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)).
Author details: | Rashid Nazir, Till Thomas MeilingORCiDGND, Piotr J. Cywinski, Daniel T. Gryko |
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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 |