Structure via PubChem · Public domain (PubChem)
triangulene
Sign in to saveTriangulene (also known as Clar's hydrocarbon) is the smallest triplet-ground-state polybenzenoid. It exists as a biradical with the chemical formula . It was first hypothesized by Czech chemist Erich Clar in 1953. Its first confirmed synthesis was published in a February 2017 issue of Nature Nanotechnology, in a project led by researchers David Fox and Anish Mistry at the University of Warwick in collaboration with IBM. Other attempts by Japanese researchers have been successful only in making substituted triangulene derivatives.
Chemical data
- Formula
- C22H12
- Molecular weight
- 276.3 g/mol
- SMILES
- [CH-]1C=CC2=CC3=C4C(=CC=C3)C=C5C=CC=C6[C+]5C4=C2C1=C6
- InChIKey
- YUXIWEBPPQSVAK-UHFFFAOYSA-N
- XLogP
- 5
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Instance of
- radical
- Subclass of
- chemical compound
- Mass
- 276.093900384
Show 3 more facts
- Commons category
- Triangulene
- canonical SMILES
- c1cc2cc3cccc4c3c-5c2c(c1)[CH]c6c5c(ccc6)[CH]4
- chemical formula
- C₂₂H₁₄
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- [''n'']Triangulenes
- Theory
- Experiments
- References
Triangulene (also known as Clar's hydrocarbon) is the smallest triplet-ground-state polybenzenoid. It exists as a biradical with the chemical formula . It was first hypothesized by Czech chemist Erich Clar in 1953. Its first confirmed synthesis was published in a February 2017 issue of Nature Nanotechnology, in a project led by researchers David Fox and Anish Mistry at the University of Warwick in collaboration with IBM. Other attempts by Japanese researchers have been successful only in making substituted triangulene derivatives.
A six-step synthesis yielded two isomers of dihydrotriangulene which were then deposited on xenon or copper base. The researchers used a combined scanning tunneling and atomic force microscope (STM/AFM) to remove individual hydrogen atoms. The synthesized molecule of triangulene remained stable at high-vacuum low-temperature conditions for four days, giving the scientists plenty of time to characterize it (also using STM/AFM).
Excerpted from Wikipedia’s “triangulene” article, available under the CC BY-SA 4.0 licence.