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666025

Sigma-Aldrich

13,6-N-Sulfinylacetamidopentacene

97%

Synonym(s):

16-Acetyl-6,13-dihydro-15-oxide -13,6-(epithioimino)pentacene, NSFAAP, soluble pentacene precursor

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About This Item

Empirical Formula (Hill Notation):
C24H17NO2S
CAS Number:
454675-76-4
Molecular Weight:
383.46
MDL number:
MFCD08457646
UNSPSC Code:
12352103
PubChem Substance ID:
24884196
NACRES:
NA.23

Assay

97%

form

solid

mp

169-190 °C

solubility

THF: soluble
dioxane: soluble
methylene chloride: soluble

fluorescence

λex 251 nm; λem 498 nm in chloroform

storage temp.

−20°C

SMILES string

CC(=O)N1[C@@H]2c3cc4ccccc4cc3[C@@H](c5cc6ccccc6cc25)S1=O

InChI

1S/C24H17NO2S/c1-14(26)25-23-19-10-15-6-2-4-8-17(15)12-21(19)24(28(25)27)22-13-18-9-5-3-7-16(18)11-20(22)23/h2-13,23-24H,1H3/t23-,24+,28?

InChI key

HIABOOSIYBUBKB-XUEDKKMFSA-N

General description

13,6-N-Sulfinylacetamidopentacene (NSFAAP) is a highly soluble pentacene precursor that can be synthesized by Lewis acid-catalyzed Diels-Alder reaction of pentacene and N-sulfinylacetamide. It can be spin coated to form an organic thin film which can be used in organic electronics.

Application

NSFAAP can be used as a conjugating polymer that can be used in designing of thin film transistors with field mobility of 0.27 cm2V-1s-1 and a threshold voltage parameter of -4.25 V.

Preparation Note

Dried thin films convert to pentacene at 150-200 °C

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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High-performance, solution-processed organic thin film transistors from a novel pentacene precursor
Afzali A, et al.
Journal of the American Chemical Society, 124(30), 8812-8813 (2002)
Ali Afzali et al.
Journal of the American Chemical Society, 124(30), 8812-8813 (2002-07-26)
The Lewis acid-catalyzed Diels-Alder reaction of the organic semiconductor pentacene with N-sulfinylacetamide yields a soluble adduct. Spin-coated thin films of this adduct undergo solid-phase conversion to form thin films of pentacene at moderate temperatures. Organic thin film transistors fabricated by
On-Demand Patterning of Nanostructured Pentacene Transistors by Scanning Thermal Lithography
Shaw JE
Advanced Materials, 25(4), 552-558 (2013)
Enhanced thin-film transistor performance by combining 13, 6-N-sulfinylacetamidopentacene with printed PEDOT: PSS electrodes
Luzio A, et al.
Chemistry of Materials, 23(4), 1061-1069 (2011)
An organic thin film transistor based non-volatile memory with zinc oxide nanoparticles
Lee WK, et al.
Thin Solid Films, 519(15), 5208-5211 (2011)
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