N‐Heterocyclic Carbene Formation Induced Fluorescent and Colorimetric Sensing of Fluoride Using Perimidinium Derivatives

Abstract

In this study, two perimidinium derivatives (1 and 2) were designed, synthesized, and developed as efficient fluorescent and colorimetric chemodosisensors for F(-) in DMSO or more competitive media (DMSO containing 10 % water). In the presence of F(-) , the yellow and non-fluorescent solution of 1/2 became colourless and exhibited strong blue fluorescence. This unique spectroscopic behaviour of 1/2 towards F(-) was attributed to the formation of N-heterocyclic carbene deprotonated by F(-) , which immediately reacted with water to give a colourless and fluorescent carbinol. Interestingly, it was found that this carbinol intermediate was unstable and further underwent a redox disproportionation to generate two other optically changed compounds. All the proposed mechanisms for the sensing process have been carefully confirmed by experiments.

Detection of volatile organic compounds, water in organic solvents, and anions using all-in-one type fluorescent emitters, and their data protection applications

“…17 There is a beneficial effect on dental and skeletal health conferred by trace amounts of F À , 18,19 but intake of F À at concentrations above 2 mg L À1 in drinking water is hazardous and is not recommended according to the World Health Organization (WHO) because it might lead to bone fragility, bone cancer, thyroid disorders, and dental fluorosis. [20][21][22][23] Therefore, the development of a facile, rapid, effective, and low-cost method for the detection and quantification of F À is of great importance in the physiological analysis and environmental monitoring fields.…”

Confinement of a Au–N-heterocyclic carbene in a Pd6L12 metal–organic cage

“…9-11 N-heterocyclic-carbenes (NHCs) are a class of electrondonating ligands, 12 and have been applied in catalyzing various organic transformations. 13,14 Discrete assemblies based on NHC ligands including molecular metallocycles and cages have received increasing attention [15][16][17][18] because they may induce reactivity change, selectivity and product distribution variation. 19,20 However, few molecular cages with well-dened cavities are reported in the literature.…”

A Functional Zn(II) Metallacycle Formed from an N-Heterocyclic Carbene Precursor: A Molecular Sensor for Selective Recognition of Fe3+ and IO4– Ions

“…Over the past few decades, the design and synthesis of receptors for the molecular recognition of ions have drawn tremendous attention from the chemistry community due to their fascinating host–guest interactions that play a decisive role in many areas of chemistry and biology. − In our daily life, ions play a significant role either as an essential requirement for growth or as harmful environmental pollutants. , From this perspective, selective molecular sensing of the ions is still one of the foremost goals for contemporary biologists and chemists. In order to achieve this goal, wide varieties of framework-containing materials, collectively known as coordination polymers (CPs), have widely been used in recent years as fluorescent probes for the selective detection of cations and anions. , Even though N-heterocyclic carbenes (NHCs) have been known for almost five decades and used as the key ligands in the synthesis of a variety of organometallic complexes that are capable of catalyzing various organic transformation reactions, − merely a few reports are available where NHC-based metal complexes were used as fluorescence-based receptors/probes for the recognition of biologically relevant ions: for example, Fe 3+ and periodate (IO 4 – ) ions, the ones reported here. − Neutral iron and its cationic form are some of the prime constituents in physiological processes occurring in the human body as well as in other biological systems. This is because the Fe 3+ ion is the key component of the hemoglobin and is responsible for oxygen metabolism, oxygen uptake, and electron transfer in living organisms. , A deficiency of iron leads to the extremely familiar disease anemia .…”