9-Methylene-fluorene
Names
Preferred IUPAC name
9-Methylidene-9H-fluorene
Other names
Methylenefluorene
9-Methylidenefluorene
Dibenzofulvene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.251.583
UNII
  • InChI=1S/C14H10/c1-10-11-6-2-4-8-13(11)14-9-5-3-7-12(10)14/h2-9H,1H2
    Key: ZYASLTYCYTYKFC-UHFFFAOYSA-N
  • C=C1C2=CC=CC=C2C3=CC=CC=C13
Properties
C14H10
Molar mass 178.234 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

9-Methylene-fluorene or dibenzofulvene (DBF) is a polycyclic aromatic hydrocarbon with chemical formula (C6H4)2C=CH2. It is best known as one product from deprotection of the Fmoc group.[1] It can be prepared by treatment of 9-hydroxymethylfluorene with strong base.[2]

Properties

It is an analog of a 1,1-diphenylethylene. Polymerization of 9-methylene-fluorene produces a π-stacked polymer.[3]

See also

References

  1. ↑ Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry. 37 (22): 3404–3409. doi:10.1021/jo00795a005.
  2. ↑ Nakano, Tamaki; Nakagawa, Osamu; Yade, Tohru; Okamoto, Yoshio (2003). "Solid-State Polymerization of Dibenzofulvene Leading to a Copolymer with Oxygen". Macromolecules. 36 (5): 1433–1435. Bibcode:2003MaMol..36.1433N. doi:10.1021/ma025792r.
  3. ↑ Tamaki Nakano; Kazuyuki Takewaki; Tohru Yade; Yoshio Okamoto (2001). "Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts". J. Am. Chem. Soc. 123 (37): 9182–9183. doi:10.1021/ja0111131. PMID 11552835.
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