Synthesis, characterization, photophysics, and anion binding properties of gold(i) acetylide complexes with amide groups

A multicyclophane with a core based on tris(2-aminoethyl)amine (TREN) linked by amide spacers to three fragments of pillar[5]arene was synthesized. The choice of the tris-amide core allowed the multicyclophane to bind to anion guests. The presence of three terminal pillar[5]arene units provides the possibility of effectively binding the colorimetric probe N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine (PhTz). It was established that the multicyclophane complexed PhTz in chloroform with a 1:1 stoichiometry (lgKa = 5.2 ± 0.1), absorbing at 650 nm. The proposed structure of the complex was confirmed by 1H-NMR spectroscopy: the amide group linking the pillar[5]arene to the TREN core forms a hydrogen bond with the PhTz imino-group while the pillararenes surround PhTz. It was established that the PhTz:tris-pillar[5]arene complex could be used as a colorimetric probe for fluoride, acetate, and dihydrogen phosphate anions due to the anion binding with proton donating amide groups which displaced the PhTz probe. Dye displacement resulted in a color change from blue to pink, lowering the absorption band at 650 nm and increasing that at 533 nm.

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The synthesis of two novel neutral receptors and their anion binding properties

Canadian Journal of Chemistry ◽

10.1139/v03-212 ◽

2004 ◽

Vol 82 (3) ◽

pp. 454-460 ◽

Cited By ~ 17

Author(s):

Zhen-Ya Zeng ◽

Yong-Bing He ◽

Lan-Hua Wei ◽

Jin-Long Wu ◽

Yan-Yan Huang ◽

...

Keyword(s):

Hydrogen Bonding ◽

Nmr Spectroscopy ◽

Hydrogen Bonds ◽

Color Change ◽

Anion Recognition ◽

Association Constants ◽

Anion Binding ◽

Binding Properties ◽

Pale Yellow ◽

H Nmr

Two new neutral receptors (1 and 2) containing thiourea and amide groups were synthesized by simple steps in good yields. The binding properties of 1 and 2 with anions were examined by UVvis, fluorescence, and 1H NMR spectroscopy. Receptor 1 had a better AcO: H2PO4 selectivity in comparison with that for receptor 2. The association constants of 1·AcO, 2·AcO, and 2·H2PO4 were higher in comparison with those of other anions (Cl, Br, I, p-NO2PhO, and p-NO2PhOPO32). In particular, a clear color change was observed, from pale yellow to red-brown, upon addition of AcO to the solution of 1 in DMSO. The UVvis and fluorescence data indicate that a 1:1 stoichiometry complex is formed between compound 1 or 2 and anions through hydrogen-bonding interactions.Key words: neutral receptors, anion recognition, synthesis, hydrogen bonds.

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Physical and chemical studies on bacterial superoxide dismutases. Purification and some anion binding properties of the iron-containing protein of Escherichia coli B.

Journal of Biological Chemistry ◽

10.1016/s0021-9258(17)33083-1 ◽

1976 ◽

Vol 251 (18) ◽

pp. 5472-5477 ◽

Cited By ~ 8

Author(s):

T O Slykhouse ◽

J A Fee

Keyword(s):

Escherichia Coli ◽

Anion Binding ◽

Superoxide Dismutases ◽

Binding Properties ◽

Chemical Studies ◽

Physical And Chemical ◽

Escherichia Coli B

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Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Molecules ◽

10.3390/molecules26113394 ◽

2021 ◽

Vol 26 (11) ◽

pp. 3394

Author(s):

Surya B. Adhikari ◽

Anji Chen ◽

Guijun Wang

Keyword(s):

Nucleophilic Substitution ◽

Supramolecular Chemistry ◽

Copper Sulfate ◽

Substitution Reaction ◽

Biological Properties ◽

Anion Binding ◽

Nucleophilic Substitution Reaction ◽

Binding Properties ◽

Intramolecular Nucleophilic Substitution ◽

Leaving Groups

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

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