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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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Park, S.K.; Jackson, T.N.; Anthony, J.E.; Mourey, D.A.
Applied Physics Letters, 91, 063514-063514 (2007)
An Ultrasensitive Organic Semiconductor NO2 Sensor Based on Crystalline TIPS-Pentacene Films.
Wang Z, et al.
Advanced Materials, 29(38), 1703192-1703192 (2017)
Trilayer hybrid structures for highly efficient THz modulation.
Song M, et al.
Optics Express, 26(19), 25315-25321 (2018)
Flexible spray-coated TIPS-pentacene organic thin-film transistors as ammonia gas sensors.
Yu X, et al.
Journal of Material Chemistry C, 1(40), 6532-6535 (2013)
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Metal-Organic Complexes for Doping

Highly reducing or oxidizing species enhance organic semiconductor conductivity by reducing charge-carrier injection barriers.

Silylethyne-substituted Pentacenes

Silylethyne substitution offers an opportunity to tune solubility for application-specific needs and self-assembly for electronic performance and has yielded semiconductors with excellent device performance.

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 Organic Transistors

Small molecular weight organic semiconductors are promising for flexible transistor applications in next-gen soft electronics.

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