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The Medium-Depending Fluorescence of Quadrupolar Donor-Acceptor-Donor Substituted Distyrylbenzenes with High Two-Photon Absorption Cross-Sections

Published online by Cambridge University Press:  01 February 2011

Heiner Detert
Affiliation:
detert@mail.uni-mainz.de, Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, Duesbergweg 10 - 14, Mainz, Rheinland-Pfalz, 55099, Germany, ++49-6131-3922111
Volker Schmitt
Affiliation:
volkerschmitt@aol.com, Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, Duesbergweg 10 - 14, Mainz, Rheinland-Pfalz, 55099, Germany
Stefan Glang
Affiliation:
stglang@arcor.de, Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, Duesbergweg 10 - 14, Mainz, Rheinland-Pfalz, 55099, Germany
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Abstract

1,4-Distyrylbenzenes with terminal dialkylamino groups and a central 2,5-disubstitution with electron-accepting groups were prepared via twofold Horner-olefination. These chromophores with a quadrupolar donor-acceptor-donor substitution and C2-symmetry absorb in the violet to green region of the visible spectrum exhibit large two-photon-absorption cross-sections when irrdiated in the NIR. Whereas a variation of the solvent polarity only slightly alters the absorption spectra, the fluorescence appears to be highly responsive. Besides a positive solvatochromism, the emission is very sensitive towards protonation. Quenching or appearance of new emitting species depends on the substitution pattern and is controlled by the concentration of the acid.

Type
Research Article
Copyright
Copyright © Materials Research Society 2006

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