“…Complexation of lead(II) in acetonitrile solution was connected with large, bathochromic shift resulting in color change from orange to blue. High lead(II) selectivity of these compounds, over other studied metal cations, was also confirmed by experiments on transport through the liquid membranes [ 193 ]. Membrane electrodes doped with 21-membered pyrrole derived crowns 123–125 (Fig.…”
Section: Azo Group(s) In Macrocyclic Compounds Bearing Azole Ringsmentioning
confidence: 80%
“… Fig. 59 Chromogenic crown ethers with pyrrole ( 119 – 125 ) and with imidazole ( 126, 127) heterocyclic residue and with two azo groups in macroring [ 192 , 193 ] …”
Section: Azo Group(s) In Macrocyclic Compounds Bearing Azole Ringsmentioning
confidence: 99%
“…The further studies including 21-membered pyrrole derivatives (compounds 122–125 Fig. 59 ) showed the lead(II) selectivity of this class of compounds [ 193 ]. Complexation of lead(II) in acetonitrile solution was connected with large, bathochromic shift resulting in color change from orange to blue.…”
Section: Azo Group(s) In Macrocyclic Compounds Bearing Azole Ringsmentioning
Azobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for their interesting binding properties. In this article selected macrocyclic compounds bearing azo group(s) are comprehensively described. Here, the relationship between compounds’ structure and their properties (as e.g. ability to guest complexation, supramolecular structure formation, switching and motion) is reviewed.
“…Complexation of lead(II) in acetonitrile solution was connected with large, bathochromic shift resulting in color change from orange to blue. High lead(II) selectivity of these compounds, over other studied metal cations, was also confirmed by experiments on transport through the liquid membranes [ 193 ]. Membrane electrodes doped with 21-membered pyrrole derived crowns 123–125 (Fig.…”
Section: Azo Group(s) In Macrocyclic Compounds Bearing Azole Ringsmentioning
confidence: 80%
“… Fig. 59 Chromogenic crown ethers with pyrrole ( 119 – 125 ) and with imidazole ( 126, 127) heterocyclic residue and with two azo groups in macroring [ 192 , 193 ] …”
Section: Azo Group(s) In Macrocyclic Compounds Bearing Azole Ringsmentioning
confidence: 99%
“…The further studies including 21-membered pyrrole derivatives (compounds 122–125 Fig. 59 ) showed the lead(II) selectivity of this class of compounds [ 193 ]. Complexation of lead(II) in acetonitrile solution was connected with large, bathochromic shift resulting in color change from orange to blue.…”
Section: Azo Group(s) In Macrocyclic Compounds Bearing Azole Ringsmentioning
Azobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for their interesting binding properties. In this article selected macrocyclic compounds bearing azo group(s) are comprehensively described. Here, the relationship between compounds’ structure and their properties (as e.g. ability to guest complexation, supramolecular structure formation, switching and motion) is reviewed.
“…However, the Ag + and Hg 2+ ions show a severe interference with respective selectivity coefficients of 4.54 and 2.2 [13] . The recently reported dibenzyl-tetraoxa-diazacyclooctadecane [14] and pyrrole azocrown ethers [15] are other instances about improving the performance of crown ether ionophores. Although the anti-interference ability over alkali and alkaline-earth metal ions has been greatly enhanced, the transitional metal ions such as Ag +, Cd 2+ and Hg 2+ ions still cause certain interference.…”
“…In this respect, macrocyclic azo compounds, discriminating ions according to their size, serve as a group of molecules of interesting sensing properties and applications [ 21 , 22 ]. Due to presence of an azo moiety, macrocycle-metal cation interaction can be followed by the change of absorption spectra in the visible range of electromagnetic radiation [ 23 , 24 , 25 , 26 , 27 , 28 ]. Until now, a series of chromogenic crown ethers with two azo groups and phenol [ 23 ], pyrrole [ 24 , 25 , 26 , 27 ] or imidazole [ 28 ] residue as a part of macrocycle were synthesized and studied in our group as metal cation complexation agents in solution and as ionophores in membrane ion selective electrodes.…”
Novel 18- and 23-membered diazomacrocycles were obtained with satisfactory yields by diazocoupling of aromatic diamines with pyrrole in reactions carried under high dilution conditions. X-ray structure of macrocycle bearing five carbon atoms linkage was determined and described. Compounds were characterized as chromogenic heavy metal ions receptors. Selective color and spectral response for lead(II) was found in acetonitrile and its mixture with water. Complexation properties of newly obtained macrocycles with a hydrocarbon chain were compared with the properties of their oligoether analogs. The influence of the introduction of hydrocarbon residue as a part of macrocycle on the lead(II) binding was discussed. Selective and sensitive colorimetric probe for lead(II) in aqueous acetonitrile with detection limit 56.1 μg/L was proposed.
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