Journal
DYES AND PIGMENTS
Volume 93, Issue 1-3, Pages 1428-1433Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2011.10.009
Keywords
Truxene; Phenyleneethynylene; Fluorophore; Sensor; Metalloprotein; Quenching
Funding
- Center of Petroleum, Petrochemicals and Advanced Materials
- National Nanotechnology Center,
- Faculty of Science, Chulalongkorn University [RES-A1B1-5]
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Two new water-soluble fluorophores are synthesized from truxene and ester-substituted aryl acetylenes. The truxene core is decorated by 2-(2'-methoxy)ethoxyethyl groups to enhance the hydrophilicity of these fluorophores as well as to prevent the aggregation by pi-stacking in aqueous media. The conjugated structures are assembled by iodination of the truxene core and subsequent Sonogashira coupling with aryl acetylenes. Upon the hydrolysis of the ester groups, water-soluble fluorophores are obtained in good to excellent yield (30-71% for 3 steps). A photophysical investigation reveals that these compounds exhibit strong fluorescence signals (quantum yield 46-63%) with maximum emission wavelength around 390-400 nm in aqueous phosphate buffer. Preliminary screening on sensing application shows that their fluorescent signals can be selectively quenched by porphyrin-containing metalloproteins. (C) 2011 Elsevier Ltd. All rights reserved.
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