Structural specificity in asymmetric charge-transfer complexation of helicenes

Brown, John M.; Field, Ian P.; Sidebottom, Philip J.

doi:10.1016/s0040-4039(01)92367-6

Cited by 20 publications

(10 citation statements)

References 26 publications

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“…To accomplish the whole synthetic sequence, the last two steps were executed. Both the aromatisation with Ph 3 CBF 4 to afford known [14] 23 and the subsequent demethylation with BBr 3 to afford final 2 proceeded well and rendered the products in excellent yields.…”

Section: Resultsmentioning

confidence: 96%

“…[4a, 14,15] An alternative aromatisation of 17 with triphenylmethanol in trifluoroacetic acid [16] heated at reflux was similarly efficient (69 % yield). The removal of CH 3 groups with BBr 3 completed the whole reaction sequence to provide 1.…”

Section: Resultsmentioning

confidence: 99%

“…in 1,2-dichloroethane (6 mL) was stirred under an atmosphere of argon at 80°C for 3 h. The solvent was removed in vacuo, and the residue was chromatographed on silica gel (petroleum ether/diethyl ether, 95:5) to obtain 23 (136 mg, 96 %) [14] as an amorphous solid. …”

Section: -Methoxyhexahelicene (23)mentioning

confidence: 99%

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A Convenient Route to 2‐Hydroxy‐ and 2,15‐Dihydroxyhexahelicene

et al. 2007

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Abstract2‐Hydroxy‐ and 2,15‐dihydroxyhexahelicene were synthesised from simple benzene and naphthalene building blocks by intramolecular CoI‐ or Ni0‐catalysed [2+2+2] cycloisomerisation of CH3O‐substituted aromatic triynes. This approach avoids vexing photodehydrocyclisation of stilbene‐type precursors, providing thus a useful alternative to classical procedures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

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A Convenient Route to 2‐Hydroxy‐ and 2,15‐Dihydroxyhexahelicene

et al. 2007

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“…The complexation of TAPA with hexahelicene was studied in more detail by Brown et al 126) with NMR-spectroscopy. By measuring the NMR-spectra at different concentrations of donor vs. acceptor the shift in the position of the proton signals can be used for determination of the association constant.…”

Section: Charge-transfer Complexationmentioning

confidence: 99%

Carbohelicenes and heterohelicenes

Laarhoven

Prinsen

1984

Topics in Current Chemistry

266

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“…The use of physical organic and synthetic chemistry was critical to the design and preparation of this dynamic substrate. [12] Patterned substrates containing islands coated with fibronectin were prepared using microcontact printing. [17] Most importantly, the chemical approach described here provides unprecedented control in developing tailored substrates for modulating cell behavior, and will have an impact on programs in bioorganic chemistry, cell biology, and materials science.…”

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confidence: 99%

Asymmetric Induction by Helical Hydrocarbons: [6]- and [5]Helicenes

et al. 2001

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Enantiomerically enriched organic compounds that have been used as chiral catalysts and ligands in asymmetric synthesis possess a heteroatom(s) such as oxygen, nitrogen, sulfur, and phosphorus in addition to carbon and hydrogen atom(s). [1] To the best of our knowledge, no chiral hydrocarbon has ever been used successfully as a chiral ligand or catalyst in asymmetric synthesis. On the other hand, [6]-and compounds, cells resumed migration and proliferated to give a confluent layer, indicating the drugs were not cytotoxic over the time course of this assay.This example establishes that the dynamic substrates are compatible with experiments to modulate cell behavior in situ and in real time. Our results suggest that this method will be broadly useful in assays for screening libraries of drug candidates that have antimigratory effects, and that can block metastasis in cancer. [16] These substrates also offer immediate opportunities for mechanistic studies of cell migration including investigations of the dependence of cell migration on the density and affinity of immobilized ligands. Finally, these active surfaces can be combined with microelectrode arrays to modulate the presentation of ligands on select regions of the substrate and to even immobilize multiple ligands on the substrate.The most important feature of this method is that these substrates are defined at the molecular scale and therefore provide complete control over ligand ± receptor interactions between cell and substrate. The use of physical organic and synthetic chemistry was critical to the design and preparation of this dynamic substrate. This molecular approach is significant because it can be applied to the design of dynamic substrates having other functions, including those that selectively release immobilized ligands and that reversibly modulate the activities of ligands. [17] Most importantly, the chemical approach described here provides unprecedented control in developing tailored substrates for modulating cell behavior, and will have an impact on programs in bioorganic chemistry, cell biology, and materials science.

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Structural specificity in asymmetric charge-transfer complexation of helicenes

Cited by 20 publications

References 26 publications

A Convenient Route to 2‐Hydroxy‐ and 2,15‐Dihydroxyhexahelicene

A Convenient Route to 2‐Hydroxy‐ and 2,15‐Dihydroxyhexahelicene

Carbohelicenes and heterohelicenes

Asymmetric Induction by Helical Hydrocarbons: [6]- and [5]Helicenes

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