(1s,12s)-24-acetyl-23λ4-thia-24-azahexacyclo[10.10.2.02,11.04,9.013,22.015,20]tetracosa-2(11),3,5,7,9,13(22),14,16,18,20-decaen-23-one

• ChemBase ID: 141281
• Molecular Formular: C24H17NO2S
• Molecular Mass: 383.46228
• Monoisotopic Mass: 383.09799979
• SMILES: CC(=O)N1S(=O)[C@H]2c3c(cc4c(c3)cccc4)[C@@H]1c1c2cc2c(c1)cccc2
• Canonical SMILES: CC(=O)N1S(=O)[C@@H]2c3c([C@H]1c1c2cc2c(c1)cccc2)cc1c(c3)cccc1
• InChI: 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?
• InChIKey: HIABOOSIYBUBKB-XUEDKKMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1s,12s)-24-acetyl-23λ^4-thia-24-azahexacyclo[10.10.2.0^2,^1^1.0^4,^9.0^1^3,^2^2.0^1^5,^2^0]tetracosa-2(11),3,5,7,9,13(22),14,16,18,20-decaen-23-one
• IUPAC Traditional name: (1s,12s)-24-acetyl-23λ^4-thia-24-azahexacyclo[10.10.2.0^2,^1^1.0^4,^9.0^1^3,^2^2.0^1^5,^2^0]tetracosa-2(11),3,5,7,9,13(22),14,16,18,20-decaen-23-one
• Synonyms: NSFAAP; 16-Acetyl-6,13-dihydro-15-oxide -13,6-(epithioimino)pentacene; soluble pentacene precursor; 13,6-N-Sulfinylacetamidopentacene; 16-乙酰基-6,13-二氢-15-氧化物-13,6-(环硫亚氨基)并五苯; 可溶性并五苯前体; 13,6-N-亚磺酰基乙酰氨基并五苯

Database IDs

• CAS Number: 454675-76-4
• MDL Number: MFCD08457646
• PubChem SID: 162235515; 24884196
• PubChem CID: 16217989

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.7578
• LogD (pH = 7.4): 4.7578
• Log P: 4.7578
• Molar Refractivity: 110.1162 cm^3
• Polarizability: 45.744972 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dioxane: soluble; methylene chloride: soluble; THF: soluble
• Melting Point: 169-190 °C
• Fluorescence: λex 251 nm; λem 498 nm in chloroform

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 51/53
• Safety Statements: 61
• Personal Protective Equipment: Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C24H17NO2S

DETAILS

Sigma Aldrich - 666025

Application
Pentacene precursor highly soluble (>50mg/ml) in apolar solvents (halogenated solvents, THF). Converted to pentacene in thin (e.g. spin-cast) films by heating under N2 atmosphere for 5-15 minutes at 120-200°C. Organic thin-film transistors fabricated by solution processing of this precursor afforded highest mobilities - up to 0.8cm2V-1s-1 - reported for a solution-processed organic semiconductor.1
This material is highly soluble in CHCl3, MeOH, THF, PGMEA, and other solvents that are commonly used in microelectronics processing.
Packaging
100, 200, 500 mg in glass bottle
Preparation Note
Dried thin films convert to pentacene at 150-200 °C
Protocols & Applications
Fabrication of Organic Field Effect Transistor Device Using a Soluble Pentacene Precursor