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699306

Sigma-Aldrich

Pentacene-N-sulfinyl-tert-butylcarbamate

99% (HPLC)

Synonym(s):

13,6-(Epithioimino)pentacene-16-carboxylic acid, 6,13-dihydro-, tert butyl ester, 15-oxide

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About This Item

Empirical Formula (Hill Notation):
C27H23NO3S
CAS Number:
794586-44-0
Molecular Weight:
441.54
UNSPSC Code:
12352103
PubChem Substance ID:
329762123
NACRES:
NA.23

assay

99% (HPLC)

form

solid

mp

>300 °C

solubility

THF: soluble 1 mg/mL
ethanol: slightly soluble 1 mg/mL
isopropanol: slightly soluble 1 mg/mL
methanol: slightly soluble 1 mg/mL

SMILES string

CC(C)(C)OC(=O)N1C2c3cc4ccccc4cc3C(c5cc6ccccc6cc25)S1=O

InChI

1S/C27H23NO3S/c1-27(2,3)31-26(29)28-24-20-12-16-8-4-6-10-18(16)14-22(20)25(32(28)30)23-15-19-11-7-5-9-17(19)13-21(23)24/h4-15,24-25H,1-3H3

InChI key

VQUHUWBRYQBGLV-UHFFFAOYSA-N

Application

Photopatternable pentacene precursor highly solube in apolar organic solvents (halogenated solvents, THF). Converted to pentacene in thin (e.g. spin-cast) films by heating under N2 atmosphere for one hour at 150 °C. Spin-coated thin films of the pentacene precursor can be patterned by exposure to UV light in the presence of a photoacid generator (e.g. 531014), followed by a brief heating (5 min. at 130 °C and washing away of an un-converted precursor. Organic thin film transistors fabricated by solution processing of this precursor showed mobilities of 0.13 cm2V-1s-1 and on/off ratio 2 x 105.[1]

pictograms

Environment
GHS09

signalword

Warning

hcodes

H400

Hazard Classifications

Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
01517HJ
01417HJ

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Kevin P Weidkamp et al.
Journal of the American Chemical Society, 126(40), 12740-12741 (2004-10-08)
We demonstrate that modifying pentacene to incorporate an acid-labile moiety into its molecular structure leads to a new precursor that can be easily deposited, photopatterned, and processed via wet-chemical methods to produce organic semiconducting devices exhibiting good electrical characteristics. Acidic

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