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Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar’s Hydrocarbon Triangulene


Ribar, Peter; Šolomek, Tomáš; Juricek, Michal (2019). Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar’s Hydrocarbon Triangulene. Organic Letters, 21(17):7124-7128.

Abstract

We present to date the most efficient gramscale synthesis of triangulene-4,8-dione and 12-hydroxytriangulene- 4,8-dione, the precursors of Clar’s hydrocarbon, in overall yields >50%. The direct dihydroprecursors of triangulene, obtained upon reduction of triangulene-4,8- dione, were stabilized in a supramolecular complex with a tetracationic cyclophane ExBox4+ and characterized by singlecrystal X-ray crystallography. This result represents the first step in an endeavor to stabilize the fragile core of triangulene in an inclusion complex in solution and solid state.

Abstract

We present to date the most efficient gramscale synthesis of triangulene-4,8-dione and 12-hydroxytriangulene- 4,8-dione, the precursors of Clar’s hydrocarbon, in overall yields >50%. The direct dihydroprecursors of triangulene, obtained upon reduction of triangulene-4,8- dione, were stabilized in a supramolecular complex with a tetracationic cyclophane ExBox4+ and characterized by singlecrystal X-ray crystallography. This result represents the first step in an endeavor to stabilize the fragile core of triangulene in an inclusion complex in solution and solid state.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry
Language:English
Date:6 September 2019
Deposited On:20 Nov 2019 14:53
Last Modified:22 Nov 2019 14:52
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.orglett.9b02683
Project Information:
  • : FunderSNSF
  • : Grant IDPP00P2_170534
  • : Project TitleControl of Spin Interactions in Helical Systems
  • : FunderSNSF
  • : Grant IDPZ00P2_174175
  • : Project TitleThree-Dimensional Molecular Electron Acceptors for Efficient Electron-Transporting Materials
  • : FunderSNSF
  • : Grant IDPZ00P2_148043
  • : Project TitleQuantum Information Processing Devices: Emergence of High-Spin Nanographenes

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