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The taming of Clar's hydrocarbon


Valenta, Leoš; Juricek, Michal (2022). The taming of Clar's hydrocarbon. Chemical Communications, 58(78):10896-10906.

Abstract

Triangulene is the smallest non-Kekulé graphene fragment known as Clar's hydrocarbon. Due to its open-shell electronic structure, triangulene is a promising molecular building block of carbon-based organic materials for spintronics and quantum molecular science. It comprises six benzenoid rings arranged in a triangular shape with two unpaired electrons delocalized over the entire conjugated core, making this molecule highly reactive. A triplet ground state is predicted for this hydrocarbon by Ovchinnikov's rule, or Lieb's theorem, in accord with Hund's rule. The pioneering work on triangulene was performed almost 70 years ago by Erich Clar, who attempted to prepare the pristine compound. Since then, several synthetic approaches to prepare this molecule have been exploited. The extreme reactivity of triangulene can be circumvented using on-surface techniques or by installation of sterically demanding substituents, which kinetically stabilize the diradical core against oligomerization in solution. The first two examples of a persistent derivative of triangulene were simultaneously and independently developed last year. This article presents a historical development in the synthesis of triangulene and its derivatives and outlines possible future applications in ferromagnetic materials, electrically conductive polymers or quantum computing.

Abstract

Triangulene is the smallest non-Kekulé graphene fragment known as Clar's hydrocarbon. Due to its open-shell electronic structure, triangulene is a promising molecular building block of carbon-based organic materials for spintronics and quantum molecular science. It comprises six benzenoid rings arranged in a triangular shape with two unpaired electrons delocalized over the entire conjugated core, making this molecule highly reactive. A triplet ground state is predicted for this hydrocarbon by Ovchinnikov's rule, or Lieb's theorem, in accord with Hund's rule. The pioneering work on triangulene was performed almost 70 years ago by Erich Clar, who attempted to prepare the pristine compound. Since then, several synthetic approaches to prepare this molecule have been exploited. The extreme reactivity of triangulene can be circumvented using on-surface techniques or by installation of sterically demanding substituents, which kinetically stabilize the diradical core against oligomerization in solution. The first two examples of a persistent derivative of triangulene were simultaneously and independently developed last year. This article presents a historical development in the synthesis of triangulene and its derivatives and outlines possible future applications in ferromagnetic materials, electrically conductive polymers or quantum computing.

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Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > Electronic, Optical and Magnetic Materials
Physical Sciences > Ceramics and Composites
Physical Sciences > General Chemistry
Physical Sciences > Surfaces, Coatings and Films
Physical Sciences > Metals and Alloys
Physical Sciences > Materials Chemistry
Uncontrolled Keywords:Materials Chemistry, Metals and Alloys, Surfaces, Coatings and Films, General Chemistry, Ceramics and Composites, Electronic, Optical and Magnetic Materials, Catalysis
Language:English
Date:1 January 2022
Deposited On:10 Jan 2023 14:23
Last Modified:29 Mar 2024 02:37
Publisher:Royal Society of Chemistry
ISSN:1359-7345
OA Status:Hybrid
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/d2cc03720c
PubMed ID:36098074
Project Information:
  • : FunderH2020
  • : Grant ID716139
  • : Project TitleSpin-Delocalization with a Twist: Chiral Open-Shell Helices
  • : FunderSNSF
  • : Grant IDPZ00P2_148043
  • : Project Title
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)