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Sigma-Aldrich

6,13-Bis(triisopropylsilylethynyl)pentacene

≥99% (HPLC)

Synonym(s):

TIPS pentacene

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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK6369
MKCK4573
MKCF8901
MKCF2501
MKCD5205

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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)
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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.

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