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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.

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic 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 Oct 2024 01:37
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1021/acs.orglett.9b02683
Project Information:
  • Funder: SNSF
  • Grant ID: PP00P2_170534
  • Project Title: Control of Spin Interactions in Helical Systems
  • Funder: SNSF
  • Grant ID: PZ00P2_174175
  • Project Title: Three-Dimensional Molecular Electron Acceptors for Efficient Electron-Transporting Materials
  • Funder: SNSF
  • Grant ID: PZ00P2_148043
  • Project Title: Quantum Information Processing Devices: Emergence of High-Spin Nanographenes
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