Triangulene

Triangulene (also known as Clar's Hydrocarbon) is the smallest triplet-ground-state polybenzenoid.[1] It exists as a diradical with the chemical formula C22H12.[2] It was first hypothesized by Czech chemist Erich Clar in 1953.[3] 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.[4] Other attempts by Japanese researchers have been successful only in making substituted triangulene derivatives.[5]

Triangulene
Names
IUPAC name
4H,8H-Dibenzo[cd,mn]pyren-4,8-diyl
Identifiers
3D model (JSmol)
ChemSpider
Properties
C22H12
Molar mass 276.338 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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).[6]

References
  1. "IUPAC Gold Book - biradical". goldbook.iupac.org. Retrieved 2017-02-19.
  2. "triangulene | C22H12 | ChemSpider". www.chemspider.com. Retrieved 2017-02-19.
  3. Ball, Philip (2017-02-16). "Elusive triangulene created by moving atoms one at a time". Nature. 542 (7641): 284–285. doi:10.1038/nature.2017.21462. PMID 28202993.
  4. Pavliček, Niko; Mistry, Anish; Majzik, Zsolt; Moll, Nikolaj; Meyer, Gerhard; Fox, David J.; Gross, Leo (2017-02-13). "Synthesis and characterization of triangulene" (PDF). Nature Nanotechnology. advance online publication (4): 308–311. Bibcode:2017NatNa..12..308P. doi:10.1038/nnano.2016.305. ISSN 1748-3395. PMID 28192389.
  5. Morita, Yasushi; Suzuki, Shuichi; Sato, Kazunobu; Takui, Takeji (2011). "Synthetic organic spin chemistry for structurally well-defined open-shell graphene fragments". Nature Chemistry. 3 (3): 197–204. Bibcode:2011NatCh...3..197M. doi:10.1038/nchem.985. PMID 21336324.
  6. Pavliček, Niko; Mistry, Anish; Majzik, Zsolt; Moll, Nikolaj; Meyer, Gerhard; Fox, David J.; Gross, Leo (2017-02-13). "Synthesis and characterization of triangulene" (PDF). Nature Nanotechnology. advance online publication (4): 308–311. Bibcode:2017NatNa..12..308P. doi:10.1038/nnano.2016.305. ISSN 1748-3395. PMID 28192389.
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