Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Nishikawa, Takeshi; Torimoto, Tsukasa; Nakanishi, Tetsuya; Osaka, Tetsuya; Ohtani, Bunsho

doi:10.1016/j.cplett.2006.10.106

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Cited by 2 publications

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“…We could suppose that also the lipophilic chains, whose spatial arrangement is in turn influenced by the chiral polar head, contribute to the specific interaction altering the monolayer organization of one enantiomer with respect to the other and favoring homochiral interaction in condensed phases. Recent works showed that a proper modeling of molecular chirality dependent domain shape is not straightforward and involves spontaneous polarization and electric quadrupole density …”

Section: Resultsmentioning

confidence: 99%

Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector

et al. 2015

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Section: Resultsmentioning

confidence: 99%

Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector

et al. 2015

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Control of Stripelike and Hexagonal Self-Assembly of Gold Nanoparticles by the Tuning of Interactions between Triphenylene Ligands

2007

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We describe the self-assembly of gold nanoparticles (Au NPs) protected with newly synthesized discotic liquid crystalline molecules of hexaalkoxy-substituted triphenylene (TP) in mixed toluene/methanol solvent. The stripelike (i.e., 2D consisting of linear 1D in stripe) self-assembly is realized successfully by the aid of pi-pi stacking of TP ligand on Au NPs. The smaller Au NPs with TP (AuTP) or the longer alkyl chain between TP and the gold core provide more free spaces among TP moieties. These spaces allow easy insertion of TP on adjacent AuTPs to lead an interparticle pi-pi interaction to form the stripelike arrangement. The solvent hydrophilicity can also serve as a controlled index to tune arrangement among stripelike, hexagonal close packed (hcp), or disorder. We have changed the solvent hydrophilicity by changing the ratio of methanol to toluene, which affects the balance of solution of AuTP (in toluene) and deposition (in methanol). The larger space between TPs and appropriate solvent hydrophilicity realize stripelike self-assembly caused by a strong pi-pi interaction between TPs, which was characterized by TEM, as well as fluorescence, dynamic light scattering, and 1H NMR spectra.

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Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Abstract: Structural and energetic investigations based on semiempirical PM5 and ab initio HF and MP2 calculations suggested that the self-assembled monolayer of an atropisomeric compound, (R)-or (S)-1,1′-binaphthalene-2,2′-dithiol (BNSH), on a gold (111)

Cited by 2 publications

References 20 publications

Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector

Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector

Control of Stripelike and Hexagonal Self-Assembly of Gold Nanoparticles by the Tuning of Interactions between Triphenylene Ligands

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