Fluorescent probes based on macrocyclic hosts: Construction, mechanism and analytical applications

Jiang, Chenrui; Song, Zhaorui; Yu, Lili; Ye, Sijing; He, Hua

doi:10.1016/j.trac.2020.116086

Cited by 58 publications

(20 citation statements)

References 125 publications

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“…Macrocycles, bearing different functionalities, are often used in many areas, e.g., as drug carriers [ 1 ] or catalysts [ 2 , 3 ]. Macrocyclic compounds are also of interest as a synthetic targets, providing functional systems for sensors, e.g., [ 4 , 5 ], molecular devices and switches c.f. [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Products of Photo- and Thermochemical Rearrangement of 19-Membered di-tert-Butyl-Azoxybenzocrown

et al. 2022

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The preparation and characterization of products of the photochemical and thermochemical rearrangements of 19-membered azoxybenzocrowns with two, bulky, tert-butyl substituents in benzene rings in the para positions to oligooxyethylene fragments (meta positions to azoxy group, i.e., t-Bu-19-Azo-O have been presented. In photochemical rearrangement, two colored typical products were expected, i.e., 19-membered o-hydroxy-m,m′-di-tert-butyl-azobenzocrown (t-Bu-19-o-OH) and 19-membered p-hydroxy-m,m′-di-tert-butyl-azobenzocrown (t-Bu-19-p-OH). In experiments, two colored atypical macrocyclic derivatives, one 6-membered and one 5-membered ring, bearing an aldehyde group (t-Bu-19-al) or intramolecular ester group (t-Bu-20-ester), were obtained. Photochemical rearrangement led to one more macrocyclic product being isolated and identified: a 17-membered colorless compound, without an azo moiety, t-Bu-17-p-OH. The yield of the individual compounds was significantly influenced by the reaction conditions. Thermochemical rearrangement led to t-Bu-20-ester as the main product. The structures of the four crystalline products of the rearrangement—t-Bu-19-o-OH, t-Bu-19-p-OH, t-Bu-20-ester and t-Bu-17-p-OH—were determined by the X-ray method. Structures in solution of atypical derivatives (t-Bu-19-al and t-Bu-20-ester) and t-Bu-19-p-OH were defined using NMR spectroscopy. For the newly obtained hydroxyazobenzocrowns, the azo–phenol⇄quinone–hydrazone tautomeric equilibrium was investigated using spectroscopic methods. Complexation studies of alkali and alkaline earth metal cations were studied using UV-Vis absorption spectroscopy. 1H NMR spectroscopy was additionally used to study the cation recognition of metal cations. Cation binding studies in acetonitrile have shown high selectivity towards calcium over magnesium for t-Bu-19-o-OH.

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Section: Introductionmentioning

confidence: 99%

Products of Photo- and Thermochemical Rearrangement of 19-Membered di-tert-Butyl-Azoxybenzocrown

et al. 2022

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“…ACBs have flexible cavities without closed loop and fluorescent side walls, the fluorescence originates from the benzene and naphthalene side walls of ACBs. The fluorescence enhancement might be due to the increased rigidity of the ACBs, after formation of inclusion complexes, which may prevent intramolecular collisions between the fluorescent side walls and result in nonradiative decay [8] …”

Section: Resultsmentioning

confidence: 99%

“…The fluorescence enhancement might be due to the increased rigidity of the ACBs, after formation of inclusion complexes, which may prevent intramolecular collisions between the fluorescent side walls and result in nonradiative decay. [8] The binding constant (Ks) of WS-23/ACBs inclusion complexes can be obtained by a nonlinear least square's method. Figure 3b ∼ 4b illustrate a typical curve-fitting plot for the titration of ACBs (M1 and M2) with WS-23, which showed the excellent fit between the experimental and calculated data, the 1 : 1 stoichiometry of the WS-23/ACBs inclusion complexes.…”

Section: Spectral Titrationmentioning

confidence: 99%

Synthesis, Characterization and Thermal Controlled Release Of 2‐Isopropyl‐N,2,3‐Trimethylbutyramide with Acyclic Cucurbit[n]urils Inclusion Complexes

Yang

Liao

et al. 2022

ChemistrySelect

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WS‐23 (2 ‐Isopropyl‐ N,2,3 ‐Trimethylbutyramide) is a novel flavor cooling agent, which has been widely used as additive nowadays in food, medicine, cosmetics, daily necessities products, etc. However, its inherent poor solubility and thermal instability seriously limits its further application. Herein, new inclusion systems of WS‐23 with two acyclic cucurbit[n]urils (ACBs) were prepared for the first time, and their binding behaviors in solution and solid states were investigated by means of 1H NMR, 2D ROESY, XRD, FT‐IR SEM, and Fluorescence Spectroscopy. The data reveal that the stoichiometric ratio of the inclusion complex is 1 : 1, the solubility of WS‐23 can be enhanced by ca. 19.39 ‐ 31.72 folds. Besides, the heat‐controlled release properties of WS‐23 from the solid inclusion complexes were also investigated by TGA and 1H‐NMR, and its thermal stability in two inclusion complexes are both greatly improved. WS‐23 /M1(M2) exhibited a longer retention time in tobacco products and effectively improve the sensory quality. In brief, our work provides theoretical data and technical guidance for the development and application of water soluble WS‐23 with controlled heat release, which might further application of WS‐23 in the field of commercial industry.

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“…1), namely cyclodextrins, 1 cucurbiturils, 2 calixarenes, 3 pillarenes, 4 resorcinarenes, 5 and their bowlshaped structures "cavitands", 6,7 is of great interest. 8 Such supramolecular-photochemical combination can be considered as a key-step process for the development of new type of fluorescent chemosensors, not only for chemistry but also for other disciplines such as medicine, biology, and environmental science. [9][10][11][12] In particular, environmental contamination by heavy metals and pesticides is a major concern as their cumulative effects pose significant risks to human health.…”

Section: Introductionmentioning

confidence: 99%

“…1) have been widely used as fruitful platforms giving rise to ionophores for neutral and ionic guest species. 8,24,25 Their unique structural characteristics including rigid cores that manipulate their cavity size upon varying type and/or number of the covalent spacers between the adjacent phenols, 26,27 the relative ease of chemical modification on their backbones without breaking the structural integrity of the inner cavity, 27 along with the inherit spatial directionality acquired by their upper rims 25 offer unparalleled opportunities for synthetic chemists to explore their utility as molecular platforms for attaching multiple photoactive sites, such as boron-dipyrromethene (BODIPY), onto their backbone structures for the synthesis of innovative chemosensing-based macrocyclic systems.…”

Section: Introductionmentioning

confidence: 99%

A highly sensitive “ON–OFF–ON” dual optical sensor for the detection of Cu(ii) ion and triazole pesticides based on novel BODIPY-substituted cavitand

et al. 2021

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Fluorescent probes based on macrocyclic hosts: Construction, mechanism and analytical applications

Cited by 58 publications

References 125 publications

Products of Photo- and Thermochemical Rearrangement of 19-Membered di-tert-Butyl-Azoxybenzocrown

Products of Photo- and Thermochemical Rearrangement of 19-Membered di-tert-Butyl-Azoxybenzocrown

Synthesis, Characterization and Thermal Controlled Release Of 2‐Isopropyl‐N,2,3‐Trimethylbutyramide with Acyclic Cucurbit[n]urils Inclusion Complexes

A highly sensitive “ON–OFF–ON” dual optical sensor for the detection of Cu(ii) ion and triazole pesticides based on novel BODIPY-substituted cavitand

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