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Diazadithia[7]helicenes: synthetic exploration, solid-state structures and properties

(2013) CHEMISTRY-A EUROPEAN JOURNAL. 19(36). p.12077-12085
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Abstract
Diazadithia[7]helicenes were synthesized from the readily available building block ethyl 7-chloro-8-formylthieno[3,2-f]quinoline-2-carboxylate by a Wittig reaction-photocyclization strategy. The helicene core was functionalized by nucleophilic aromatic substitution with a variety of nucleophiles (e.g., O-, N-, and C-centered) and palladium-catalyzed reactions such as Suzuki coupling and Buchwald-Hartwig amination. Racemization studies confirmed that the enantiopure forms of these [7]helicenes are conformationally stable compared to their lower analogues. The solid-state structures of the novel diazadithia[7]helicenes were determined by single-crystal X-ray diffraction. The crystal structures of these azathia[7]helicenes show columnar stacking in antiparallel fashion. The HOMO-LUMO gaps of the new compounds were determined on the basis of electrochemical and optical measurements.
Keywords
cyclization, chiral resolution, helical structures, helicenes, Wittig reactions, CHIRAL DISCRIMINATION, CIRCULAR-DICHROISM, OPTICAL PROPERTIES, HELICENE, DERIVATIVES, ROUTE, THIAHETEROHELICENES, RACEMIZATION, AGGREGATION, RESOLUTION

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Citation

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MLA
Waghray, Deepali, et al. “Diazadithia[7]Helicenes: Synthetic Exploration, Solid-State Structures and Properties.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 19, no. 36, 2013, pp. 12077–85.
APA
Waghray, D., Cloet, A., Van Hecke, K., Mertens, S. F., De Feyter, S., Van Meervelt, L., … Dehaen, W. (2013). Diazadithia[7]helicenes: synthetic exploration, solid-state structures and properties. CHEMISTRY-A EUROPEAN JOURNAL, 19(36), 12077–12085.
Chicago author-date
Waghray, Deepali, Arvid Cloet, Kristof Van Hecke, Stijn FL Mertens, Steven De Feyter, Luc Van Meervelt, Mark Van der Auweraer, and Wim Dehaen. 2013. “Diazadithia[7]Helicenes: Synthetic Exploration, Solid-State Structures and Properties.” CHEMISTRY-A EUROPEAN JOURNAL 19 (36): 12077–85.
Chicago author-date (all authors)
Waghray, Deepali, Arvid Cloet, Kristof Van Hecke, Stijn FL Mertens, Steven De Feyter, Luc Van Meervelt, Mark Van der Auweraer, and Wim Dehaen. 2013. “Diazadithia[7]Helicenes: Synthetic Exploration, Solid-State Structures and Properties.” CHEMISTRY-A EUROPEAN JOURNAL 19 (36): 12077–12085.
Vancouver
1.
Waghray D, Cloet A, Van Hecke K, Mertens SF, De Feyter S, Van Meervelt L, et al. Diazadithia[7]helicenes: synthetic exploration, solid-state structures and properties. CHEMISTRY-A EUROPEAN JOURNAL. 2013;19(36):12077–85.
IEEE
[1]
D. Waghray et al., “Diazadithia[7]helicenes: synthetic exploration, solid-state structures and properties,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 19, no. 36, pp. 12077–12085, 2013.
@article{4090792,
  abstract     = {Diazadithia[7]helicenes were synthesized from the readily available building block ethyl 7-chloro-8-formylthieno[3,2-f]quinoline-2-carboxylate by a Wittig reaction-photocyclization strategy. The helicene core was functionalized by nucleophilic aromatic substitution with a variety of nucleophiles (e.g., O-, N-, and C-centered) and palladium-catalyzed reactions such as Suzuki coupling and Buchwald-Hartwig amination. Racemization studies confirmed that the enantiopure forms of these [7]helicenes are conformationally stable compared to their lower analogues. The solid-state structures of the novel diazadithia[7]helicenes were determined by single-crystal X-ray diffraction. The crystal structures of these azathia[7]helicenes show columnar stacking in antiparallel fashion. The HOMO-LUMO gaps of the new compounds were determined on the basis of electrochemical and optical measurements.},
  author       = {Waghray, Deepali and Cloet, Arvid and Van Hecke, Kristof and Mertens, Stijn FL and De Feyter, Steven and Van Meervelt, Luc and Van der Auweraer, Mark and Dehaen, Wim},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {cyclization,chiral resolution,helical structures,helicenes,Wittig reactions,CHIRAL DISCRIMINATION,CIRCULAR-DICHROISM,OPTICAL PROPERTIES,HELICENE,DERIVATIVES,ROUTE,THIAHETEROHELICENES,RACEMIZATION,AGGREGATION,RESOLUTION},
  language     = {eng},
  number       = {36},
  pages        = {12077--12085},
  title        = {Diazadithia[7]helicenes: synthetic exploration, solid-state structures and properties},
  url          = {http://dx.doi.org/10.1002/chem.201300843},
  volume       = {19},
  year         = {2013},
}

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