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367141

Sigma-Aldrich

Selenophene

97%

Synonym(s):

Selenacyclopentadiene, Selenofuran

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About This Item

Empirical Formula (Hill Notation):
C4H4Se
CAS Number:
288-05-1
Molecular Weight:
131.03
MDL number:
MFCD00075487
UNSPSC Code:
12352100
PubChem Substance ID:
24862395
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.58 (lit.)

bp

110-111 °C (lit.)

mp

−30 °C (lit.)

density

1.423 g/mL at 25 °C (lit.)

SMILES string

c1cc[se]c1

InChI

1S/C4H4Se/c1-2-4-5-3-1/h1-4H

InChI key

MABNMNVCOAICNO-UHFFFAOYSA-N

Related Categories

General description

Selenophene is a heterocyclic building block. Synthesis of selenophene-based heteroacenes has been reported. Synthesis of selenophene-thiophene block copolymers has been reported. The electron transmission spectra of selenophene has been recorded in the 0-6eV energy range.

Application

Selenophene may be used:
  • as conjugated linker in the synthesis of organic dyes
  • in the synthesis of selenophene-2-carbonitrile
  • in the synthesis of selenophene diketopyrrolopyrrole polymers
  • as building block for the electrically conducting polyalkyl selenophene

accessory

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Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Flam. Liq. 2 - STOT RE 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

26.6 °F - closed cup

Flash Point(C)

-3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Toshihiro Okamoto et al.
Organic letters, 7(23), 5301-5304 (2005-11-05)
[reaction: see text] A new intramolecular triple cyclization of bis(o-haloaryl)diacetylenes, via dilithiation followed by reaction with chalcogen elements, produces pi-conjugated compounds containing heterole-1,2-dichalcogenin-heterole fused tricyclic skeletons. The subsequent dechalcogenation with copper metal affords a series of thiophene- and selenophene-based heteroacenes.
Jon Hollinger et al.
Journal of the American Chemical Society, 132(25), 8546-8547 (2010-06-08)
Selenophene-thiophene block copolymers were synthesized and studied. The properties of these novel block copolymers are distinct from those of statistical copolymers prepared from the same monomers with a similar composition. Specifically, the block copolymers exhibit broad and red-shifted absorbance features
Dye-sensitized solar cells based on organic sensitizers with different conjugated linkers: furan, bifuran, thiophene, bithiophene, selenophene, and biselenophene.
Li R, et al.
The Journal of Physical Chemistry C, 113(17), 7469-7479 (2009)
Low band gap selenophene-diketopyrrolopyrrole polymers exhibiting high and balanced ambipolar performance in bottom-gate transistors.
Shahid M, et al.
Chemical Science, 3(1), 181-185 (2012)
Journal of the Electrochemical Society, 137, 1827-1827 (1990)
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