Perforated monolayers:  porous and cohesive monolayers from mercurated calix[6]arenes

Markowitz, Michael A.; Bielski, Roman; Regen, Steven L.

doi:10.1021/ja00230a049

Cited by 46 publications

(30 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Regen and coworkers [61] recently decribed perforated monolayers from calix [6]arenes but molecular recognition by calixarenes at the air-water interface has never been reported. Since calixarenes XIX exhibit metal recognition ability, it was interesting to test if the ability is also found at the air-water interface.…”

Section: Ionophoric Calixarenesmentioning

confidence: 99%

Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

Shinkai

1991

Calixarenes: A Versatile Class of Macrocyclic Compounds

View full text Add to dashboard Cite

Section: Ionophoric Calixarenesmentioning

confidence: 99%

Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

Shinkai

1991

Calixarenes: A Versatile Class of Macrocyclic Compounds

View full text Add to dashboard Cite

“…18−21 The first report on this topic was published by Regen, who coined the concept of perforated monolayers referring to thin film composite membranes of calix [6]arene-based surfactants bearing uniform, oriented, and adjustable nanopores. 22 Subsequently, the interaction properties of calix[n]-arene monolayers with ions at the air−water interface have been investigated. In the first report dealing with the interfacial selective response of calix[n]arene monolayers toward metal ions, published by Shinkai, the interactions of two calix[n]arene ester derivatives with Na + , Li + , and K + ions were investigated.…”

Section: ■ Introductionmentioning

confidence: 99%

Interfacial Binding of Divalent Cations to Calixarene-Based Langmuir Monolayers

et al. 2015

View full text Add to dashboard Cite

The interactions of Langmuir monolayers produced through the self-assembly of an amphiphilic p-carboxycalix[4]arene (1) with a series of divalent, fourth-period transition metals, at the air-water interface, were investigated. Changes in the interfacial behavior of 1 in response to the presence of CuCl2, CoCl2, MnCl2, and NiCl2 were studied by means of Langmuir compression isotherms and Brewster angle microscopy (BAM). The measurements revealed that the self-assembly properties of 1 are significantly affected by Cu(2+) ions. The interactions of 1-based monolayers with Co(2+) and Cu(2+) ions were further investigated by means of synchrotron radiation-based X-ray reflectivity (XRR), X-ray near-total-reflection fluorescence (XNTRF), and grazing incidence X-ray diffraction (GIXD). XNTRF and XRR analyses revealed that the monolayer of 1 binds more strongly to Cu(2+) than Co(2+) ions. In the presence of relatively high concentrations of Cu(2+) ions in the subphase (1.4 × 10(-3) M), XNTRF exhibited anomalous depth profile behavior and GIXD measurements showed considerably strong diffuse scattering. Both measurements suggest the formation of Cu(2+) clusters contiguous to the monolayer of 1.

show abstract

“…In 1988, Regen et al recognized that these macrocyclic amphiphiles could self-assemble at the air-water interface. [3] They reported stable monolayer formation on a Langmuir trough by both mercurated and alkylated calix [6]arenes derivatives. [3] Because these macrocycles have open interior space, they were attractive candidates as supramolecular filters and sensors.…”

Section: Introductionmentioning

confidence: 99%

“…[3] They reported stable monolayer formation on a Langmuir trough by both mercurated and alkylated calix [6]arenes derivatives. [3] Because these macrocycles have open interior space, they were attractive candidates as supramolecular filters and sensors. Numerous attempts were made to stabilize both calix[-n]arene and calix[n]resocinarene monolayers.…”

Section: Introductionmentioning

confidence: 99%

Pyrogallol[4]arenes Show Highly Variable Amphiphilic Behavior at the Air–Water Interface Dependent Upon Side Chain Length and Branching

Daschbach

Kulikov

Long

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

The behavior of pyrogallol[4]arenes (Pgs) substituted with normal and branched alkyl side chains at the air-water interface was examined on a Langmuir trough. The amphiphilic systems studied form stable monolayers when the straight chains are as short as n-propyl. Remarkably, n-propylpyrogallol[4]arene shows a behavior at the air-water interface that is indistinguishable from that of pyrogallolarenes bearing n-hexyl, n-nonyl, and n-dodecyl side chains. There is no report of amphiphilic side-chain-length dependence or Langmuir trough behavior for families of branched alkyl chain calixarenes or resorcinarenes. In the Pg family reported here, Pgs with straight chains (except for methyl and ethyl) behave very similarly to each other and very differently from symmetrical branched chain analogues having the same total number of carbon atoms. For example, the shortest possible branched side chain of a Pg, isopropyl-Pg, forms stable monolayers by a unique molecular subduction mechanism. Isopropyl-Pg (dimethylmethyl side chain, iPrPg) and 3-pentyl-Pg (diethylmethyl side chain, 3-pentylPg) both show high levels of organization, albeit by quite different mechanisms, at the air-water interface. Both iPrPg and 3-pentylPg differ in behavior from 4-heptylPg. Brewster angle microscopy revealed differences in organization of the Pgs that supports the mechanistic suggestions offered herein.

show abstract

Perforated monolayers: porous and cohesive monolayers from mercurated calix[6]arenes

Cited by 46 publications

References 0 publications

Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

Interfacial Binding of Divalent Cations to Calixarene-Based Langmuir Monolayers

Pyrogallol[4]arenes Show Highly Variable Amphiphilic Behavior at the Air–Water Interface Dependent Upon Side Chain Length and Branching

Contact Info

Product

Resources

About