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2005•The Journal of Organic ChemistryRequires access

Synthesis and Properties of Novel Fluorescent Switches

Tatiana A. Golovkova, Denis V. Kozlov, Douglas C. Neckers

Open publisher page 230 citations

Abstract

[reaction: see text] Photochromic dithienylethene moieties were covalently attached to fluorescent 4,4-difluoro-8-(4'-iodophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (iodo-BODIPY) via a phenylacetylene linker. UV light induced isomerization of the photochrome results in significant decrease in fluorescence intensity. This fluorescence can be recovered with visible light. Steady-state fluorescence measurements demonstrate that the emission of the dye can be modulated by external light. An intramolecular energy transfer mechanism accounts for the fluorescence quenching in the UV light produced isomers.

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What this paper is about

[reaction: see text] Photochromic dithienylethene moieties were covalently attached to fluorescent 4,4-difluoro-8-(4'-iodophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (iodo-BODIPY) via a phenylacetylene linker. UV light induced isomerization of the photochrome results in significant decrease in fluorescence intensity. This fluorescence can be recovered with visible light. Steady-state fluorescence measurements demonstrate that the emission of the dye can be modulated by external light. An intramolecular energy transfer mechanism accounts for the fluorescence quenching in the UV light produced isomers.

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Available abstract

[reaction: see text] Photochromic dithienylethene moieties were covalently attached to fluorescent 4,4-difluoro-8-(4'-iodophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (iodo-BODIPY) via a phenylacetylene linker. UV light induced isomerization of the photochrome results in significant decrease in fluorescence intensity. This fluorescence can be recovered with visible light. Steady-state fluorescence measurements demonstrate that the emission of the dye can be modulated by external light. An intramolecular energy transfer mechanism accounts for the fluorescence quenching in the UV light produced isomers.

Key concepts: Fluorescence, Photochemistry, Photochromism, Intramolecular force, Fluorescence in the life sciences, Isomerization, BODIPY, Chemistry

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