA-2010-264362]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
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