A Tris(hydroxymethyl)aminomethane‐Rhodamine Spirolactam Derivative as Dual Channel pH and Water Sensor and Its Application to Bio Imaging

Abstract

A rhodamine spirolactam derivative, R1, having tris(hydroxymethyl)aminomethane moiety as substituent on the spirolactam ring has been synthesized and characterized. R1 shows visual colour change and fluorescence in protic solvents and it is capable of sensing trace amounts of water present in organic solvents. In addition, R1 shows reversible ON-OFF switching in its fluorescence and absorption properties as a function of solution pH. Different from majority of the reported rhodamine spirolactam derivatives, R1 shows

Oxazolidine copper complexes: Synthesis, characterization and superoxide dismutase activity of copper(II) complexes with oxazolidine ligands derived from hydroxyquinoline carboxaldehyde

“…Tris buffer solutions are widely used in molecular and cellular biology for processes such as extraction and purification of proteins, DNA, RNA and nucleic acids, and are still used in clinical practice . On the other hand, there are examples of enzymatic catalytic activity of α‐chymotrypsin complexes used as fluorescent probes, compounds of rhodamine–spirolactam which act as double channels (on–off), anti‐inflammatory activity, photo‐bioreductive compounds, epoxide catalysts, photoluminescence and catalytic transesterification including biodiesel synthesis …”

A sandwich-type zinc complex from a rhodamine dye based ligand: a potential fluorescent chemosensor for acetate in human blood plasma and a molecular logic gate with INHIBIT function

“…This characteristic peak corresponds to the ring opened form of the rhodamine-spirolactam system. 14 On addition of 6.0 equivalents of acetate ions to this solution, a decrease in the fluorescence intensity (quantum yield = 0.009) 21 was observed along with a colour change from intense pink colour to colourless (see Fig. 3).…”

“…The peak due to the tris -OH groups appears as a broad multiplet consisting of two merged triplets suggesting two different environments for -OH groups in the complex. The 13 C NMR showed a shift of the spiro-carbon peak of R from 65.14 14 to 140.34 ppm on complex formation. These spectral data suggest the existence of R in the ring opened spirolactam form R1 in Zn-R1.…”

“…13 Recently we have reported a dual channel sensor, R, based on rhodamine and tris(hydroxymethyl)aminomethane (tris) moieties. 14 R showed high sensitivity towards water and solution pH and it also exhibited potential for bioimaging applications. In continuation of this work, herein we report the synthesis, structural characterization and chemosensing applications of an interesting mono-nuclear zinc complex, Zn-R1, based on R as a ligand.…”

A Novel Mechanism for Chemical Sensing Based on Solvent–Fluorophore–Substrate Interaction: Highly Selective Alcohol and Water Sensor with Large Fluorescence Signal Contrast

“…Various approaches have been explored for selective detection of solvents and solvent vapors, and they can be sorted into four categories based on their sensing mechanism: sorption, − solvatochromism, − chemical reaction, − and dilation. , The sorption-based sensors’ sensory signal is mainly a current or resistance change when chemical adsorption or deactivation of the adsorbed species, such as an ionized oxygen molecule, occurs between two electrodes or under a transistor geometry that is constructed with nanostructured materials, thin films, or composites. − Solvatochromic sensors utilize color and/or fluorescence gradation of the sensory molecules (or metal–organic frameworks), responding to the different solvent polarity. − The sensors based on chemical reaction refer to a system that exhibits color and/or fluorescence alteration by chemical reaction, reduction, oxidation, or metal ion ligation of the sensory molecules upon binding with analytes. − As a dilation-based sensor, the swelling-induced color change of polydiacetylene–polydimethylsiloxane composites and the resistance change in carbon black–polymer composites have been demonstrated. , Even though these sensor systems have demonstrated efficient sensing of target analytes, they often require complicated device fabrication, sophisticated measurement or data processing, and customized material design for specific chemical reactions with analytes.…”