Issue 8, 2006

Molecular fluorescent pH-probes based on 8-hydroxyquinoline

Abstract

Three 5,7-π-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.

Graphical abstract: Molecular fluorescent pH-probes based on 8-hydroxyquinoline

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2006
Accepted
15 Feb 2006
First published
14 Mar 2006

Org. Biomol. Chem., 2006,4, 1503-1511

Molecular fluorescent pH-probes based on 8-hydroxyquinoline

S. Kappaun, T. Sović, F. Stelzer, A. Pogantsch, E. Zojer and C. Slugovc, Org. Biomol. Chem., 2006, 4, 1503 DOI: 10.1039/B600912C

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