Selective O-functionalization of phenolic α-amino acids with crown ethers bearing cyclophosphazene sub-units

In the present review rotaxanes and pseudorotaxanes with threads containing viologen units are described. First the rotaxanes and pseudorotaxanes in which the crown ether serves as a ring are presented, they are followed by rotaxanes and pseudorotaxanes containing the crown-based cryptand as a ring. For the above interlocked species the synthetic approaches and properties, especially those promising for their use in sensors and switches are shown.

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“…The crown-based lariat ethers are widely used in preparation of membranes and cationconducting channels, [83][84][85][86][87][88] …”

Section: Scheme 13mentioning

confidence: 99%

Rotaxanes and pseudorotaxanes with threads containing viologen units

Deska¹,

Kozłowska²,

Śliwa³

2012

Arkivoc

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“…Complexing compounds are very popular because of the wide application range. They are used among other things: in medicine as a capture and neutralize metal ions compounds [3,4,5], as catalysts in polymerization reactions [6,7,8,9,10,11,12,13], as crown ether complex cation ionic liquids catalysts [14,15,16], as activators [17,18], as protecting groups in organic synthesis [19], as chiral gels utilized as memory-erasing recycle system or logic gates based on the stimuli-responsive gel–sol transition, as chiral selectors to separate amino acid enantiomers in capillary electrophoresis analysis of amino acid enantiomers [20,21,22,23], as effective sensors [24,25,26,27,28,29], as a component of ion-selective membrane electrode [30,31], as extractants for various elements [32,33,34,35,36], and as hydraphiles—synthetic ionophores designed to mimic some properties of protein channels that conduct cations such as sodium [37].…”

Section: Introductionmentioning

confidence: 99%

New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers

Swinarew

Swinarew²,

Gabor

et al. 2019

Polymers

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In today’s analytical trends, there is an ever-increasing importance of polymeric materials for low molecular weight compounds including amines and drugs because they can act as carriers or capture amines or drugs. The use of this type of materials will allow the development of modern materials for the chromatographic column beds and the substrates of selective sensors. Moreover, these kinds of materials could be used as a drug carrier. Therefore, the aim of this study is presenting the synthesis and complexing properties of star-shaped oxiranes as a new sensor for the selective complexation of low molecular weight compounds. Propylene oxide and selected oxirane monomers with carbazolyl in the substituent were selected as the monomers in this case and tetrahydrofuran as its solvent. The obtained polymer structures were characterized using the MALDI-TOF. It was found that in the initiation step potassium hydride deprotonates the monomer molecule and takes also part in the nucleophilic substitution. The resulting polymeric material preferably cross-linked with selected di-oxiranes (1,2,7,8-diepoksyoktan in respect ratio 3:1 according to active center) was then used as a stationary phase in the column and thin layer chromatography for amine separation and identification. Sorption ability of the resulting deposits was determined using a quartz microbalance (QCMB). The study was carried out in stationary mode and flow cells to simulate actual operating phase conditions. Based on changes in electrode vibration frequency, the maximum amount of adsorbed analyte and the best conditions for its sorption were determined.

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“…Macrocyclic derivatives of cyclotriphosphazene and their complexes were found to reveal antitumor activity as well as anti-AIDS activity [37][38][39]. Furthermore, these types of compounds are potentially useful as starting materials for the preparation of 'pH-controlled active ion carriers' in liquid membranes [40].…”

Section: Introductionmentioning

confidence: 99%

“…Molecules 2019, 24, x 3 of 19 cyclotriphosphazene and their complexes were found to reveal antitumor activity as well as anti-AIDS activity [37][38][39]. Furthermore, these types of compounds are potentially useful as starting materials for the preparation of 'pH-controlled active ion carriers' in liquid membranes [40]. This article describes the new P-pivot lariat ether formed by substitution of chlorine atoms in tetrachloro-PNP-macrocycle with the N-benzyl derivative of (S)-prolinamine as side groups (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Mass Spectrometry Reveals Complexing Properties of Modified PNP-Lariat Ether Containing Benzyl Derivative of (S)–Prolinamine

et al. 2019

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In the investigation presented here the synthesis of new lariat ether derivative obtained from the modification of tetrapyrrolidinyl-PNP-crown ether macrocycle is described. The polyheterotopic molecular coreceptor consisted of the replacement of chlorine atoms with an optically active (S)-(1-benzylpyrrolidin-2-yl) methanamine. The structure was confirmed by using elemental analysis, mass spectrometry, and NMR spectroscopy. This work covers results concerning the complexing properties of the new ligand towards Ag + , Cu 2+, Co 2+, Ni 2+ , and Zn 2+ ions. The formation of non-covalent complexes of 1:1 stoichiometry with the Cu 2+, Co 2+, Ni 2+ , and Zn 2+ ions have been confirmed by mass spectrometry. Due to the previous work and application possibilities, a large emphasis was put on the investigation of the complexation ability of lariat ether with silver (I) cation to determine stability constants by direct potentiometric method. In this case, the formation of four different forms of complexes AgL, Ag 2 L, Ag 3 L, and Ag 4 L has been proved. The observed unusual binding through the nitrogen atoms from the exocyclic substituents may provide the structural unit to build a new coordination polymers.Molecules 2020, 25, 136 2 of 19 the preparation of the number of crown ethers, which can be used in various applications such as classical (polymer-supported catalysts PTC, reagents for separation and extraction, etc.) and highly sophisticated (the redox switches for membrane transport, synthetic cation-conducting channels, nucleotide-based molecular boxes and enzyme mimics) [7][8][9][10][11][12]. There are three known main types of lariat ethers: C-pivot lariat ethers [13][14][15], where the side arm is attached to the carbon atom, N-pivot lariat ethers [16][17][18], and finally P-pivot lariat ethers [19,20].The subjects of this research are the P-pivot lariat ether derivatives. The versatile precursors for this type of P-pivot lariat ethers have been obtained by the reaction of hexachlorocyclotriphosphazene with tetraethylene glycol in the presence of sodium hydride (Scheme 1).Molecules 2019, 24, x 2 of 19 various applications such as classical (polymer-supported catalysts PTC, reagents for separation and extraction, etc.) and highly sophisticated (the redox switches for membrane transport, synthetic cation-conducting channels, nucleotide-based molecular boxes and enzyme mimics) [7][8][9][10][11][12]. There are three known main types of lariat ethers: C-pivot lariat ethers [13][14][15], where the side arm is attached to the carbon atom, N-pivot lariat ethers [16][17][18], and finally P-pivot lariat ethers [19,20]. The subjects of this research are the P-pivot lariat ether derivatives. The versatile precursors for this type of P-pivot lariat ethers have been obtained by the reaction of hexachlorocyclotriphosphazene with tetraethylene glycol in the presence of sodium hydride (Scheme 1). Scheme 1. Formation of different types of macrocyclic compounds from hexachlorocyclotriphosphazene substrate. Scheme 1. Formation of dif...

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Selective O-functionalization of phenolic α-amino acids with crown ethers bearing cyclophosphazene sub-units

Cited by 7 publications

References 26 publications

Rotaxanes and pseudorotaxanes with threads containing viologen units

Rotaxanes and pseudorotaxanes with threads containing viologen units

New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers

Mass Spectrometry Reveals Complexing Properties of Modified PNP-Lariat Ether Containing Benzyl Derivative of (S)–Prolinamine

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