Functionalization and Properties of Homooxacalixarenes

Marcos, Paula M.

doi:10.1007/978-3-319-31867-7_17

Cited by 20 publications

(13 citation statements)

References 71 publications

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“…As part of our continuous interest on the host–guest properties of homooxacalixarenes (calixarene analogues in which the CH 2 bridges are partly or completely replaced by CH 2 OCH 2 groups) [ 21 , 22 ], we have reported the anion and ion pair recognition of several (thio)ureido-dihomooxacalix[4]arenes [ 23 , 24 , 25 ], including fluorescent receptors [ 26 , 27 ]. The ion affinity of hexahomotrioxacalix[3]arenes, a very interesting macrocycle formed by an 18-membered ring and having only two basic conformations, has also been investigated [ 28 , 29 , 30 , 31 , 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Miranda

Marcos

Ascenso³

et al. 2022

Molecules

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Fluorescent receptors (4a–4c) based on (thio)ureido-functionalized hexahomotrioxacalix[3]arenes were synthesised and obtained in the partial cone conformation in solution. Naphthyl or pyrenyl fluorogenic units were introduced at the lower rim of the calixarene skeleton via a butyl spacer. The binding of biologically and environmentally relevant anions was studied with NMR, UV–vis absorption, and fluorescence titrations. Fluorescence of the pyrenyl receptor 4c displays both monomer and excimer fluorescence. The thermodynamics of complexation was determined in acetonitrile and was entropy-driven. Computational studies were also performed to bring further insight into the binding process. The data showed that association constants increase with the anion basicity, and AcO−, BzO− and F− were the best bound anions for all receptors. Pyrenylurea 4c is a slightly better receptor than naphthylurea 4a, and both are more efficient than naphthyl thiourea 4b. In addition, ureas 4a and 4c were also tested as ditopic receptors in the recognition of alkylammonium salts.

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Section: Introductionmentioning

confidence: 99%

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Miranda

Marcos

Ascenso³

et al. 2022

Molecules

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“…In the course of our studies on anion binding by disubstituted dihomooxacalix[4]arenes (calix[4]arene analogs in which one CH 2 bridge is replaced by one CH 2 OCH 2 group) (Marcos, 2016) with phenylurea units (Marcos et al, 2014a,b), we were interested in determine the enhancement on the anion binding affinity of the receptors by the introduction of electron-withdrawing groups. Along with this research, the phenylurea derivatives were also evaluated as ditopic receptors (Gattuso et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Ditopic Receptors Based on Dihomooxacalix[4]arenes Bearing Phenylurea Moieties With Electron-Withdrawing Groups for Anions and Organic Ion Pairs

et al. 2019

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Two bidentate dihomooxacalix[4]arene receptors bearing phenylurea moieties substituted with electron-withdrawing groups at the lower rim via a butyl spacer (CF3-Phurea 5b and NO2 Phurea 5c) were obtained in the cone conformation in solution, as shown by NMR. The X-ray crystal structure of 5b is reported. The binding affinity of these receptors toward several relevant anions was investigated by 1H NMR, UV-Vis absorption in different solvents, and fluorescence titrations. Compounds 5b and 5c were also tested as ditopic receptors for organic ion pairs, namely monoamine neurotransmitters and trace amine hydrochlorides by 1H NMR studies. The data showed that both receptors follow the same trend and, in comparison with the unsubstituted phenylurea 5a, they exhibit a significant enhancement on their host-guest properties, owing to the increased acidity of their urea NH protons. NO2-Phurea 5c is the best anion receptor, displaying the strongest complexation for F−, closely followed by the oxoanions BzO−, AcO−, and HSO4-. Concerning ion pair recognition, both ditopic receptors presented an outstanding efficiency for the amine hydrochlorides, mainly 5c, with association constants higher than 109 M−2 in the case of phenylethylamine and tyramine.

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“…Over the past few decades, the development of artificial receptors for ion recognition, complexation, and transportation has proven to be an important topic in both environmental and supramolecular chemistry [ 1 , 2 , 3 , 4 ]. Given their ready availability, and their unique conformational and cavity-containing structures, together with their versatile molecular recognition properties, calixarenes have attracted a great deal of attention during the past several decades, and, indeed, calixarene chemistry has become an indispensable part of supramolecular science [ 5 , 6 , 7 , 8 , 9 ]. Calix[ n ]arenes can provide useful building blocks for host-guest type receptors by appropriate modification.…”

Section: Introductionmentioning

confidence: 99%

A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

Jiang

Ikejiri

et al. 2018

Molecules

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A receptor cone-1 based on a hexahomotrioxacalix[3]arene bearing three pyridyl groups was successfully synthesized, which has a C3-symmetric conformation and is capable of binding alkylammonium and metal ions simultaneously in a cooperative fashion. It can bind alkylammonium ions through the π-cavity formed by three aryl rings. This behaviour is consistent with the cone-in/cone-out conformational rearrangement needed to reorganize the cavity for endo-complexation. As a C3-symmetrical pyridyl-substituted calixarene, receptor cone-1 can also bind an Ag+ ion, and the nitrogen atoms are turned towards the inside of the cavity and interact with Ag+. After complexation of tris(2-pyridylamide) derivative receptor cone-1 with Ag+, the original C3-symmetry was retained and higher complexation selectivity for n-BuNH3+ versus t-BuNH3+ was observed. Thus, it is believed that this receptor will have a role to play in the sensing, detection, and recognition of Ag+ and n-BuNH3+ ions.

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Functionalization and Properties of Homooxacalixarenes

Cited by 20 publications

References 71 publications

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Ditopic Receptors Based on Dihomooxacalix[4]arenes Bearing Phenylurea Moieties With Electron-Withdrawing Groups for Anions and Organic Ion Pairs

A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

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