Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

716006

Sigma-Aldrich

6,13-Bis(triisopropylsilylethynyl)pentacene

≥99% (HPLC)

Synonym(s):

TIPS pentacene

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C44H54Si2
CAS Number:
373596-08-8
Molecular Weight:
639.07
MDL number:
MFCD15143658
UNSPSC Code:
12352103
PubChem Substance ID:
329763361
NACRES:
NA.23

Quality Level

200

Assay

≥99% (HPLC)

form

solid

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

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 is a high-performance soluble organic semiconductor for printed and flexible electronics applications. Material Matters™ 4.3 - Organic and Molecular Electronics Examples include the fabrication of organic field effect transistors (OFETs) with the highest reported switching speeds and field-effect mobilities in its class.
TIPS-pentacene forms a hybrid with (6,6)-phenylC61-butyric acid methyl ester (PCBM) which can be used as an organic layer that 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.

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCK6369
MKCK4573
MKCF8901
MKCF2501
MKCD5205

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Natalie A Pace et al.
Chemical science, 9(11), 3004-3013 (2018-05-08)
We employ a combination of linear spectroscopy, electrochemistry, and transient absorption spectroscopy to characterize the interplay between electron transfer and singlet fission dynamics in polyacene-based dyes attached to nanostructured TiO2. For triisopropyl silylethynyl (TIPS)-pentacene, we find that the singlet fission
Development of inkjet printed strain sensors.
Correia V, et al.
Smart Materials and Structures, 22(10), 105028-105028 (2013)
Degradation of all-inkjet-printed organic thin-film transistors with TIPS-pentacene under processes applied in textile manufacturing.
Castro, HF, et al.
Organic Electronics, 22(10), 12-19 (2015)
An Ultrasensitive Organic Semiconductor NO2 Sensor Based on Crystalline TIPS-Pentacene Films.
Wang Z, et al.
Advanced Materials, 29(38), 1703192-1703192 (2017)
Park, S.K.; Jackson, T.N.; Anthony, J.E.; Mourey, D.A.
Applied Physics Letters, 91, 063514-063514 (2007)
View All Related Papers

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- or p-dope, respectively, the semiconductor.

Silylethyne-Substituted Pentacenes

Silylethyne-Substituted Pentacenes

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 market.

High Crystalline, Solution-Processable Organic Field-Effect Transistors

Dr. Chan and researchers highlight flexible transistors are the building blocks of next-generation soft electronics. Among all the reported material systems that can be fabricated by researchers, such as circuits, biosensors, stretchable displays, and others,1–5 small molecular weight organic semiconductors are among the most promising candidates for flexible transistor applications. For these small molecular weight organic semiconductors, the semiconductor forming the conductive channel dominates the device performance.

See All

Protocols

TIPS Pentacene Dip Coating Procedure

One of the best known and highest performing smallmolecule organic semiconductors is TIPS-Pentacene. TIPS-Pentacene is soluble in a wide range of solvents and does not require a thermal conversion after deposition.

Related Content

Organic Electronics

Organic electronics utilizes organic conductors and semiconductors for applications in organic photovoltaics, organic light-emitting diodes, and organic field-effect transistors.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service