Fluorene

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Fluorene
Identifiers
CAS number	[86-73-7]
EINECS number	201-695-5
SMILES	C12=CC=CC=C1C(C=CC=C3)=C3C2
Properties
Molecular formula	C13H10
Molar mass	166.223 g/mol
Density	1.202 g/mL
Melting point	116-117 °C
Boiling point	295 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Fluorene, or 9H-fluorene, is a polycyclic aromatic hydrocarbon. It has the form of white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It is combustible. It has a violet fluorescence, which gave it its name. It is manufactured artificially, although it occurs in the higher boiling fractions of coal tar. It is insoluble in water and soluble in benzene and ether.

Fluorene is used to make dyes, plastics, and pesticides. It can be found in corn silk and engine exhaust gas. It is used for production of fluorenone and fluorene-9-methanol.

Poly(fluorene) is commonly used as a luminophore in organic light-emitting diodes. Fluorene copolymers are being investigated as materials for solar cells.

The protons in the 9-position of the fluorene ring are acidic (pK_a = 22.6 in DMSO^[1]) and removal of one of them with a base, such as sodium hydroxide, leads to the stable fluorenyl anion, which is aromatic and has an intense orange colour. The anion is a nucleophile and most electrophiles react with it by adding to the 9-position.

The carbamate ester of 9-hydroxymethylfluorene, 9-fluorenylmethyl carbamate (FMOC), is used a N-terminal protective group in peptide synthesis.

Fluorene should not be confused with fluorone, nor with the element fluorine.

[edit] References

[edit] External links

• National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
• Fluorene in the National Institute of Standards and Technology database.