Directive effect of bromine on stilbene photocyclizations. an improved synthesis of [7]helicene

Sudhakar, Anantha R.; Katz, Thomas J.

doi:10.1016/s0040-4039(00)84494-9

Cited by 64 publications

(54 citation statements)

References 18 publications

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“…Heptahelicene was synthesized as described elsewhere. [17] Enantiomeric separation (ee > 99.9 %) was accomplished by HPLC on a Daicel Chiracel OD column and subsequently tested by HPLC using a Chiracel OD-H column. Assignment of the enantiomers was based on circular dichroism (CD) spectra in accordance to Martin and Marchant.…”

Section: Methodsmentioning

confidence: 99%

Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Fasel¹,

Parschau²,

Ernst³

2003

Angew Chem Int Ed

203

179

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Chemie CommunicationsChirality transfer from single molecules into handed supramolecular structures is studied by self-assembly of chiral molecules on solid surfaces. Each "mountain" in the STM image represents a single M heptahelicene molecule on a Cu(111) surface. The P enantiomer forms the mirror-image structure. For more information see the following Communication by Fasel, Ernst, and Parschau.

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Section: Methodsmentioning

confidence: 99%

Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Fasel¹,

Parschau²,

Ernst³

2003

Angew Chem Int Ed

203

179

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“…Heptahelicene was synthesized as described elsewhere 17. Enantiomeric separation ( ee >99.9 %) was accomplished by HPLC on a Daicel Chiracel OD column and subsequently tested by HPLC using a Chiracel OD‐H column.…”

Section: Methodsmentioning

confidence: 99%

Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

2003

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Chiralitätstransfer vom Molekül in die zweidimensionale Schicht wurde durch Rastertunnelmikroskopie beobachtet. Die lateral ausgedehnte Händigkeit in homochiralen Heptahelicen‐Schichten auf Oberflächen von Einkristallen (siehe Bild) resultiert aus der Orientierung der jeweils direkt benachbarten Moleküle. Die intermolekularen Wechselwirkungen sind im Wesentlichen abstoßende Kräfte zwischen den starren Helices, wodurch ein direkter Chiralitätstransfer ermöglicht wird.

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“…The heptahelicene molecules were synthesized as described elsewhere. 12 The two enantiomers, called M-heptahelicene (Minus) and P-heptahelicene (Plus), were separated using high-performance liquid chromatography techniques. 13 For the experiments reported here, only the "left-handed" M-heptahelicene as shown in Fig.…”

Section: Methodsmentioning

confidence: 99%

Orientation of chiral heptahelicene C30H18 on copper surfaces: An x-ray photoelectron diffraction study

Fasel¹,

Cossy²,

Ernst³

et al. 2001

The Journal of Chemical Physics

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The orientation and the intramolecular relaxation due to adsorption of the chiral phenanthrene-derivative heptahelicene, C 30 H 18 , on Cu(lll) and Cu(332) smfaces have been investigated by means of angle-scanned full-hemispherical x-ray photoelectron diffraction. Although the C 1 s diffraction patterns of the adsorbed submonolayer coverage helicene films exhibit scattering anisotropies of less than two percent, a detailed analysis involving simple molecular mechanics calculations of the atomic coordinates, photoelectron diffraction single-scattering cluster calculations and an R-factor analysis permits the determination of the helicene molecular orientation. On Cu(lll), the molecules are found to bind to the substrate surface via their terminal phenanthrene group oriented parallel to the surface plane, while on Cu(332) the three terminal C-6 rings are oriented parallel to the (Ill) terrace plane. Six azimuthal molecular orientations are found to coexist on Cu(lll), on Cu(332), however, the step-molecule interaction leads to a unique azimuthal alignment of the heptahelicene molecules. The heptahelicene on Cu(332) system thus represents a chiral surface with single-phase orientational order.

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Directive effect of bromine on stilbene photocyclizations. an improved synthesis of [7]helicene

Cited by 64 publications

References 18 publications

Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Orientation of chiral heptahelicene C30H18 on copper surfaces: An x-ray photoelectron diffraction study

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