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Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties

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Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties. / Waghray, D.; Cloet, A.; Van Hecke, K. et al.
In: Chemistry - A European Journal, Vol. 19, No. 36, 2013, p. 12077-12085.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Waghray, D, Cloet, A, Van Hecke, K, Mertens, SFL, De Feyter, S, Van Meervelt, L, Van Der Auweraer, M & Dehaen, W 2013, 'Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties', Chemistry - A European Journal, vol. 19, no. 36, pp. 12077-12085. https://doi.org/10.1002/chem.201300843

APA

Waghray, D., Cloet, A., Van Hecke, K., Mertens, S. F. L., De Feyter, S., Van Meervelt, L., Van Der Auweraer, M., & Dehaen, W. (2013). Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties. Chemistry - A European Journal, 19(36), 12077-12085. https://doi.org/10.1002/chem.201300843

Vancouver

Waghray D, Cloet A, Van Hecke K, Mertens SFL, De Feyter S, Van Meervelt L et al. Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties. Chemistry - A European Journal. 2013;19(36):12077-12085. doi: 10.1002/chem.201300843

Author

Waghray, D. ; Cloet, A. ; Van Hecke, K. et al. / Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties. In: Chemistry - A European Journal. 2013 ; Vol. 19, No. 36. pp. 12077-12085.

Bibtex

@article{a2df546a616e480096cf28ce16ff371b,
title = "Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties",
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 = "chiral resolution, cyclization, helical structures, helicenes, Wittig reactions, Chiral resolutions, Helical structures, Helicenes, Nucleophilic aromatic substitution, Palladium-catalyzed reactions, Single crystal x-ray diffraction, Solid-state structures, Wittig reaction, Carboxylation, Chemical compounds, Cyclization, Optical data processing, X ray diffraction, Stereochemistry",
author = "D. Waghray and A. Cloet and {Van Hecke}, K. and S.F.L. Mertens and {De Feyter}, S. and {Van Meervelt}, L. and {Van Der Auweraer}, M. and W. Dehaen",
year = "2013",
doi = "10.1002/chem.201300843",
language = "English",
volume = "19",
pages = "12077--12085",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "36",

}

RIS

TY - JOUR

T1 - Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties

AU - Waghray, D.

AU - Cloet, A.

AU - Van Hecke, K.

AU - Mertens, S.F.L.

AU - De Feyter, S.

AU - Van Meervelt, L.

AU - Van Der Auweraer, M.

AU - Dehaen, W.

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - chiral resolution

KW - cyclization

KW - helical structures

KW - helicenes

KW - Wittig reactions

KW - Chiral resolutions

KW - Helical structures

KW - Helicenes

KW - Nucleophilic aromatic substitution

KW - Palladium-catalyzed reactions

KW - Single crystal x-ray diffraction

KW - Solid-state structures

KW - Wittig reaction

KW - Carboxylation

KW - Chemical compounds

KW - Cyclization

KW - Optical data processing

KW - X ray diffraction

KW - Stereochemistry

U2 - 10.1002/chem.201300843

DO - 10.1002/chem.201300843

M3 - Journal article

VL - 19

SP - 12077

EP - 12085

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 36

ER -