Triangulene

Triangulene
Triangulene
Names
Preferred IUPAC name
Dibenzo[cd,mn]pyrene-4,8-diyl
Other names
[3]Triangulene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C22H12/c1-4-13-10-15-6-2-8-17-12-18-9-3-7-16-11-14(5-1)19(13)22(20(15)17)21(16)18/h1-12H
    Key: YUXIWEBPPQSVAK-UHFFFAOYSA-N
  • c1cc2cc3cccc4c3c-5c2c(c1)[CH]c6c5c(ccc6)[CH]4
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).
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Triangulene (also known as Clar's hydrocarbon) is the smallest triplet-ground-state polybenzenoid.[1] It exists as a biradical with the chemical formula C
22H
12.[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]

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).[4]

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "biradical". doi:10.1351/goldbook.B00671
  2. ^ "triangulene | C22H12 | ChemSpider". www.chemspider.com. Retrieved 2017-02-19.
  3. ^ Ball, Philip (February 2017). "Elusive triangulene created by moving atoms one at a time". Nature. 542 (7641): 284–285. Bibcode:2017Natur.542..284B. doi:10.1038/nature.2017.21462. PMID 28202993. S2CID 4398214.
  4. ^ a b Pavliček, Niko; Mistry, Anish; Majzik, Zsolt; Moll, Nikolaj; Meyer, Gerhard; Fox, David J.; Gross, Leo (April 2017). "Synthesis and characterization of triangulene" (PDF). Nature Nanotechnology. 12 (4): 308–311. Bibcode:2017NatNa..12..308P. doi:10.1038/nnano.2016.305. 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.