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Fluorene

 

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Fluorene



 
 
Not be confused with fluorone
Fluorone

Fluorone is the basic skeleton for various chemicals, most notably fluorone dyes ....
, or the element
Chemical element

A chemical element is a type of atom that is distinguished by its atomic number; that is, by the number of protons in its atomic nucleus. The term is also used to refer to a pure chemical Chemical substance composed of atoms with the same number of protons....
 fluorine
Fluorine

Fluorine is the chemical element with the symbol F and atomic number 9. Fluorine forms a single bond with itself in elemental form, resulting in the diatomic F2 molecule....
.


Fluorene, or 9H-fluorene, is a polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon

Polycyclic aromatic hydrocarbons are chemical compounds that consist of fused aromatic simple aromatic ring and do not contain heteroatoms or carry substituents....
. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
. It is combustible. It has a violet fluorescence
Fluorescence

Fluorescence is a luminescence that is mostly found as an optical phenomenon in cold bodies, in which the molecular absorption of a photon triggers the emission of a photon with a longer wavelength....
, which gave it its name. It is manufactured artificially, although it occurs in the higher boiling fractions of coal tar
Coal tar

Coal tar is a brown or black liquid of high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal is...
. It is insoluble in water and soluble in benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 and ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
.

Fluorene is used to make dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s, plastic
Plastic

Plastic is the general common term for a wide range of synthetic or semisynthetic organic chemistry solid materials suitable for the manufacture of industrial products....
s, and pesticide
Pesticide

A pesticide is a substance or mixture of substances used to kill a pest .A pesticide may be a chemical substance, biological agent , antimicrobial, disinfectant or device used against any pest ....
s.






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Encyclopedia


Not be confused with fluorone
Fluorone

Fluorone is the basic skeleton for various chemicals, most notably fluorone dyes ....
, or the element
Chemical element

A chemical element is a type of atom that is distinguished by its atomic number; that is, by the number of protons in its atomic nucleus. The term is also used to refer to a pure chemical Chemical substance composed of atoms with the same number of protons....
 fluorine
Fluorine

Fluorine is the chemical element with the symbol F and atomic number 9. Fluorine forms a single bond with itself in elemental form, resulting in the diatomic F2 molecule....
.


Fluorene, or 9H-fluorene, is a polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon

Polycyclic aromatic hydrocarbons are chemical compounds that consist of fused aromatic simple aromatic ring and do not contain heteroatoms or carry substituents....
. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
. It is combustible. It has a violet fluorescence
Fluorescence

Fluorescence is a luminescence that is mostly found as an optical phenomenon in cold bodies, in which the molecular absorption of a photon triggers the emission of a photon with a longer wavelength....
, which gave it its name. It is manufactured artificially, although it occurs in the higher boiling fractions of coal tar
Coal tar

Coal tar is a brown or black liquid of high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal is...
. It is insoluble in water and soluble in benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 and ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
.

Fluorene is used to make dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s, plastic
Plastic

Plastic is the general common term for a wide range of synthetic or semisynthetic organic chemistry solid materials suitable for the manufacture of industrial products....
s, and pesticide
Pesticide

A pesticide is a substance or mixture of substances used to kill a pest .A pesticide may be a chemical substance, biological agent , antimicrobial, disinfectant or device used against any pest ....
s. It can be found in corn silk and engine exhaust gas
Exhaust gas

Exhaust gas or flue gas is emitted as a result of the combustion of fuels such as natural gas, gasoline/petrol, diesel, fuel oil or coal....
. It is used for production of fluorenone
Fluorenone

Fluorenone is an aromatic organic compound with the chemical formula C13H8O. It is used to make antimalaria drugs.It can be produced from fluorene via oxidation ....
 and fluorene-9-methanol.

Poly(fluorene) is commonly used as a luminophore
Luminophore

A luminophore is an atom or atomic grouping in a chemical compound that manifests luminescence. There exist organic and inorganic luminophores. It should be stressed that the correct, textbook terminology is luminophore, not lumophore, although the latter term has been frequently but erroneously used in the chemical literature....
 in organic light-emitting diode
Organic light-emitting diode

An Organic Light Emitting Diode , also Light Emitting Polymer and Organic Electro Luminescence , is any Light Emitting Diode whose Emission electroluminescence layer is composed of a film of organic compounds....
s. Fluorene copolymers are being investigated as materials for solar cell
Solar cell

A solar cell or photovoltaic cell is a device that converts sunlight directly into electricity by the photovoltaic effect. Sometimes the term solar cell is reserved for devices intended specifically to capture energy from sunlight, while the term photovoltaic cell is used when the source is unspecified....
s.

The protons in the 9-position of the fluorene ring are acidic (pKa
PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
 = 22.6 in DMSO
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
) and removal of one of them with a base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
, such as sodium hydroxide
Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
, leads to the stable fluorenyl anion, which is aromatic
Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
 and has an intense orange colour. The anion is a nucleophile
Nucleophile

In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding electrons. Because nucleophiles donate electrons, they are by definition Lewis bases ....
 and most electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
s react with it by adding to the 9-position. For example, fluorenol
Fluorenol

Fluorenol is an alcohol derivative of fluorene.References...
, the alcohol of fluorene, is created when a hydroxyl group is placed in the 9-position.

9-Fluorenylmethyl chloroformate (Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc) protecting group
Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction....
 on amines in peptide synthesis
Peptide synthesis

In organic chemistry, peptide synthesis is the production of peptides, which are organic compounds in which multiple amino acids are linked via peptide bonds which are also known as amide bonds....
.

External links

  • in the National Institute of Standards and Technology database.