Molecular fluorescent pH-probes based on 8-hydroxyquinoline |
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Authors: | Kappaun Stefan Sović Tanja Stelzer Franz Pogantsch Alexander Zojer Egbert Slugovc Christian |
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Institution: | Institute of Chemistry and Technology of Organic Materials (ICTOS), Graz University of Technology, Stremayrgasse 16, A-8010, Graz, Austria. |
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Abstract: | Three 5,7-pi-extended 8-benzyloxyquinolines, namely 5,7-diphenyl-, 5,7-bis(biphenyl-4-yl)- and 5,7-bis(4-dibenzothiophenyl)-8-benzyloxyquinoline were prepared and investigated as fluorescent pH-probes in nonaqueous solution. Absorption and photoluminescence spectra of the introduced compounds also including the starting material 8-benzyloxy-5,7-dibromoquinoline as well as their N-protonated counterparts were recorded and the results were rationalized by quantum-chemical calculations. A pronounced red shift of the emission occurred upon protonation of the non halogenated derivatives, while the dibromo-derivative is hardly emissive and is virtually not protonated under the conditions used. The diphenyl- and the bis(biphenyl)-derivative especially show promising photoluminescence quantum yields both in the parent and the protonated state making them candidates for the active component in pH sensing applications. |
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