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750042

Sigma-Aldrich

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:
15509-95-2
Molecular Weight:
324.48
MDL number:
MFCD02323391
UNSPSC Code:
12352103
PubChem Substance ID:
329766042
NACRES:
NA.23

assay

97%

form

solid

mp

154-160 °C

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

InChI key

UBHPRZXDFVCNHZ-UHFFFAOYSA-N

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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)
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)
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)
Idzik, K. R.; Beckert, R.; Golba, S.; Ledwon, P.; Lapkowski, M.
Tetrahedron Letters, 51, 2396-2396 (2010)
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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