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716006 Sigma-Aldrich

6,13-Bis(triisopropylsilylethynyl)pentacene

≥99% (HPLC)

Synonym: TIPS pentacene

  • CAS Number 373596-08-8

  • Empirical Formula (Hill Notation) C44H54Si2

  • Molecular Weight 639.07

  •  MDL number MFCD15143658

  •  PubChem Substance ID 329763361

  •  NACRES NA.23

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Properties

Related Categories Materials Science, Organic Field Effect Transistor (OFET) Materials, Organic and Printed Electronics, p-Type Organic Semiconductors, p-Type Small Molecules More...
Quality Level   200
assay   ≥99% (HPLC)
mp   276 °C
solubility   acetone: soluble 0.16 wt. % at 23 °C(lit.)
  anisole: soluble 2.03 wt. % at 23 °C(lit.)
  n-butylbenzene: soluble 3.43 wt. % at 23 °C(lit.)
  toluene: soluble 6.57 wt. % at 23 °C(lit.)
density   1.104 g/cm3 at 25 °C
SMILES string   CC(C)[Si](C#Cc1c2cc3ccccc3cc2c(C#C[Si](C(C)C)(C(C)C)C(C)C)c4cc5ccccc5cc14)(C(C)C)C(C)C
InChI   1S/C44H54Si2/c1-29(2)45(30(3)4,31(5)6)23-21-39-41-25-35-17-13-15-19-37(35)27-43(41)40(22-24-46(32(7)8,33(9)10)34(11)12)44-28-38-20-16-14-18-36(38)26-42(39)44/h13-20,25-34H,1-12H3
InChI key   FMZQNTNMBORAJM-UHFFFAOYSA-N

Description

General description

6,13-Bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene) is a conductive polymer that can form organic thin films for a variety of semiconductor applications due to its high charge carrier mobility and stability.

Application

Silyethyne-Substituted Pentacenes

TIPS-pentacene forms a hybrid with (6,6)-phenylC61-butyric acid methyl ester (PCBM) which can be used as an organic layer than can be coated onto a silicon (Si) substrate for the fabrication of a highly efficient terahertz (THz) modulator. It can be used as a piezoresisitive sensor that produces multiple strain sensors (single sensors and sensor arrays). Organic thin-film transistors can be developed by using silver electrodes as dielectric materials and TIPS-pentacene as a semiconducting layer which can be deposited via inkjet printing.

Packaging

1 g in glass bottle

250 mg in glass insert

Legal Information

Material Matters is a trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Metal-Organic Complexes for Doping Organic Semiconductors and Surface Doping

The conductivity of organic semiconductors can be increased, and the barriers to charge-carrier injection from other materials can be reduced, by the use of highly reducing or oxidizing species to n-...
Stephen Barlow and Seth R. Marder
Center for Organic Photonics and Electronics and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
Keywords: Chemical reactions, Deposition, Diffusion, Evaporation, Nitrogen phosphorus detector, Phase transitions, Photovoltaics, Redox Reactions, Reductions, Semiconductor, Solvents, Spectroscopy, Sublimation

Optoelectronic Devices Based on Diketopyrrolopyrrole (DPP)-containing Conjugated Small Molecules

Optoelectronic devices such as light-emitting diodes (LEDs), solar cells, and light-emitting field effect transistors (FETs) that utilize organic materials as their light harvesting and/or charge tra...
Jianhua Liu and Thuc-Quyen Nguyen
Material Matters 7.1
Keywords: Absorption, Alkylations, Applications, Bacterial conjugations, Biochemistry, Brominations, Building blocks, Capabilities, Nucleic acid annealing, Nucleic acid hybridization, Purification, Recombination, Solar cells, Solvents, Spectra, Spectroscopy, Stille coupling, Support, Suzuki coupling, Type, Ultraviolet-Visible spectroscopy

Organic Materials for Thin Film Transistors

Flexible electronic circuits, displays, and sensors based on organic active materials will enable future generations of electronics products that may eventually enter the mainstream electronics marke...
Prof. Zhenan Bao
Material Matters 2007, 2.3, 4.
Keywords: Building blocks, Deposition, Electronics, Nanotubes, Semiconductor

Silylethyne-Substituted Pentacenes

Research into the use of organic semiconductors in field-effect transistors (FETs) began in earnest in the mid-1990s,1 after early exciting results from vapor-deposited small molecule semiconductors....
John E. Anthony*
Material Matters 2009, 4.3, 58.
Keywords: Applications, Capabilities, Crystallization, Deposition, Electronics, Electrophoretic display, Evaporation, Organic electronics, Semiconductor, Separation, Solar cells, Substitutions

Protocols

TIPS Pentacene: Dip Coating Procedure

With the discovery of organic semiconductors more than twenty years ago, researchers have constantly sought materials with superior performance and a lower cost of processing. Soluble semiconductors ...
Keywords: Deposition, Evaporation, Semiconductor, Solvents, Spin coating

Related Content

Alkynes and Acetylenic Building Blocks

We list over 600 alkyne building blocks, including a wide array of propargyl alcohols, acetylenic boron reagents, and halogenated substrates for cross-coupling. Additionally, many of these are termin...
Keywords: Building blocks, Coupling reactions, Cross couplings

Peer-Reviewed Papers
15

References

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