Enantiodifferentiation of carboxylates by chiral building blocks for abiotic anion receptors

Author(s):  
Alexander Gleich ◽  
Franz P. Schmidtchen ◽  
Patrizia Mikulcik ◽  
Gerhard Müller
1995 ◽  
Vol 60 (4) ◽  
pp. 1039-1043 ◽  
Author(s):  
Wolfgang Peschke ◽  
Petra Schiessl ◽  
Franz P. Schmidtchen ◽  
Peter Bissinger ◽  
Annette Schier

2007 ◽  
Vol 79 (6) ◽  
pp. 1087-1096 ◽  
Author(s):  
Michał J. Chmielewski ◽  
Tomasz Zieliński ◽  
Janusz Jurczak

Understanding of structure-affinity relationships is crucial for rational receptor design, however, such studies for anion receptors are still limited. Therefore, we investigated this issue in the case of amide-based macrocyclic receptors derived from aromatic diacids (i.e., isophthalic and dipicolinic). Using these model compounds, we examined the macrocyclic effect, the influence of intramolecular hydrogen bonds, and the correlation between the ring size and anion affinity. We found that in contrast to what was known for acyclic diamides, macrocyclic isophthalamide receptors bind anions more weakly than their dipicolinic analogs. Comprehensive structural studies revealed that such behavior is due to intramolecular hydrogen bonds present in isophthalamide receptors. Furthermore, we demonstrated how this obstacle can be overcome by the preparation of a hybrid macrocycle based on both building blocks.


Author(s):  
Ryota Sato ◽  
Hajime Okajima ◽  
Shinya Sugiura ◽  
Yohei Haketa ◽  
Yusuke Kinoshita ◽  
...  

Anion-responsive photofunctional materials have been extensively studied because anions are important for biotic activity and constitute the building blocks of elegant supramolecular architectures. A number of fluorescent anion receptors that...


2011 ◽  
Vol 83 (8) ◽  
pp. 1543-1554 ◽  
Author(s):  
Janusz Jurczak ◽  
Michał J. Chmielewski ◽  
Paweł Dydio ◽  
Dawid Lichosyt ◽  
Filip Ulatowski ◽  
...  

Neutral anion receptors working in highly demanding solvents are new materials being sought. Benzopyrroles are more acidic than amides and pyrrole itself, and are promising building blocks in the design of host compounds. A whole series of receptors based upon benzopyrroles were synthesized and evaluated. They include carbazole, dipyrrolonaph-thalene, and 7-aminoindole-based hosts. Most of them demonstrate moderate binding affinities in dimethyl sulfoxide (DMSO) and have good selectivity toward tetrahedral oxyanions. Recently, a group of receptors utilizing 7-aminoindole and urea moieties proved to work in a very competitive solvent—methanol.


2007 ◽  
pp. 1136-1138 ◽  
Author(s):  
Hiromitsu Maeda ◽  
Yoshihiro Ito ◽  
Yukio Kusunose ◽  
Takashi Nakanishi

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3205
Author(s):  
Krystyna Maslowska-Jarzyna ◽  
Maria L. Korczak ◽  
Jakub A. Wagner ◽  
Michał J. Chmielewski

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.


2011 ◽  
Vol 133 (23) ◽  
pp. 8896-8899 ◽  
Author(s):  
Hiromitsu Maeda ◽  
Kazumasa Naritani ◽  
Yoshihito Honsho ◽  
Shu Seki

1997 ◽  
Vol 161 ◽  
pp. 23-47 ◽  
Author(s):  
Louis J. Allamandola ◽  
Max P. Bernstein ◽  
Scott A. Sandford

AbstractInfrared observations, combined with realistic laboratory simulations, have revolutionized our understanding of interstellar ice and dust, the building blocks of comets. Since comets are thought to be a major source of the volatiles on the primative earth, their organic inventory is of central importance to questions concerning the origin of life. Ices in molecular clouds contain the very simple molecules H2O, CH3OH, CO, CO2, CH4, H2, and probably some NH3and H2CO, as well as more complex species including nitriles, ketones, and esters. The evidence for these, as well as carbonrich materials such as polycyclic aromatic hydrocarbons (PAHs), microdiamonds, and amorphous carbon is briefly reviewed. This is followed by a detailed summary of interstellar/precometary ice photochemical evolution based on laboratory studies of realistic polar ice analogs. Ultraviolet photolysis of these ices produces H2, H2CO, CO2, CO, CH4, HCO, and the moderately complex organic molecules: CH3CH2OH (ethanol), HC(= O)NH2(formamide), CH3C(= O)NH2(acetamide), R-CN (nitriles), and hexamethylenetetramine (HMT, C6H12N4), as well as more complex species including polyoxymethylene and related species (POMs), amides, and ketones. The ready formation of these organic species from simple starting mixtures, the ice chemistry that ensues when these ices are mildly warmed, plus the observation that the more complex refractory photoproducts show lipid-like behavior and readily self organize into droplets upon exposure to liquid water suggest that comets may have played an important role in the origin of life.


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