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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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
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 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)
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