Synthesis of novel diazacyclam copper(II) complexes by template reaction involving sulphonamides as locking fragments

Licchelli, Maurizio; Milani, Michele; Pizzo, Sergio; Poggi, Antonio; Sacchi, Donatella; Boiocchi, Massimo

doi:10.1016/j.ica.2011.12.001

Cited by 4 publications

(4 citation statements)

References 52 publications

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“…All the investigated compounds are expected to display a strong stability in water, as previously observed for other azacyclam complexes, and more in general, for metal complexes of 14-membered macrocyclic ligands displaying a 5-6-5-6 sequence of chelate rings [ 86 , 89 , 90 ].…”

Section: Resultssupporting

confidence: 58%

“…The absorption spectra of the investigated azacyclam complexes taken in the 200–400 nm (about 10 −5 M) as well as in the 400–800 nm range (about 10 −3 M) are reported in Figures S1–S3 . The weak band observed in the visible region results from an envelope of the three possible d–d transitions (xz, yz→x 2 -y 2 , z 2 →x 2 -y 2 , and xy→x 2 -y 2 ) in the square-planar copper(II)-tetramine chromophore [ 85 , 86 ]. Spectral data of the investigated complexes as well as of [Cu(2.3.2-tet)] 2+ , taken as a reference, are resumed in Table 1 .…”

Section: Resultsmentioning

confidence: 99%

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Fluorogenic Detection of Sulfite in Water by Using Copper(II) Azacyclam Complexes

et al. 2022

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Copper(II) azacyclam complexes (azacyclam = 1,3,5,8,12-pentaazacyclotetradecane) containing naphthyl or dansyl subunits can be prepared by template synthesis involving proper sulfonamide derivatives as locking fragments. The macrocyclic complexes are very poorly emissive due to the fluorescence-quenching behavior displayed by Cu2+ ions. However, the fluorescence can be recovered as a result of the decomposition of the complexes, which induces the release of free light-emitting subunits to the solution. This reaction takes place very slowly in neutral water but its rate is increased by the presence of sulfite. Therefore, [Cu(azacyclam)]2+ derivatives have been investigated as simple chemical probes for the fluorogenic detection of sulfite both on laboratory and real samples. Preliminary tests performed on samples of white wine provided sulfite concentration values that are in agreement with those obtained by a standard analytical method.

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Section: Resultssupporting

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Fluorogenic Detection of Sulfite in Water by Using Copper(II) Azacyclam Complexes

et al. 2022

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“…A closely related procedure was used for the preparation of the C2 complex. In this case, a mixture of ethylenediamine, formaldehyde, and Cu(OAc) 2 were heated in methanol, yielding di‐aza‐cyclam complex 6 . Further reaction of 6 with 5 afforded complex C2 .…”

Section: Resultsmentioning

confidence: 95%

Anions as Triggers in Controlled Release Protocols from Mesoporous Silica Nanoparticles Functionalized with Macrocyclic Copper(II) Complexes

Sayed

Milani

Milanese

et al. 2016

Chemistry A European J

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“…Copper complexes [ 1a ] 2+ and [ 1b ] 2+ incorporating a urea subunit are able to recognize oxo anions exploiting the cooperative effect because of the proximity of a coordinatively unsaturated metal center and a hydrogen-bonding donor group. It should be noted that compounds [ 1a ] 2+ and [ 1b ] 2+ were obtained by a template reaction in which ureas were used as “locking fragments”; , therefore, a nitrogen of the urea group is incorporated into the macrocyclic azacyclam framework. This prevents full exploitation of the tendencies of urea moieties to form several hydrogen bonds at the same time (in particular toward Y-shaped anions).…”

Section: Introductionmentioning

confidence: 99%

Oxo-Anion Recognition by Mono- and Bisurea Pendant-Arm Macrocyclic Complexes

et al. 2014

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The novel macrocyclic copper(II) complexes [2](2+) and [3](2+), carrying one or two (nitrophenyl)urea fragments appended to an azacyclam or diazacyclam framework, exploit the hydrogen-bond-forming abilities of the urea subunits, along with the metal-ligand interaction, in the recognition of anionic species. Equilibrium studies in acetonitrile performed on [2](2+) and [3](2+) show that (nitrophenyl)urea pendant arms strongly interact with anionic species such as carboxylates and phosphates, which display both coordinating tendencies toward copper(II) and good affinity toward urea subunits. Stability constants of the adducts are considerably higher than those determined for the interaction of the same anions with a "plain urea" reference compound, confirming the synergistic action of metallomacrocyclic and urea subunits. Complex [2](2+) forms 1:1 adducts with acetate, benzoate, hydrogendiphosphate, and dihydrogen phosphate, while complex [3](2+) interacts with the same anions according to both 1:1 and 1:2 stoichiometries, with the exception of hydrogendiphosphate, which forms only the 1:1 adduct with a distinctly high association constant (log K > 7). Spectrophotometric investigations suggest that oxoanionic species interact with the complexes according to a "bridged" mode, inducing the macrocyclic systems to adopt a scorpionate-like conformation, as confirmed by crystallographic studies on the [3](2+)/succinate adduct.

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Synthesis of novel diazacyclam copper(II) complexes by template reaction involving sulphonamides as locking fragments

Cited by 4 publications

References 52 publications

Fluorogenic Detection of Sulfite in Water by Using Copper(II) Azacyclam Complexes

Fluorogenic Detection of Sulfite in Water by Using Copper(II) Azacyclam Complexes

Anions as Triggers in Controlled Release Protocols from Mesoporous Silica Nanoparticles Functionalized with Macrocyclic Copper(II) Complexes

Oxo-Anion Recognition by Mono- and Bisurea Pendant-Arm Macrocyclic Complexes

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