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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP8574V
MKBC1017V
MKBC1017
01929EJ
08924JH

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Saudari, S. R.; Frail, P. R.; Kagan, C. R.
Applied Physics Letters, 95, 023301-023301 (2009)
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)
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)
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
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)
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