Luminescent Lanthanoid Calixarene Complexes and Materials

Massi, Massimiliano; Ogden, Mark I.

doi:10.3390/ma10121369

Cited by 33 publications

(16 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The opposite tendency is observed for its thia-analogue [ 58 , 60 , 69 ]. The complexing capacity of the lower thiacalix[4]arene’s phenolic rim is much higher than that of its classical counterpart [ 71 , 72 , 73 ]. This makes the coordination of Tb 3+ ion via lower thiacalix[4]arene’s phenolic rim more thermodynamically favored than its bis-chelation with two diketonate groups [ 69 ].…”

Section: Complex Formation Of 13-diketone Calix[4]arene Derivativmentioning

confidence: 99%

1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

2021

View full text Add to dashboard Cite

The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure–property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.

show abstract

Section: Complex Formation Of 13-diketone Calix[4]arene Derivativmentioning

confidence: 99%

1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

2021

View full text Add to dashboard Cite

show abstract

“…The interactions of amidic oxygens with cations are known for example from calcium-binding proteins [11] or lanthanoid-binding calix [4]arene derivatives. [12] The interaction of cations with urea oxygen acting as an electron pair donor was studied using unsubstituted urea molecules. [13] Nevertheless, urea groups as binding sites in organic receptors indisputably prefers the complexation of anions.…”

Section: Introductionmentioning

confidence: 99%

“…Ester groups are known to bind cations themselves, [10] but there is the possibility of complexation of a cation by the urea oxygens. The interactions of amidic oxygens with cations are known for example from calcium‐binding proteins [11] or lanthanoid‐binding calix[4]arene derivatives [12] . The interaction of cations with urea oxygen acting as an electron pair donor was studied using unsubstituted urea molecules [13] .…”

Section: Introductionmentioning

confidence: 99%

Structurally Forced Ion Binding Affinity: Tetraurea‐Based Macrocycle as a Receptor for Ion Pairs

Ramírez-Cortés

Eigner²,

Cuřínová

et al. 2022

Eur J Org Chem

View full text Add to dashboard Cite

A urea-based complexation site represents a building block customarily used in the design of receptors for anion recognition. Here we report a cyclization driven change of complexation preferences, leading to a urea-based macrocyclic receptor with selectivity for heavier alkali metal cations. Moreover, thorough 1 H and 19 F NMR, HRMS and X-ray diffraction studies of the complexes revealed an inherent capability of the macrocycle to interact with selected ion pairs.

show abstract

“…[7] Among the numerous and various antennas reported in the literature, the family of calixarenes [8] is widely studied as Ln chelator and antenna for more than 30 years. [9] Exhibiting convergent O-donor atoms at the lower rim for Ln coordination and comprising a tetraaryl binding pocket, the para-position can be modified with a sulfonate group which drastically increases its water solubility, [10] allowing the study of their interaction with Ln cations in water, an important prerequisite for bioanalysis. [11] Water soluble Tb complexes of p-sulfonatocalixarene derivatives have been reported to be more luminescent than their Pr, Sm, Eu and Dy counterparts, [12] the very high affinity of the ligand towards Tb ions allowing the detection of this cation at the subppb level in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Supramolecular Assembly of Luminescent Lanthanide Nanoparticles Surface Functionalized by p‐Sulfonato‐Calix[4]arenes with Charged Aromatic Compounds

et al. 2021

View full text Add to dashboard Cite

The surface coordination of p-sulfonato- (C[4]), p-sulfonatothia- (SC[4]) and p-sulfonato-sulfoxocalix [4]arene (SO 2 C[4]) on La 0.9 Tb 0.1 F 3 nanoparticles (TbNP) was investigated by UV-Vis absorption and luminescence spectroscopies. SO 2 C[4] displayed the strongest affinity towards the NPs and a significant antenna effect leading to observation of the characteristic Tb emission bands upon calixarene excitation. NPs decorated by a shell of SO 2 C[4] were prepared and the interaction with rhodamine 6G (R6G) was studied. The progressive addition of R6G resulted in a strong Tb to R6G energy transfer process, as revealed by a long lived emission of R6G upon SO 2 C[4] excitation. The FRET efficiency was almost quantitative (87-90 %), pointing to an average distance of 28 to 32 Å between the R6G and the Tb emitting centres of the NP. An association of one R6G per SO 2 C[4] was deduced with a very strong apparent affinity (K = 2.5 × 10 7 M À 1 ) in water. Similar interactions were observed with paraquat, resulting in TbNP luminescence quenching. In both cases, an unexpected increase of the association constant of the cation with SO 2 C[4] was observed when SO 2 C[4] is anchored at the surface of the NP.

show abstract

Luminescent Lanthanoid Calixarene Complexes and Materials

Cited by 33 publications

References 52 publications

1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

Structurally Forced Ion Binding Affinity: Tetraurea‐Based Macrocycle as a Receptor for Ion Pairs

Investigation of the Supramolecular Assembly of Luminescent Lanthanide Nanoparticles Surface Functionalized by p‐Sulfonato‐Calix[4]arenes with Charged Aromatic Compounds

Contact Info

Product

Resources

About