Fluorescent Sensor for Rapid Detection of Nucleophile and Convenient Comparison of Nucleophilicity

Abstract

Although nucleophile (Nu) is associated with many important chemical reactions, there are no fluorescence sensors for Nu detection and even for calculation of its nucleophilicity up to the present. In this study, we developed a fluorescent malononitrile-modified perylenediimide (MAPDI) which can selectively and rapidly react with nucleophiles, such as amines, amino acids, and some inorganic anions, and then change its UV–vis absorption and fluorescence emission. Detection limits of MAPDI for different nucleophiles could be calculated to compare their strength of nucleophilicity. Furthermore, it was found that MAPDI could detect reductive inorganic anions. These results suggested that MAPDI might have a great potential in organocatalytic reactions, metal ion-catalyzed reactions, reactions of amines, and other nucleophilic chemical reactions.

A 2-in-1 multi-functional sensor for efficient epinephrine detection based on a cucurbit[7]uril functionalized lanthanide metal–organic framework and its intelligent application in a molecular robot

“…41 To confirm if the mechanism of fluorescence quenching was caused by photoinduced electron transfer (PET), the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy values of the EPI molecules, H 2 bpydc and H 2 bdc were estimated and compared via density functional theory calculations. 42,43 As illustrated in Fig. 5(b and c) we can see that the HOMO and LUMO energy values of H 2 bpydc and H 2 bdc are much lower than those of EPI, which cannot promote a PET process from H 2 bpydc or H 2 bdc to EPI, meaning that a possible PET mechanism can be excluded.…”

Two Chemorobust Cobalt(II) Organic Frameworks as High Sensitivity and Selectivity Sensors for Efficient Detection of 3-Nitrotyrosine Biomarker in Serum

“…In-depth exploration of the sensing mechanism not only helps to understand the nature of recognition at the molecular level but also provides important guidance for the further design and development of more efficient sensors. − Therefore, we have systematically investigated the sensing mechanisms of CoMOFs as sensors for 3-NT from several different perspectives. By comparing the PXRD patterns of recycled CoMOFs samples with the original ones (Figure S21 and Figure S22), the structural-collapse-caused luminescence quenching mechanism can be excluded first .…”

Perylene-Based Fluorescent Nanoprobe for Acid-Enhanced Detection of Formaldehyde in Lysosome

“…Perylene fluorophore has high fluorescence quantum yield and excellent photo/chemical stability, − which has been considered as a suitable fluorophore for bioimaging and detection fields. − Taking advantage of their rigid planar structures, perylene dyes are self-assembled to construct fluorescent nanoparticle that showed enhanced accumulation in lysosome. − For the design of FA probe, homoallylamino derivatives have been reported to react with FA selectively via 2-aza-Cope rearrangement, and this reaction can be promoted in acid environment. , Thus, nanoprobe based on perylene and 2-aza-Cope rearrangement would be promising for FA detection in lysosome with an acidic environment.…”