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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Author:Rashid Nazir, Till Thomas MeilingORCiDGND, Piotr J. Cywinski, Daniel T. Gryko
ISSN:2193-5807 (print)
ISSN:2193-5815 (online)
Parent Title (English):Asian journal of organic chemistry : an ACES journal
Place of publication:Weinheim
Document Type:Article
Year of first Publication:2015
Year of Completion:2015
Release Date:2017/03/27
Tag:aldol reaction; benzofurans; fluorescence; ketones; two-photon absorption
First Page:929
Last Page:935
Funder: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