Fluoride Sensing by Catechol‐Based π‐Electron Systems

Abstract

We have developed new catechol-based sensors that can detect fluoride via fluorescence or optical absorption even in the presence of other halides. The level and sensitivity of detection of the sensing molecules is dependent on the chromophore length, which is controlled by the number of thiophene units (one to three) within the chromophore. The sensor with three thiophene units, (E)-2-(2,2'-terthiophen-5-yl)-3-(3,4-dihydroxyphenyl)acrylonitrile, gives the best response to fluoride. By using fluorescence measurements fluoride is detectable over the concentration range 1.7 μM to 200 μM. Importantly, when adsorbed onto a solid support the fluorescent catechol dye can be used to detect the presence of fluoride in aqueous solution.

Positively Charged Lanthanide Complexes with Cyclen-Based Ligands: Synthesis, Solid-State and Solution Structure, and Fluoride Interaction

“…However, fluoride detection in aqueous solution constitutes a difficult task because the sensor has to compete with the strong hydrogen-bonding network formed with water, and a suitable fluoride sensor should be able to detect fluoride in the presence of other competing anions. Among the different systems reported for fluoride recognition, the vast majority use hydrogen-bonding interactions provided by amide, sulfonamide, indole, catechol, (thio)­urea, pyrrole, imidazolium, or positively charged ammonium groups . Recently, fluoride sensing using anion−π interactions has also been reported .…”

Water-soluble dopamine-based polymers for photoacoustic imaging

“…Polydopamine and its derivatives constitute a powerful class of materials of high biological relevance with a multitude of applications. [1][2][3] Synthetic polydopamines are applied as biomimetic (mussel-)adhesives 4 and in metal-coordinating membranes for water purification. 5 The oxidized form of polydopamine, melanin, is ubiquitous in almost all living beings in nature as a granular pigment.…”

The Influence of the Amide Linkage in the FeIII‐Binding Properties of Catechol‐Modified Rosamine Derivatives

“…[3] Amongst the different siderophores,c atechol-based molecules present the highest selectivity andF e III -binding affinity. [6] Our group is particularly interested in the designo fn ew iron chelatorsf or biological and environmental applications, and over recent years we have developed several new bidentate and hexadentate ligandsb yu sing catechol units. [6] Our group is particularly interested in the designo fn ew iron chelatorsf or biological and environmental applications, and over recent years we have developed several new bidentate and hexadentate ligandsb yu sing catechol units.…”

“…Amongst the different siderophores, catechol‐based molecules present the highest selectivity and Fe III ‐binding affinity 4. The properties of these iron‐binding moieties have been explored by synthetic chemists and many catechol conjugates with various functionalized molecules (e.g., drugs or fluorescent probes) have arisen for wide‐ranging applications, including drug delivery, bacterial detection, diagnosis, cancer‐cell recognition,5 and sensing 6…”