2007
DOI: 10.1016/j.tetlet.2007.01.058
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Synthesis and characterization of new hexahelicene derivatives

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Cited by 41 publications
(20 citation statements)
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“…These torsion angle are smaller than those observed in [6]helicenes (see Figure S15 in the Supporting Information). [45] The edge-to-edge twist angle of the hexacene backbone of 7 is 49.78, which is larger than those of benzannelated pentacenes (41-438), [46] but is much smaller than those observed for the Pascals twisted acenes. [47] These results suggest that peri-benzopolyacene 4 is a realistic target at least in terms of structural and thermodynamic aspects.…”
Section: Resultsmentioning
confidence: 99%
“…These torsion angle are smaller than those observed in [6]helicenes (see Figure S15 in the Supporting Information). [45] The edge-to-edge twist angle of the hexacene backbone of 7 is 49.78, which is larger than those of benzannelated pentacenes (41-438), [46] but is much smaller than those observed for the Pascals twisted acenes. [47] These results suggest that peri-benzopolyacene 4 is a realistic target at least in terms of structural and thermodynamic aspects.…”
Section: Resultsmentioning
confidence: 99%
“…[2] During the last decade, studies have been carried out toward their application in asymmetric synthesis, [3] molecular recognition, [4] and materials science, for example, as liquid crystals, sensors, and dyes. [6] Although useful, this reaction is not suitable for large-scale production because of the high-dilution conditions. [6] Although useful, this reaction is not suitable for large-scale production because of the high-dilution conditions.…”
Section: Junji Ichikawa* Misaki Yokota Takao Kudo and Satoshi Umezakimentioning
confidence: 99%
“…The domino-cyclization-dehydrogenation sequence was extended to the synthesis of [5] and [6]helicenes from difluoroalkene precursors 1 containing naphthalene rings. As we had observed previously that naphthyl-substituted difluoroalkenes underwent the Friedel-Crafts-type cyclization regioselectively at the 1-position of the ring because of electronic effects, [13] we anticipated that the domino cyclization-dehydrogenation of the naphthalene derivative 1 i would lead to the corresponding [5]helicene.…”
Section: Junji Ichikawa* Misaki Yokota Takao Kudo and Satoshi Umezakimentioning
confidence: 99%
“…[12] Indeed, recently, stationary phases incorporating ionic liquid motifs have demonstrated the ability to separate substituted PAH geometric isomers. [13] Hexahelicene ( Figure 1), [14] also known as phenanthro [3,4-c] phenanthrene, is an atropisomeric PAH in which one side of the molecule must lie above the other because of crowding; [15] this helicity constitutes an element of chirality. While stereospecific pharmacological activities [16] renders chirality a major concern in the modern pharmaceutical industry, [17,18] and chiral pesticides have demonstrated stereospecific persistence, [19] little information exists on the enantioselective toxicities or persistence of chiral PAHs although enantiospecific mutagenities were observed with chrysene 1,2-diol-3,4-epoxides [20] and benzo[a]pyrene 4,5-oxides [21] in Salmonella typhimuhum and in Chinese hamster V79 cells.…”
Section: Introductionmentioning
confidence: 99%