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Sigma-Aldrich

Pyrene

98%

Synonym(s):

Benzo[def]phenanthrene

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About This Item

Empirical Formula (Hill Notation):
C16H10
CAS Number:
129-00-0
Molecular Weight:
202.25
Beilstein:
1307225
EC Number:
204-927-3
MDL number:
MFCD00004136
UNSPSC Code:
12352103
PubChem Substance ID:
24851146
NACRES:
NA.23

Quality Level

100

Assay

98%

mp

145-148 °C (lit.)

SMILES string

c1cc2ccc3cccc4ccc(c1)c2c34

InChI

1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H

InChI key

BBEAQIROQSPTKN-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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General description

Aromatic discotic liquid crystals which exhibits photogeneration of electron-hole pair are used widely in light emitting diodes, photovoltaic cells and field effect transistors. Pyrene is an aromatic discotic crystal which is widely used as a fluorescent dye or as an ambipolar charge carrier in Organic Light Emitting Diodes.

Application

Pyrene and its derivatives are electron-donor materials and can be used to prepare electron donor-acceptor systems for energy conversion and light harvesting applications like OLED and solar cells. It can also be used as a probe to determine the critical micellar concentration of surfactants and to study the protein conformation and conformational changes by fluorescence spectroscopy.

Features and Benefits

Long intrinsic fluorescence lifetime, lipophilic hydrocarbon, facilitates charge transport due to the strong p-p interactions in the solid state.π-system does not require protection during functionalization

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Pyrene fluorescence lifetime as a probe for oxygen penetration of micelles.
M W Geiger et al.
Photochemistry and photobiology, 22(6), 273-276 (1975-12-01)
Photoconductivity of liquid crystalline derivatives of pyrene and carbazole.
Sienkowska, Monika J., et al.
Journal of Materials Chemistry, 17(14), 1392-1398 (2007)
S Fischkoff et al.
The Journal of general physiology, 65(5), 663-676 (1975-05-01)
Quenching of pyrene fluorescence by oxygen was used to determine oxygen diffusion coefficients in phospholipid dispersions and erythrocyte plasma membranes. The fluorescence intensity and lifetime of pyrene in both artificial and natural membranes decreases about 80% in the presence of
Youn Sun Kim et al.
Chemical communications (Cambridge, England), 47(31), 8907-8909 (2011-06-18)
A new pyrene-cored π-conjugated molecule has been synthesized through Sonogashira coupling reaction. The single-crystalline microribbon-based FET exhibited the highest mobility of 0.7 cm(2) V(-1) s(-1) (I(on)/I(off) > 10(6)). Single-crystalline microribbons were employed to operate in an organic phototransistor (OPT) under
Ping Huang et al.
Theranostics, 9(20), 5755-5768 (2019-09-20)
Severe multidrug resistance (MDR) often develops in the process of chemotherapy for most small molecule anticancer drugs, which results in clinical chemotherapy failures. Methods: Here, a nanodrug is constructed through the self-assembly of amphiphilic drug-inhibitor conjugates (ADIC) containing a redox-responsive
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