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797294

Sigma-Aldrich

1,1,2,3,4,5-Hexaphenyl-1H-silole

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Synonym(s):
1,1,2,3,4,5-Hexaphenylsilacyclopenta-2,4-diene, 1,1,2,3,4,5-Hexaphenylsilacyclopentadiene, 1,1,2,3,4,5-Hexaphenylsilole, HPS, Hexaphenylsilacyclopenta-2,4-diene, Hexaphenylsilacyclopentadiene
Empirical Formula (Hill Notation):
C40H30Si
CAS Number:
752-28-3
Molecular Weight:
538.75
MDL number:
MFCD27976827
UNSPSC Code:
12352103
PubChem Substance ID:
329768582
NACRES:
NA.23

Assay

98%

form

solid

mp

188-193 °C

SMILES string

C1(C2=CC=CC=C2)=C(C3=CC=CC=C3)C(C4=CC=CC=C4)=C(C5=CC=CC=C5)[Si]1(C6=CC=CC=C6)C7=CC=CC=C7

InChI

1S/C40H30Si/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)41(35-27-15-5-16-28-35,36-29-17-6-18-30-36)39(37)33-23-11-3-12-24-33/h1-30H

InChI key

QAKMXYFDVPDIPT-UHFFFAOYSA-N

General description

HPS is an aggregation-induced emission (AIE) material for use in the OLED emitting layer. Photolysis and thermolysis of 1,4,5,6,7,7-hexaphenyl-7-silabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (XIb) may lead to the formation of hexaphenylsilacyclopentadiene.

Application

Hexaphenylsilacyclopentadiene may undergo π4s+π2s cycloaddition with ethyl acrylate to form bicyclosilaheptene. The same study reports similar cycloaddition reactions with various dienophiles. The reaction of hexaphenylsilacyclopentadiene with perbenzoic acid yields a mixture of tetraphenylfuran and cis-dibenzoylstilbene.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Synthesis, Light Emission, Nanoaggregation, and Restricted Intramolecular Rotation of 1,1-Substituted 2,3,4,5-Tetraphenylsiloles
Junwu Chen, Charles C. W. Law, Jacky W. Y. Lam, et al
Chemistry of Materials, 15(7), 1535-1546 (2003)
Photochemical and thermal transformations of 7-silabicyclo[2.2.1]Heptadiene and 7-silabicyclo[2.2.1]heptene systems
Balasubramanian R and George MV
Journal of Organometallic Chemistry null
Peracid oxidation and photooxygenation reactions of silacyclopentadienes,
Mahajan MP, et al.
Tetrahedron, 1549-1553 null
Peracid oxidation and photooxygenation reactions of silacyclopentadienes,
Mahajan MP, et al.
Tetrahedron null
Symmetry allowed ?4s+?2s additions silacyclopentadienes
Balasubramanian R and George MV
Tetrahedron null
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