Cavitands

Pinalli, Roberta; Pedrini, Alessandro; Dalcanale, Enrico

doi:10.1016/b978-0-12-409547-2.12512-0

Cited by 4 publications

(3 citation statements)

References 138 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cavitands are programmable synthetic receptors capable of hosting shape complementary guests through specific weak interactions, such as hydrogen bonding, π-π stacking, and CH-π and cation-π interactions [ 1 ]. Their remarkable and versatile molecular recognition properties have been exploited in many different fields, including catalysis [ 2 , 3 , 4 , 5 ], crystal engineering [ 6 ], molecular grippers [ 7 ], amino acids [ 8 , 9 ] and protein recognition [ 10 , 11 ], responsive nanostructures [ 12 , 13 ], and sensing [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Velcrand Functionalized Polyethylene

et al. 2019

View full text Add to dashboard Cite

Velcrands are a specific class of cavitands whose complementary surfaces induce self-dimerization. The insertion of a velcrand as physical cross-linking unit into a polymer is reported. To this purpose, the velcrand was functionalized at the lower rim with an isocyanate group. The functional velcrand was reacted with poly (ethylene-co-(2-hydroxethylmethacrylate)) (PE-HEMA), a polymer equipped with free hydroxyl groups suitable for reaction with the isocyanate group. The obtained functionalized polymer was characterized by nuclear magnetic resonance (NMR), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR), proving the introduction of velcraplexes in the polymer. Films with varying amounts of velcrands were obtained by solution casting and slow evaporation, testifying the processability of the functionalized polymers. The obtained films were used to measure the oxygen barrier properties of the functionalized material.

show abstract

Section: Introductionmentioning

confidence: 99%

Velcrand Functionalized Polyethylene

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Cavitands are a class of abiotic macromolecular receptors based on a resorcinarene scaffold having enforced cavities of molecular dimensions [17,18]. In the design of cavitands, the choice of the bridging groups connecting the phenolic hydroxyls of the resorcinarene scaffold determines shape, rigidity, dimensions, and complexation properties of the resulting cavity [19].…”

Section: Introductionmentioning

confidence: 99%

Probing the Structural Determinants of Amino Acid Recognition: X-Ray Studies of Crystalline Ditopic Host-Guest Complexes of the Positively Charged Amino Acids, Arg, Lys, and His with a Cavitand Molecule

et al. 2018

View full text Add to dashboard Cite

Crystallization of tetraphosphonate cavitand Tiiii[H, CH3, CH3] in the presence of positively charged amino acids, namely arginine, lysine, or histidine, afforded host-guest complex structures. The X-ray structure determination revealed that in all three structures, the fully protonated form of the amino acid is ditopically complexed by two tetraphosphonate cavitand molecules. Guanidinium, ammonium, and imidazolium cationic groups of the amino acid side chain are hosted in the cavity of a phosphonate receptor, and are held in place by specific hydrogen bonding interactions with the P=O groups of the cavitand molecule. In all three structures, the positively charged α-ammonium groups form H-bonds with the P=O groups, and with a water molecule hosted in the cavity of a second tetraphosphonate molecule. Furthermore, water-assisted dimerization was observed for the cavitand/histidine ditopic complex. In this 4:2 supramolecular complex, a bridged water molecule is held by two carboxylic acid groups of the dimerized amino acid. The structural information obtained on the geometrical constrains necessary for the possible encapsulation of the amino acids are important for the rational design of devices for analytical and medical applications.

show abstract

“…Cavitands [ 1 ] are programmable abiotic receptors capable of hosting shape-complementary guests through specific weak interactions, such as hydrogen bonding, π-π stacking, CH-π and cation-π interactions. Their remarkable and versatile molecular recognition properties have been exploited in many different fields, including catalysis [ 2 , 3 , 4 , 5 ], crystal engineering [ 6 ], molecular grippers [ 7 ], protein recognition [ 8 , 9 ], responsive nanostructures [ 10 , 11 ], self-diagnostic polymers [ 12 ] and sensing [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorinated Tetraphosphonate Cavitands

2018

View full text Add to dashboard Cite

Two synthetic protocols for the introduction of fluorine atoms into resorcinarene-based cavitands, at the lower and upper rim, respectively, are reported. Cavitand 1, bearing four fluorocarbon tails, and cavitand 2, which presents a fluorine atom on the para position of a diester phosphonate phenyl substituent, were synthesized and their complexation abilities toward the model guest sarcosine methyl ester hydrochloride were evaluated via NMR titration experiments. The effect of complexation on the 19F NMR resonance of the probe is evident only in the case of cavitand 2, where the inset of the cation-dipole and H-bonding interactions between the P=O bridges and the guest is reflected in a sizable downfield shift of the fluorine probe.

show abstract

Cavitands

Cited by 4 publications

References 138 publications

Velcrand Functionalized Polyethylene

Velcrand Functionalized Polyethylene

Probing the Structural Determinants of Amino Acid Recognition: X-Ray Studies of Crystalline Ditopic Host-Guest Complexes of the Positively Charged Amino Acids, Arg, Lys, and His with a Cavitand Molecule

Fluorinated Tetraphosphonate Cavitands

Contact Info

Product

Resources

About