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Sigma-Aldrich

Naphtho[2,3-a]pyrene

technical grade

Synonym(s):

Naphtho[2,1,8-qra]naphthacene

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About This Item

Empirical Formula (Hill Notation):
C24H14
CAS Number:
196-42-9
Molecular Weight:
302.37
MDL number:
MFCD00191469
UNSPSC Code:
12352100
PubChem Substance ID:
24863777

grade

technical grade

mp

272-273 °C (lit.)

SMILES string

c1ccc2cc3c(cc2c1)cc4ccc5cccc6ccc3c4c56

InChI

1S/C24H14/c1-2-5-18-14-22-20(12-17(18)4-1)13-19-9-8-15-6-3-7-16-10-11-21(22)24(19)23(15)16/h1-14H

InChI key

AXSJLZJXXUBRBS-UHFFFAOYSA-N

General description

Naphtho[2,3-a]pyrene (NP) is a polycyclic aromatic hydrocarbon. Its characterization in a bioassay analysis by employing Salmonella typhimurium strain YG1025 by HPLC has been proposed. It is widely employed material for organic electronic devices. Photolysis of naphtho[2,3-a]pyrene radical cations on irradiation with broadband ultraviolet/visible radiation have been investigated by Fourier transform ion cyclotron resonance mass spectroscopy.

Application

Naphtho[2,3-a]pyrene may be used in the following studies:
  • As test compound for the simultaneous mass spectrometric analysis of nonpolar and polar analytes by heat-assisted laser ablation electrospray ionization (HA-LAESI) method.
  • As donor material in the fabrication of organic solar cells (OSCs).
  • As blue and green emitting material in the fabrication of organic light-emitting diodes (OLEDs).
  • As charge transport channel in the fabrication of organic thin-film transistors (OTFTs).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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C Brian France et al.
Journal of the American Chemical Society, 125(42), 12712-12713 (2003-10-16)
Chiral domains have been prepared by evaporation of a two-dimensionally chiral molecule, naphtho[2,3-a]pyrene (NP), onto the hexagonal Au(111) surface in an ultrahigh vacuum environment. High-resolution UHV scanning tunneling microscopy (STM) showed that NP formed chiral domains consisting of only one
Naphtho [2, 3,a] pyrene as an efficient multifunctional organic semiconductor for organic solar cells, organic light-emitting diodes, and organic thin-film transistors.
Kwon J, et al.
Organic Electronics, 11(6), 1103-1110 (2010)
Photon-induced complete dehydrogenation of putative interstellar polycyclic aromatic hydrocarbon cations: Coronene and Naphtho [2, 3-a] pyrene.
Ekern SP, et al.
The Astrophysical Journal, 488(1), L39-L39 (1997)
Anu Vaikkinen et al.
Analytical chemistry, 85(1), 177-184 (2012-12-04)
A heat-assisted laser ablation electrospray ionization (HA-LAESI) method for the simultaneous mass spectrometric analysis of nonpolar and polar analytes was developed. The sample was introduced using mid-infrared laser ablation of a water-rich target. The ablated analytes were ionized with an
C H Marvin et al.
The Science of the total environment, 231(2-3), 135-144 (1999-09-03)
Bioassay-directed fractionation was used to characterise genotoxic polycyclic aromatic hydrocarbons (PAH) of molecular mass 302 amu in organic solvent extracts of coal tar-contaminated sediment from Sydney Harbour, Nova Scotia. A normal phase HPLC technique was employed to separate PAH-rich solvent
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