A Ratiometric Fluorescent On–Off Zn2+ Chemosensor Based on a Tripropargylamine Pyrene Azide Click Adduct

A Ratiometric Fluorescent On–Off Zn2+ Chemosensor Based on a Tripropargylamine Pyrene Azide Click Adduct

A new, easy-to-prepare and highly selective pyrene-linked tris-triazole amine fluorescent chemosensor has been designed from tripropargylamine and pyrene azide using Cu(I)-catalyzed click chemistry. The fluorescence on–off sensor 1 is highly selective for Zn2+ displaying a ratiometric change in emis...

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Veröffentlicht in:Journal of organic chemistry 2012-10, Vol.77 (20), p.9352-9356
Hauptverfasser: Ingale, Sachin A, Seela, Frank
Format: Artikel
Sprache:eng
Schlagworte:
Analytical chemistry
Azides - chemistry
Catalysis
Chemistry
Click Chemistry
Condensed benzenic and aromatic compounds
Copper - chemistry
Exact sciences and technology
Fluorescence
Fluorescent Dyes - chemistry
General, instrumentation
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Pyrenes - chemistry
Triazoles - chemistry
Zinc - chemistry
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Zusammenfassung:A new, easy-to-prepare and highly selective pyrene-linked tris-triazole amine fluorescent chemosensor has been designed from tripropargylamine and pyrene azide using Cu(I)-catalyzed click chemistry. The fluorescence on–off sensor 1 is highly selective for Zn2+ displaying a ratiometric change in emission. The relative intensity ratio of monomer to excimer fluorescence (M 376/E 465) of the sensor increases 80-fold upon the addition of 10 equiv of Zn2+ ions (with a detection limit of 0.2 μM).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3014319