Sensing anions on surfaces: tethering triazolium based anion receptors to polymer resins

RSC Advances ◽  
2016 ◽  
Vol 6 (40) ◽  
pp. 33880-33887 ◽  
Author(s):  
S. Byrne ◽  
K. M. Mullen
Keyword(s):  
Chemical Reactivity ◽  
Mas Nmr ◽  
Anion Binding ◽  
Anion Receptors ◽  
Surface Characterisation ◽  
Binding Properties ◽  
Good Surface ◽  
Anion Sensors ◽  
Characterisation Techniques

Herein we report the development of a new series of surface bound triazolium based anion sensors. Differences in the chemical reactivity and anion binding properties were observed; highlighting the need for good surface characterisation techniques such as HR MAS NMR.

Experimental and Theoretical Evidence of the Bidentate Binding Mode of Dichloroacetamido Groups at the Upper Rim of Calix[4]arene Hydrogen-Bonding Anion Receptors

2004 ◽  
Vol 69 (5) ◽  
pp. 1063-1079 ◽  
Author(s):  
Alessandro Casnati ◽  
Francesca Bonetti ◽  
Francesco Sansone ◽  
Franco Ugozzoli ◽  
Rocco Ungaro
Keyword(s):  
Hydrogen Bonding ◽  
Binding Mode ◽  
Association Constants ◽  
Anion Binding ◽  
Anion Receptors ◽  
Binding Properties ◽  
Carboxylate Anions ◽  
Molecular Modeling Studies ◽  
Theoretical Evidence ◽  
Upper Rim

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.

Synthesis and anion binding properties of porphyrins and related compounds

2016 ◽  
Vol 20 (08n11) ◽  
pp. 950-965 ◽  
Author(s):  
Flávio Figueira ◽  
João M.M. Rodrigues ◽  
Andreia A.S. Farinha ◽  
José A.S. Cavaleiro ◽  
João P.C. Tomé
Keyword(s):  
Anion Recognition ◽  
Anion Binding ◽  
Anion Receptors ◽  
Binding Studies ◽  
Binding Properties ◽  
Related Research ◽  
Expanded Porphyrins ◽  
Recent Developments ◽  
Related Compounds

Over the last two decades the preparation of pyrrole-based receptors for anion recognition has attracted considerable attention. In this regard porphyrins, phthalocyanines and expanded porphyrins have been used as strong and selective receptors while the combination of those with different techniques and materials can boost their applicability in different applications as chemosensors and extracting systems. Improvements in the field, including the synthesis of this kind of compounds, can contribute to the development of efficient, cheap, and easy-to-prepare anion receptors. Extensive efforts have been made to improve the affinity and selectivity of these compounds and the continuous expansion of related research makes this chemistry even more promising. In this review, we summarize the most recent developments in anion binding studies while outlining the strategies that may be used to synthesize and functionalize these type of macrocycles.

scholarly journals Carbazole-Based Colorimetric Anion Sensors

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3205
Author(s):  
Krystyna Maslowska-Jarzyna ◽  
Maria L. Korczak ◽  
Jakub A. Wagner ◽  
Michał J. Chmielewski
Keyword(s):  
Hydrogen Bond ◽  
Visible Region ◽  
Building Blocks ◽  
Anion Transport ◽  
Anion Binding ◽  
Anion Receptors ◽  
Binding Studies ◽  
Anion Sensor ◽  
Anion Sensors ◽  
Anion Interaction

Owing to their strong carbazole chromophore and fluorophore, as well as to their powerful and convergent hydrogen bond donors, 1,8-diaminocarbazoles are amongst the most attractive and synthetically versatile building blocks for the construction of anion receptors, sensors, and transporters. Aiming to develop carbazole-based colorimetric anion sensors, herein we describe the synthesis of 1,8-diaminocarbazoles substituted with strongly electron-withdrawing substituents, i.e., 3,6-dicyano and 3,6-dinitro. Both of these precursors were subsequently converted into model diamide receptors. Anion binding studies revealed that the new receptors exhibited significantly enhanced anion affinities, but also significantly increased acidities. We also found that rear substitution of 1,8-diamidocarbazole with two nitro groups shifted its absorption spectrum into the visible region and converted the receptor into a colorimetric anion sensor. The new sensor displayed vivid color and fluorescence changes upon addition of basic anions in wet dimethyl sulfoxide, but it was poorly selective; because of its enhanced acidity, the dominant receptor-anion interaction for most anions was proton transfer and, accordingly, similar changes in color were observed for all basic anions. The highly acidic and strongly binding receptors developed in this study may be applicable in organocatalysis or in pH-switchable anion transport through lipophilic membranes.

Acyclic pyrrole-based anion receptors: design, synthesis, and anion-binding properties

2007 ◽  
Vol 31 (5) ◽  
pp. 646 ◽  
Author(s):  
Jonathan L. Sessler ◽  
Natalie M. Barkey ◽  
G. Dan Pantos ◽  
Vincent M. Lynch
Keyword(s):  
Anion Binding ◽  
Anion Receptors ◽  
Binding Properties ◽  
Design Synthesis

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

Molecules ◽  
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.

scholarly journals Tuning Anion-Binding Properties of 22-Membered Unclosed Cryptands by Structural Modification of the Lariat Arm

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

Anion binding properties for pyrophosphate derived from a 2,6-diamidopyridinedipyrromethane macrocycle

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