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Merck
CN

750042

1,3,5-Tris(2-thienyl)benzene

97%

Synonym(s):

1,3,5-Tri(thiophen-2-yl)benzene

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About This Item

Empirical Formula (Hill Notation):
C18H12S3
CAS Number:
Molecular Weight:
324.48
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
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InChI key

UBHPRZXDFVCNHZ-UHFFFAOYSA-N

SMILES string

c1csc(c1)-c2cc(cc(c2)-c3cccs3)-c4cccs4

InChI

1S/C18H12S3/c1-4-16(19-7-1)13-10-14(17-5-2-8-20-17)12-15(11-13)18-6-3-9-21-18/h1-12H

assay

97%

form

solid

mp

154-160 °C

General description

1,3,5-Tris(2-thienyl)benzene is a 1,3,5 tris substituted benzene that has a three dimensional structure which facilitates the preparation of conjugating polymers. It is a branched conductive monomer with electronically attached nodes that provide a suitable support to increase the conductivity of the synthesized polymers.

Application

1,3,5-Tris(2-thienyl)benzene is a trifunctionalized monomer that can be used in the synthesis of conjugated C3-symmetric poly(arylbenzene) polymers. These polymeric materials can further be used in organic photovoltaic devices as well as organic field effect transistors (OFETs) and organic light emitting diodes (OLED) systems.

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Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Idzik, K. R.; Beckert, R.; Golba, S.; Ledwon, P.; Lapkowski, M.
Tetrahedron Letters, 51, 2396-2396 (2010)
Electrochemical and spectral properties of meta-linked 1, 3, 5-tris (aryl) benzenes and 2, 4, 6-tris (aryl)-1-phenoles, and their polymers
Idzik KR, et al.
Electrochimica Acta, 55(24), 7419-7426 (2010)
Shape and size effects in the crystal structures of complexes of 1, 3, 5-trinitrobenzene with some trigonal donors: the benzene-thiophene exchange rule
Thallapally PK, et al.
Tetrahedron, 56(36), 6721-6728 (2000)
Synthesis and Electrochemical Properties of Novel 1, 3, 5-Tris (oligothienyl) benzenes: A New Generation of 3D Reticulating Agents
Cherioux F and Guyard L
Advances in Functional Materials, 11(4), 305-309 (2001)
Synthesis of C3-Symmetric Nano-Sized Polyaromatic Compounds by Trimerization and Suzuki- Miyaura Cross-Coupling Reactions
Kotha S, et al.
European Journal of Organic Chemistry, 2004(19), 4003-4013 (2004)

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Organic materials in optoelectronic devices like LEDs and solar cells are of significant academic and commercial interest.

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