Fluorene

Fluorene

Chembox new
Name = Fluorene
ImageFile = Fluorene_numbered.png
ImageName =
ImageFile1 = Fluorene-3D-balls.png IUPACName =
Section1 = Chembox Identifiers
CASNo = 86-73-7
EINECS = 201-695-5
SMILES = C12=CC=CC=C1C(C=CC=C3)=C3C2
Section2 = Chembox Properties
Formula = C13H10
MolarMass = 166.223 g/mol
MeltingPt = 116-117 °C
BoilingPt = 295 °C
Density = 1.202 g/mL

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 (pKa = 22.6 in DMSO [Equilibrium acidities in dimethyl sulfoxide solution, F. G. Bordwell, "Acc. Chem. Res."; 1988; 456-463, doi|10.1021/ar00156a004] ) 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.

9-Fluorenylmethyl chloroformate (Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc) protecting group on amines in peptide synthesis.

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

References

External links

* [http://www.npi.gov.au/database/substance-info/profiles/74.html National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet]
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=86-73-7&Units=SI Fluorene] in the National Institute of Standards and Technology database.


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  • Fluorène — Structure du fluorène. Gén …   Wikipédia en Français

  • Fluorene — Flu or*ene, n. (Chem.) A colorless, crystalline hydrocarbon, {C13H10} having a beautiful violet fluorescence; whence its name. It occurs in the higher boiling products of coal tar, and is obtained artificially. [1913 Webster] …   The Collaborative International Dictionary of English

  • fluorène — ● fluorène nom masculin Hydrocarbure aromatique tricyclique C13H10, découvert par Berthelot dans les goudrons de houille et présentant une fluorescence violette …   Encyclopédie Universelle

  • fluorene — fluorenas statusas T sritis chemija formulė (C₆H₄)₂CH₂ atitikmenys: angl. fluorene rus. флуорен …   Chemijos terminų aiškinamasis žodynas

  • fluorene — ˈflu̇(ə)ˌrēn, ˈflōrˌēn, ˈflȯˌrēn noun ( s) Etymology: International Scientific Vocabulary fluor + ene; originally formed as French fluorène : a colorless crystalline cyclic hydrocarbon C13H10 that has a violet fluorescence and that is obtained… …   Useful english dictionary

  • fluorene — /floor een, in, flawr , flohr /, n. Chem. a white, crystalline, water insoluble solid, C13H10, used chiefly in the manufacture of resins and dyes. [1880 85; < F; see FLUOR , ENE] * * * …   Universalium

  • fluorene — noun A polycyclic aromatic hydrocarbon consisting of two benzene rings joined together directly, and also via a methylene bridge; it is used in light emitting diodes …   Wiktionary

  • fluorene — n. chemical substance used in production of dyes …   English contemporary dictionary

  • fluorene — flu·o·rene …   English syllables

  • fluorene — /ˈflʊərin/ (say floouhreen), /flu / (say flooh ) noun a white crystalline aromatic hydrocarbon, C13H10, used in the manufacture of resins and dyes; orthodiphenylene methane …  

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