scholarly journals Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1807 ◽  
Author(s):  
Alena Khadieva ◽  
Vladimir Gorbachuk ◽  
Dmitriy Shurpik ◽  
Ivan Stoikov

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.

2014 ◽  
Vol 38 (12) ◽  
pp. 6168-6175 ◽  
Author(s):  
Hua-Yun Shi ◽  
Jie Qi ◽  
Zhen-Ze Zhao ◽  
Wen-Juan Feng ◽  
Yu-Hao Li ◽  
...  

A mononuclear gold(i) acetylide complex with an amide group, 3a, shows a dramatic color change upon addition of F− in DMSO.


2021 ◽  
Vol 8 ◽  
Author(s):  
Utsab Manna ◽  
Bobby Portis ◽  
Tochukwu K. Egboluche ◽  
Muhammad Nafis ◽  
Md. Alamgir Hossain

Two rationally designed 4-nitrophenyl-based molecular clefts functionalized with thiourea (L1) and urea (L2) have been synthesized and studied for a variety of anions by UV-Vis and colorimetric techniques in DMSO. Results from the binding studies suggest that both L1 and L2 bind halides showing the order: fluoride > chloride > bromide > iodide; and oxoanions showing the order: dihydrogen phosphate > hydrogen sulfate > nitrate > perchlorate. Each receptor has been shown to form a 1:1 complex with an anion via hydrogen bonding interactions, displaying distinct color change for fluoride and dihydrogen phosphate in solution. As compared to the urea-based receptor L2, the thiourea-based receptor L1 exhibits stronger affinity for anions due the presence of more acidic thiourea functional groups.


CrystEngComm ◽  
2011 ◽  
Vol 13 (24) ◽  
pp. 7293 ◽  
Author(s):  
Baoliang Lv ◽  
Yao Xu ◽  
Dong Wu ◽  
Yuhan Sun

1972 ◽  
Vol 26 ◽  
pp. 1087-1096 ◽  
Author(s):  
Åke Kvick ◽  
Per-Gunnar Jönsson ◽  
Rune Liminga ◽  
Karin Nilsson ◽  
Wolfgang Nimmich

2021 ◽  
Author(s):  
Xin Wu ◽  
Patrick Wang ◽  
William Lewis ◽  
Yun-Bao Jiang ◽  
Philip Alan Gale

Understanding non-covalent molecular recognition events at biomembrane interfaces is important in biological, medicinal, and materials chemistry research.1 Despite the crucial regulatory roles of anion binding/transport processes at biomembranes, no information is available regarding how strongly anions can bind to naturally occurring or synthetic receptors in lipid bilayer environments compared to their well-established behaviour in solutions.2 To bridge this knowledge gap, we synthesised a flat macrocycle that possesses a record aqueous SO42– affinity among neutral receptors and exploited its unique fluorescence response at interfaces. We show that the determinants of anion binding are extraordinarily different in organic solvents and in lipid bilayers. The high charge density of dihydrogen phosphate and chloride ions prevails in DMSO, however in lipids they fail to bind the macrocycle. Perchlorate and iodide hardly bind in DMSO but show significant affinities for the macrocycle in lipids. Our results demonstrate a surprisingly great advantage of large, charge-diffuse anions to bind to a lipid-embedded synthetic receptor mainly attributed to their higher polarisabilities and deeper penetration into the bilayer, beyond the common knowledge of dehydration energy-governed selectivity. The elucidation of these principles enhances our understanding of biological anion recognition functions in membranes and guides the design of ionophores and molecular machines operating at biomembrane interfaces.


Heterocycles ◽  
2019 ◽  
Vol 98 (4) ◽  
pp. 551
Author(s):  
Quan Gan ◽  
Guoping Li ◽  
Jiulong Li ◽  
Chaocao Lu ◽  
Bu Htan ◽  
...  

2020 ◽  
Vol 11 (29) ◽  
pp. 4749-4759
Author(s):  
Dong Shi ◽  
Wen-Ying Chang ◽  
Xiang-Kui Ren ◽  
Shuang Yang ◽  
Er-Qiang Chen

Side-chain liquid crystalline polynorbornenes based on benzanilide mesogens exhibit rich self-organization behaviours and enhanced mechanical properties owing to the lateral hydrogen bond interaction that can be tuned by the spacer length.


1986 ◽  
Vol 64 (12) ◽  
pp. 2305-2309 ◽  
Author(s):  
Marleen Ruysen ◽  
Thérèse Zeegers-Huyskens

The interaction between ethyl N-(diphenylmethylene)glycinate (DPG) and hydroxy proton donors or pyrrole has been investigated by ir spectrometry. The equilibrium constants, enthalpies, and entropies of complex formation have been determined in carbon tetrachloride solution and compared with the data obtained for the complexes involving N-benzylidene-methylamine and the same proton donors. The ir spectra studied mainly in the νOH, νC=N, νC=O, and νC—O regions suggest that hydrogen bond formation occurs at the N atom of the imino group and at the O atom of the carbonyl group. The results are discussed in terms of the basicity at the two acceptor sites and of the accessibility of the lone pair of electrons. The ir spectra of the solid adduct of DPG with HCl show that protonation takes place on the N atom. The protonated structure is possibly stabilized by an intramolecular hydrogen bond.


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