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459852

Sigma-Aldrich

9,10-Anthracenedicarbonitrile

97%

Synonym(s):
9,10-Dicyanoanthracene
Empirical Formula (Hill Notation):
C16H8N2
CAS Number:
Molecular Weight:
228.25
Beilstein:
1646384
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

340 °C (lit.)

SMILES string

N#Cc1c2ccccc2c(C#N)c3ccccc13

InChI

1S/C16H8N2/c17-9-15-11-5-1-2-6-12(11)16(10-18)14-8-4-3-7-13(14)15/h1-8H

InChI key

BIOPPFDHKHWJIA-UHFFFAOYSA-N

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General description

9,10-Anthracenedicarbonitrile (DCA, ADC) is an anthracene derivative. Photochemical reactions of DCA in MeCN-MeOH or MeCN-H2O containing hydroxides or methoxides affords 9-methylimino-10-anthracenecarbonitrile. It participates in the generation of nucleophilic α-hydroxymethyl radicals from α-silyl ethers by irradiation. Binding energy of 9,10-anthracenedicarbonitrile adsorbed onto graphene is -1.23eV.

Application

9,10-Anthracenedicarbonitrile may be used as photosensitizer to investigate the photoisomerization of trans-stilbene (TS) in sodium dodecyl sulfate (SDS)/benzyl alcohol (BA)/H2O system.

Packaging

1 g in glass bottle

Storage Class Code

13 - Non 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

Certificate of Analysis

Certificate of Origin

Xia Guo et al.
Journal of colloid and interface science, 283(2), 578-584 (2005-02-22)
Photoisomerization of trans-stilbene (TS) was investigated in sodium dodecyl sulfate (SDS)/benzyl alcohol (BA)/H(2)O systems in order to establish the relationship between the reaction yields and the compositions and structures of molecular organized assemblies. The results show that, in SDS/BA/H(2)O systems...
a-Silyl Ethers as Hydroxymethyl Anion Equivalents in Photoinduced Radical Electron Transfer Additions.
Gutenberger G, et al.
Angewandte Chemie (International Edition in English), 37(5), 660-662 (1998)
Photoinduced Bimolecular Electron Transfer from Cyano Anions in Ionic Liquids.
Boning W, et al.
The Journal of Physical Chemistry B, 119, 14790-14799 (2015)
Steven Bailey et al.
The Journal of chemical physics, 140(5), 054708-054708 (2014-02-12)
To identify families of stable planar anchor groups for use in single molecule electronics, we report detailed results for the binding energies of two families of anthracene and pyrene derivatives adsorbed onto graphene. We find that all the selected derivatives...
The photochemical reactions of 9, 10-anthracenedicarbonitrile and 1, 4-naphthalenedicarbonitrile in acetonitrile in the presence of bases.
Freccero M, et al.
Tetrahedron, 50(7), 2115-2130 (1994)

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