Fully reversible guest exchange in tetraphosphonate cavitand complexes probed by fluorescence spectroscopy

Biavardi, Elisa; Battistini, Gionata; Montalti, Marco; Yebeutchou, Roger M.; Prodi, Luca; Dalcanale, Enrico

doi:10.1039/b801729h

Cited by 62 publications

(42 citation statements)

References 12 publications

(9 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These results nicely complement and support those reported in solution [31] and in the solid-state [18] for Tiiii cavitands. According to the results presented here, this selectivity arises from simultaneous formation of two stable hydrogen bonds.…”

Section: Discussionsupporting

confidence: 80%

Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

Kalenius

Neitola

Suman

et al. 2010

J. Am. Soc. Mass Spectrom.

Self Cite

View full text Add to dashboard Cite

The H-bonding in alkylammonium complexes of phosphonate cavitands were studied by mass spectrometric methods and theoretical calculations. The alkylammonium ions included primary, secondary, and tertiary methyl-and ethylammonium ions. Their complexation with mono-, tetra-, and two di-phosphonate cavitands, which differ according to the number and position of H-bond acceptor P ϭ O groups, was evaluated by using different competition experiments, energy-resolved CID, gas-phase H/D-exchange, and ligand-exchange reactions, together with ab initio theoretical optimization of the complexes. The phosphonate cavitands with two or more adjacent P ϭ O groups were found to be selective towards secondary alkylammonium ions, due to simultaneous formation of two stable hydrogen bonds. In the ion-molecule reactions (both H/D-and ligand-exchange), the formation of two stable hydrogen bonds was observed either to slow down the reaction or to completely prevent it. This was, however, limited to situations where two hydrogen bonds are formed between the H-bond donor sites of the alkyl ammonium ion and the vicinal H-bond acceptor sites of the cavitand. (J Am Soc Mass Spectrom 2010, 21, 440 -450)

show abstract

Section: Discussionsupporting

confidence: 80%

Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

Kalenius

Neitola

Suman

et al. 2010

J. Am. Soc. Mass Spectrom.

Self Cite

View full text Add to dashboard Cite

show abstract

“…At first, the crystal structures of the complexes formed by tetraphosphonate cavitand Tiiii½C 3 H 7 ;CH 3 ;Ph (15), from now onward referred to as Tiiii (16), with glycine methyl ester and sarcosine hydrochlorides were solved to define and compare type, number, and geometry of host-guest interactions present in the solid state in the two cases. Suitable crystals of both complexes were obtained under the same conditions (i.e., via slow evaporation of a methanol/water solution containing the host in the presence of an excess of guest).…”

Section: Resultsmentioning

confidence: 99%

Exclusive recognition of sarcosine in water and urine by a cavitand-functionalized silicon surface

Biavardi

Tudisco²,

Maffei³

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

View full text Add to dashboard Cite

A supramolecular approach for the specific detection of sarcosine, recently linked to the occurrence of aggressive prostate cancer forms, has been developed. A hybrid active surface was prepared by the covalent anchoring on Si substrates of a tetraphosphonate cavitand as supramolecular receptor and it was proven able to recognize sarcosine from its nonmethylated precursor, glycine, in water and urine. The entire complexation process has been investigated in the solid state, in solution, and at the solid-liquid interface to determine and weight all the factors responsible of the observed specificity. The final outcome is a Si-based active surface capable of binding exclusively sarcosine. The complete selectivity of the cavitand-decorated surface under these stringent conditions represents a critical step forward in the use of these materials for the specific detection of sarcosine and related metabolites in biological fluids. molecular recognition | phosphonate cavitand

show abstract

“…The exact mass values were determined using a LTQ ORBITRAP XL Thermo spectrometer equipped with an electrospray interface. This section only includes the synthesis and characterization of ligand 1 from commercially available 5-amino-1,10-phenanthroline (5), through a modified literature procedure [14] and self-assembly in solution and on a silicon surface; syntheses of tetraphosphonate cavitands Tiiii-A [23] and Tiiii-B without the methyl groups at the upper rim. [24] The NMR and MS spectra of the formation of complexes can be found in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Hierarchical Self‐Assembly of Luminescent Eu^III Complexes on Silicon

et al. 2014

Self Cite

View full text Add to dashboard Cite

We have combined the metal-coordinating features of phenanthroline with the remarkable complexing properties of tetraphosphonate (Tiiii) cavitands towards N-methylammonium salts with the aim of assembling novel luminescent ternary complexes. The formation of such complexes was first tested in solution: the charged sarcosine derivative 1, bearing a phenanthroline moiety, was complexed by the cavitand Tiiii-A, followed by coordination of Eu III -tris(β-diketonate) complex 2. The occurrence of the self-assembly has been proven by NMR spectroscopy, mass spectrometry and photophysical measurements. The transfer of this binding protocol to the surface showed the complete orthogonality of these interac-

show abstract

Fully reversible guest exchange in tetraphosphonate cavitand complexes probed by fluorescence spectroscopy

Abstract: We report here the monitoring of reversible guest inclusion in phosphonate cavitands through a large increase in luminescence intensity caused by the modulation of the exoergonicity of an electron-transfer reaction.

Cited by 62 publications

References 12 publications

Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

Exclusive recognition of sarcosine in water and urine by a cavitand-functionalized silicon surface

Hierarchical Self‐Assembly of Luminescent Eu^III Complexes on Silicon

Contact Info

Product

Resources

About

Fully reversible guest exchange in tetraphosphonate cavitand complexes probed by fluorescence spectroscopy

Abstract: We report here the monitoring of reversible guest inclusion in phosphonate cavitands through a large increase in luminescence intensity caused by the modulation of the exoergonicity of an electron-transfer reaction.

Cited by 62 publications

References 12 publications

Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

Exclusive recognition of sarcosine in water and urine by a cavitand-functionalized silicon surface

Hierarchical Self‐Assembly of Luminescent EuIII Complexes on Silicon

Contact Info

Product

Resources

About

Hierarchical Self‐Assembly of Luminescent Eu^III Complexes on Silicon