Anion-binding properties of two calix[4]arene derivatives containing two ferrocene imine or ferrocene amine units at the upper rim

2011 ◽  
Vol 25 (4) ◽  
pp. 317-322 ◽  
Author(s):  
Behrouz Shaabani ◽  
Zohreh Shaghaghi
2004 ◽  
Vol 69 (5) ◽  
pp. 1063-1079 ◽  
Author(s):  
Alessandro Casnati ◽  
Francesca Bonetti ◽  
Francesco Sansone ◽  
Franco Ugozzoli ◽  
Rocco Ungaro

Calix[4]arenes in the 1,3-alternate conformation (1-3) and bearing activated amide groups at the upper rim have been synthesized and their anion binding properties studied and compared with conformationally mobile (4) or cone (Ib) receptors having the same binding groups. Association constants determined in CDCl3 show a stronger complexation for Y-shaped carboxylate anions and a higher efficiency for receptors (Ib and 3) bearing dichloroacetamido moieties as hydrogen bonding donor groups. Molecular modeling studies performed on the cone derivative (Ib) and its 1,3-alternate isomer (10) and ab initio calculations on 4-methoxyaniline derivatives (11-13) used as simplified models, reveal that the α,α-dichloroacetamido moieties bind anions in a bidentate fashion using both the N-H and the CHCl2 as hydrogen bonding donor groups. This explains the higher efficiency in carboxylate binding found for Ib and 3 that incorporate the dichloroacetamido binding unit in their structures.


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3394
Author(s):  
Surya B. Adhikari ◽  
Anji Chen ◽  
Guijun Wang

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.


ACS Omega ◽  
2020 ◽  
Vol 5 (45) ◽  
pp. 29601-29608
Author(s):  
Kajetan Dąbrowa ◽  
Patryk Niedbała ◽  
Marcin Pawlak ◽  
Marcin Lindner ◽  
Wiktor Ignacak ◽  
...  

2021 ◽  
Author(s):  
Rui Yi ◽  
Xing-Li Liu ◽  
Zheng-He Tang ◽  
Chao Huang ◽  
Bi-Xue Zhu ◽  
...  

2008 ◽  
Vol 14 (36) ◽  
pp. 11406-11414 ◽  
Author(s):  
Uk-Il Kim ◽  
Jae-min Suk ◽  
Veluru Ramesh Naidu ◽  
Kyu-Sung Jeong

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