UV Band Splitting of Chromogenic Azo-Coupled Calix[4]crown upon Cation Complexation

Kim, Jong Yeol; Kim, Guncheol; Kim, Chung Ryul; Lee, Seoung Ho; Lee, Joung Hae; Kim, Jong Seung

doi:10.1021/jo020684o

Cited by 74 publications

(19 citation statements)

References 25 publications

(23 reference statements)

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“…In another investigation, Kim et al 122 reported bifunctional (fluorogenic and chromogenic) calix[4]arene probes 50 and 51 (Figure 11). The (4-nitrophenyl)azo groups of these sensors were introduced as chromogenic moieties 123 to affect the nakedeye detection of F − ions. Probe 50 showed a characteristic fluorescence band at 480 nm originating from the excimer formed by the pyrene moieties.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

et al. 2019

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Calix[n]arenes (n = 4, 5, 6, 8) are "chalicelike" phenol-based macrocycles that are among the most fascinating and highly studied scaffolds in supramolecular chemistry. This stems from the functional and tunable diversity at both their upper and lower rims, their preorganized nonpolar cavities and preorganized ionbinding sites, and their well-defined conformations. Conjugation of calixarene scaffolds with various fluorogenic groups has led to the development of smart fluorescent probes that have been utilized as molecular sensors, in bioimaging, for drug and gene delivery, in self-assembly/aggregation, and as smart materials. The fine-tuning and incorporation of different ligating sites in the calix[4]arene scaffold have produced numerous molecular sensors for cations, anions, and biomolecules. Moreover, the aqueous solubility of p-sulfonatocalix[4]arenes has engendered their potential use in drug/gene delivery and enzymatic assays. In addition, because of their strong optical properties, fluorescent calix[4]arenes have been used to develop smart materials, including gels as well as nonlinear optical, organic light-emitting diode, and multiphoton materials. Finally, significant developments in the utility of fluorescent higher calixarenes have been made for bioapplications. This review critically summarizes the recent advances made in all of these different areas.

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Section: Chemical Reviewsmentioning

confidence: 99%

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

et al. 2019

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“…124). Their conformations were studied by 1 as potential chromogenic sensors [231]. They also wanted to investigate if there was any conformational dependence for the wavelength changes upon complex formation.…”

Section: Fluorescence/luminescencementioning

confidence: 99%

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

Creaven

Donlon

McGinley

2009

Coordination Chemistry Reviews

207

150

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“…However, other specific methods include metal-catalyzed coupling [22][23][24], the oxidation of aromatic amines [25,26], reductive coupling of nitro aromatic compounds [26,27], conversion and reduction of aromatic N-oxides [28][29][30], catalytic coupling and thermal decomposition of aromatic azide compounds [31,32], and the catalytic coupling of aromatic diazonium salts [33][34][35][36]. However, these methods do not meet the requirements of green chemistry owing to the organic solvent and heavy metal ions in the reducing agent or antioxidant.…”

Section: Introductionmentioning

confidence: 99%

New Insight into the Synthesis of Aromatic Azo Compounds Assisted by Surface Plasmon Resonance

Wang

Song

et al. 2016

Plasmonics

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The application of surface plasmon resonance (SPR)-assisted catalysis to synthesize aromatic azo compounds was first reported in 2010. The feasibility of SPRassisted catalytic decomposition of aromatic azo compounds has also been confirmed, both experimentally and theoretically. Compared with traditional chemical synthesis methods, SPR-assisted catalysis has many advantages, such as high efficiency, low energy consumption, and high selectivity. The synthetic route to aromatic azo compounds and the kinetics thereof can be efficiently monitored by Raman spectroscopy. In this way, it has been confirmed that SPR-assisted catalysis occurs on the surface of noble metal nanoparticles (NPs). Mechanistically, the process involves transfer of electrons excited by the incident laser from noble metal NPs to 3 O 2 in air to form 2 O 2 − for the generation of SPR on the surface of the noble metal nanoparticles. The 2 O 2 − can then react with the metal to form metal oxides or hydroxides, which in turn can react with the substrate molecule. The substrate molecule can gain a proton from a proton donor or lose a proton to form a radical, which can react further. This mechanism accounts for the conversion of 4-aminothiophenol (PATP) into 4, 4-dimercaptoazobenzene (DMAB). The metal oxide or hydroxide formed reacts with PATP in an acid-base neutralization process. PATP radicals (PATP · ) are formed by the loss of a proton, and pairing of two PATP · leads to the intermediate product DMHAB. Deprotonation DMHAB then gives the final product DMAB.

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UV Band Splitting of Chromogenic Azo-Coupled Calix[4]crown upon Cation Complexation

Cited by 74 publications

References 25 publications

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials

Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications

New Insight into the Synthesis of Aromatic Azo Compounds Assisted by Surface Plasmon Resonance

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