Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

Jin, Can; Zhang, Man; Deng, Chao; Guan, Yanping; Gong, Junbo; Zhu, Dunru; Pan, Yi; Jiang, Juli; Wang, Leyong

doi:10.1016/j.tetlet.2012.11.117

Cited by 46 publications

(20 citation statements)

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“…During the last decade, squaramide catalysts have become a powerful alternative to the urea/thiourea and guanidine catalysts as multiple hydrogen bond donors in order to design novel bifunctional catalytic scaffolds [ 54 – 55 ]. Hybrid calixarene hosts bearing bis-squaramide moieties at the endo (or lower) and exo (or upper) rims and their recognition properties toward anionic guests have been already reported [ 56 – 57 ]. Therefore, it would be interesting to investigate the application of chiral calixarene-based squaramides in asymmetric catalysis.…”

Section: Reviewmentioning

confidence: 99%

Recent applications of chiral calixarenes in asymmetric catalysis

Durmaz

Halay

Bozkurt

2018

Beilstein J. Org. Chem.

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Section: Reviewmentioning

confidence: 99%

Recent applications of chiral calixarenes in asymmetric catalysis

Durmaz

Halay

Bozkurt

2018

Beilstein J. Org. Chem.

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“…Calixarenes are an important class of macrocyclic compounds, with a wide range of applications in molecular recognition and sensing because of their utility in rigid scaffolds . For example, calix[4]arenes and thiacalix[4]arenes are active molecular platforms used in molecular recognition of cations, anions, and in many biological applications such as enzyme mimics and drug delivery systems …”

Section: Introductionmentioning

confidence: 99%

Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

González‐Hernández

Serrano‐Melgar

Villamil‐Ramos

et al. 2017

Heteroatom Chemistry

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The syntheses, characterization, and inclusion properties of two new trinuclear boron compounds having a calixlike shape are described. Macrocyclic compounds were obtained vía self‐assembly reactions between salicylaldehyde carboxyl derivatives and 3‐aminophenylboronic acid, whereby the formation of three N–B coordination bonds favored the oligomerization process. The products are stable to moisture and have good solubility in organic solvents. The inclusion properties toward primary amines and pyrophosphate were analyzed by titration experiments and monitored by UV‐vis spectroscopy. Association constants around 103‐105 M−1 were determined for both compounds.

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“…The identical changes in 2 's absorption spectra were observed upon the sequential addition of the strong base, tetrabutylammonium (TBA) hydroxide (Figure S16, Supporting Information). This result is explained by an acid–base reaction inducing deprotonation of 2 by AcO − . The deprotonation is visually confirmed by the color change to light yellow after addition of ≈10 equiv of AcO − , whereas very minor color changes are observed for 1 under similar conditions (Figure d–e inset).…”

Section: Resultsmentioning

confidence: 64%

Chemiresistors for the Real‐Time Wireless Detection of Anions

Choi

Yoon

Ray

et al. 2019

Adv Funct Materials

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Reported is an electrical transduction platform for real‐time wireless anion sensing using single‐walled carbon nanotubes (SWCNTs) noncovalently functionalized with squaramide‐based anion binding selectors. Systematically studied are anion‐binding properties and efficiency of the electrical transduction of the functionalized SWCNT composites using the squaramide‐based selectors with two similar electron‐withdrawing groups, 3,5‐bis(trifluoromethyl)benzyl (1) and 3,5‐bis(trifluoromethyl)phenyl (2), which induce hydrogen‐bonding interaction with anions and deprotonation of a squaramide N–H proton upon addition of acetate (AcO−), respectively. Charge transduction occurs with AcO− as a result of charge transfer from the deprotonated selector 2, whereas less sensitive transduction is observed with selector 1 via hydrogen‐bonding interaction. These results provide guidelines to efficiently transduce the chemical interaction between selectors and anions to create resistive transduction with functionalized SWCNTs. Electron‐withdrawing groups adjacent to the squaramide as well as proximate cationic pyridyl groups, enhance the anion binding affinity and also lower the selector's pKa. The chemiresistive sensor arrays are readily integrated with a wireless sensing module and demonstrated real‐time sensing of multiple anions with a smartphone readout.

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Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

Cited by 46 publications

References 50 publications

Recent applications of chiral calixarenes in asymmetric catalysis

Recent applications of chiral calixarenes in asymmetric catalysis

Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

Chemiresistors for the Real‐Time Wireless Detection of Anions

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