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)).
| Verfasserangaben: | 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 |
| Titel des übergeordneten Werks (Englisch): | Asian journal of organic chemistry : an ACES journal |
| Verlag: | Wiley-VCH |
| Verlagsort: | Weinheim |
| Publikationstyp: | Wissenschaftlicher Artikel |
| Sprache: | Englisch |
| Jahr der Erstveröffentlichung: | 2015 |
| Erscheinungsjahr: | 2015 |
| Datum der Freischaltung: | 27.03.2017 |
| Freies Schlagwort / Tag: | aldol reaction; benzofurans; fluorescence; ketones; two-photon absorption |
| Band: | 4 |
| Ausgabe: | 9 |
| Seitenanzahl: | 7 |
| Erste Seite: | 929 |
| Letzte Seite: | 935 |
| Fördernde Institution: | National Science Centre of the Republic of Poland [MAESTRO-2012/06A/ST5/00216]; European Community [PITN-GA-2010-264362] |
| Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer Review: | Referiert |
