Two-dimensional crystalline structures and photochemical behavior of cinnamate monolayers on water surfaces

Weissbuch, Isabelle; Bouwman, Wim G.; Kjær, Kristian; Als‐Nielsen, J.; Lahav, Meir; Leiserowitz, Leslie

doi:10.1002/chir.11

Cited by 11 publications

(6 citation statements)

References 15 publications

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“…These predictions were tested with monolayers on water of the amphiphiles C 18 H 37 OC 6 H 4 CHCHY, Y = CO 2 H, CONH 2 . UV irradiation of the trans acid monolayer yields the mirror dimer, whereas the amide system undergoes trans − cis isomerization.…”

Section: E Topochemical Reactions In Langmuir Filmsmentioning

confidence: 99%

Design and Characterization of Crystalline Thin Film Architectures at the Air−Liquid Interface: Simplicity to Complexity

et al. 2001

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Section: E Topochemical Reactions In Langmuir Filmsmentioning

confidence: 99%

Design and Characterization of Crystalline Thin Film Architectures at the Air−Liquid Interface: Simplicity to Complexity

et al. 2001

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“…These predictions were tested with monolayers on water of the amphiphiles C 18 H 37 OC 6 H 4 CHCHY, Y = CO 2 H and CONH 2 . Indeed, UV irradiation of the trans acid monolayer yields the mirror dimer, whereas the amide system undergoes trans − cis isomerization.…”

Section: Structural Characteristics Of Langmuir Monolayersmentioning

confidence: 99%

From Nucleation to Engineering of Crystalline Architectures at Air−Liquid Interfaces

et al. 2000

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The packing arrangements of Langmuir films on aqueous solution of simple amphiphiles, such as fatty acids, alcohols, amides, and amino acids, are now established to near atomic resolution by the method of grazing incidence X-ray diffraction (GIXD), complemented by various spectroscopic and lattice energy computational techniques. For simple aliphatic chainlike amphiphilic molecules, it is possible to correlate the extent of two-dimensional (2-D) crystallinity of the Langmuir film with molecular interactions, in terms of the nature and length of the hydrophobic chain, the type of hydrophilic headgroup, and the binding properties thereto of solute ions and molecules from the aqueous subphase. The monolayer packing arrangements of amphiphilic molecules can be engineered for the performance of photoinduced topochemical reactions, and characterized by GIXD. Racemic mixtures of amphiphiles can also be engineered, by taking advantage of intermolecular hydrogen bonding, to undergo a spontaneous separation of the left-and right-handed molecules into 2-D chiral crystals at the air-solution interface. The geometry of binding of molecules or ions from the aqueous subphase to the hydrophilic headgroups can be pinpointed by GIXD, in favorable systems. The ordered binding of solutes to the amphiphile monolayer can lead to induced nucleation of oriented organic and inorganic crystals at the solution interface. GIXD has shown that such an induction can occur via even a partial lattice match, or by structural complementarity, sometimes involving a molecular rearrangement of the amphiphiles. It is possible from monolayer-induced crystallization to glean information on the process of nucleation and on the critical size of the nuclei. A variety of different types of crystalline multilayers, composed of waterinsoluble molecules such as bolaform amphiphiles, alkanes, heterosubstituted aromatics, can be formed at the air-solution interface. The number of layers formed and their polymorphic behavior can be controlled, albeit within limits, with the use of tailor-made additives. Their structures can be determined by GIXD, thus providing data on the initial stages of 3-D crystalization. Multilayers, comprising water-insoluble and watersoluble components, assembled in situ at the solution surface leading to thin film supramolecular architectures, have been engineered. These crystals have been found to be oriented vis-à-vis the solution surface and thus amenable to characterization by GIXD and other methods.

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“…In this study our goal is to explore the feasibility of obtaining highly ordered β-strand assemblies at the air−water interface. The crystalline monolayers introduced here represent a new class of ordered assemblies that provide planar scaffolds relevant to a broad spectrum of potential applications in nanometer-scale surface patterning, including catalysis, photoreactive films, optical , and molecular electronic devices, , cell guidance substrates, and long-range alignment of nanocrystals. − A simple and systematic design strategy, coupled with structural characterization involving X-ray diffraction measurements at the air−water interface, provides new insight into the correlation of peptide sequence and the crystalline properties of peptide monolayers.…”

Section: Introductionmentioning

confidence: 99%

Two-Dimensional Order in β-Sheet Peptide Monolayers

et al. 2000

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Amphiphilic peptides comprising alternating hydrophilic and hydrophobic amino acid residues were designed to form super-secondary structures composed of self-assembled β-strands as monolayers at the air−water interface. Insights provided by in situ grazing-incidence X-ray diffraction (GIXD), surface pressure vs area isotherms, and Fourier transform infrared spectroscopy allow structural characterization of the assembled nanostructures and rational correlation with the peptide sequence. Peptides seven to seventeen amino acids in length were found to form crystalline arrays with coherence lengths in the range of 100 to 1000 Å. Two-dimensional registry of the self-assembled peptides was induced by placement of proline residues at the peptide termini. The films were found to intercalate ordered arrays of ions between juxtaposed β-sheet ribbons to generate peptide−ion composite phases.

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Two-dimensional crystalline structures and photochemical behavior of cinnamate monolayers on water surfaces

Cited by 11 publications

References 15 publications

Design and Characterization of Crystalline Thin Film Architectures at the Air−Liquid Interface: Simplicity to Complexity

Design and Characterization of Crystalline Thin Film Architectures at the Air−Liquid Interface: Simplicity to Complexity

From Nucleation to Engineering of Crystalline Architectures at Air−Liquid Interfaces

Two-Dimensional Order in β-Sheet Peptide Monolayers

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