Rational Design of a Chromo- and Fluorogenic Hybrid Chemosensor Material for the Detection of Long-Chain Carboxylates

Citations Over TimeTop 1% of 2004 papers

Abstract

A strategy for the rational design of a new optical sensor material for the selective recognition of long-chain carboxylates in water is presented. The approach relies on the combination of structure-property relationships to single out the optimal molecular sensor unit and the tuning of the sensing characteristics of an inorganic support material. A spacer-substituted 7-urea-phenoxazin-3-one was employed as the signaling moiety and a mesoporous trimethylsilylated UVM-7 (MCM-41 type) material served as the solid support. The sensor material shows the advantageous features of both modules that is absorption and emission in the visible spectral range, a fluorescence red-shift and enhancement upon analyte coordination, and the amplification of noncovalent (binding) and hydrogen-bonding (recognition) interactions in the detection event. Besides these basic results that are related to the design and performance of the sensor material, the paper discusses general aspects of amido-substituted phenoxazinone photophysics and addresses some general features of molecular anion recognition chemistry in aqueous vs nonaqueous media, utilizing steady-state and time-resolved optical as well as NMR spectroscopies. Detailed studies on potentially competing biochemical species and a first access to the schematic model of the response of the sensor material as obtained by a combination of fluorescence lifetime distribution analysis and Langmuir-type fitting of the gross binding constants complement the key issues of the paper.

Related Papers

• → Rational design of the ratiometric fluorescent probes for sulfur dioxide derivatives and the study on the sensing performance of cyano-containing groups(2020)22 cited
• → Rational Design for Complementary Donor–Acceptor Recognition Pairs Using Self‐Complementary Hydrogen Bonds(2015)21 cited
• → Engineering of a synthetic receptor to alter peptide binding selectivity(1995)15 cited
• A Colorimetric and Ratiometric Fluorescent Probes Based on Intramolecular Charge Transfer(2011)
• Ionic liquids containing the urea moiety for recognition of halides and complex anions(2012)