Fluorescent Calixarene Scaffolds for NO Detection in Protic Media

Abstract

We present the first fluorescent water‐soluble conjugated calixarene scaffolds that are capable of NO gas detection. Two different scaffolds, one based on a 5,5′‐bicalixarene structure and its isomer bearing two distantly conjugated calixarene moieties, were synthesized. While the fluorescence of both isomers is quenched upon either passing of NO gas or generating it in situ from diethylamine NONOate, the bicalixarene‐based scaffold showed a significantly stronger response. We also present an example of a dye encapsulation strategy to achieve the detection of NO at longer wavelengths than in the parent calixarene host. Finally, a conjugated polymer bearing a 5,5′‐bicalixarene scaffold has also been prepared and demonstrated enhanced sensitivity compared to the monomer due to the molecular wire effect.

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

“…For practical applicability, they further developed watersoluble calix[4]arene probes 95 and 96 for NO detection in protic media (Figure 20). 204 Compared with conjugate 96, probe 95 showed stronger fluorescence emission at 424 nm (λ ex = 395 nm) and high sensitivity for NO in water. In contrast, the complex of 4-(4-dimethylamino)styryl)-N-methylpyridinium dye with probe 96 showed a fluorescent pink color with emission at 590 nm (λ ex = 320 nm, K assoc = 1.0 × 10 5 ) and an efficient response to NO in water.…”

Novel oxadiazole- and triazole-based calixarene derivatives: synthesis and extraction properties

“…Since calixarene skeleton is very versatile and can be converted to many compounds, it has an important role in host-guest chemistry [13][14][15]. For this reason, many extraction and fluorescence studies have been performed with these compounds [16][17][18][19][20]. Especially, in extraction studies, calixarene derivatives seem to be particularly effective in removing carcinogenic azo dyes [21][22][23].…”

Adhesion of Grafted-to Polyelectrolyte Brushes Functionalized with Calix[4]resorcinarene and Deposited as a Monolayer

“…Calixarenes [1][2][3][4][5] are bowl-shaped molecules that can be used to form monolayers on surfaces with controlled orientation due to the hydrophilic nature of the hydroxyls on the upper rim, or via chemical functionalization of the upper or lower rim. [6][7][8][9] This capacity for modification also allows additional functionality to be introduced to a surface or solution.…”

“…[6][7][8][9] This capacity for modification also allows additional functionality to be introduced to a surface or solution. 1,3,6,7,[9][10][11] One potential use of this functionalization is to deliver an adhesive to a surface of interest. In this work, polyelectrolytes, with a view to switchable adhesion applications, [12][13][14][15][16] were delivered to surfaces utilizing the monolayer capacity of calixarene and its hydroxyl rich rim.…”