tert-butyl 23-oxo-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-decaene-24-carboxylate

• ChemBase ID: 142833
• Molecular Formular: C27H23NO3S
• Molecular Mass: 441.54142
• Monoisotopic Mass: 441.1398646
• SMILES: CC(C)(C)OC(=O)N1C2c3cc4ccccc4cc3C(S1=O)c1c2cc2ccccc2c1
• Canonical SMILES: O=C(N1S(=O)C2c3c(C1c1c2cc2c(c1)cccc2)cc1c(c3)cccc1)OC(C)(C)C
• InChI: 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
• InChIKey: VQUHUWBRYQBGLV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 23-oxo-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-decaene-24-carboxylate
• IUPAC Traditional name: tert-butyl 23-oxo-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-decaene-24-carboxylate
• Synonyms: 13,6-(Epithioimino)pentacene-16-carboxylic acid, 6,13-dihydro-, tert butyl ester, 15-oxide; Pentacene-N-sulfinyl-tert-butylcarbamate; 可光致图案的可溶性并五苯前体; 并五苯-N-亚磺酰基-氨基甲酸叔丁酯

Database IDs

• CAS Number: 794586-44-0
• PubChem SID: 162237059
• PubChem CID: 58003904

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.2169
• LogD (pH = 7.4): 6.2169
• Log P: 6.2169
• Molar Refractivity: 125.5454 cm^3
• Polarizability: 51.93006 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: slightly soluble1 mg/mL; isopropanol: slightly soluble1 mg/mL; methanol: slightly soluble1 mg/mL; THF: soluble1 mg/mL
• Melting Point: >300 °C

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: 99% (HPLC)
• Empirical Formula (Hill Notation): C27H23NO3S

DETAILS

Sigma Aldrich - 699306

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
Packaging
100, 500 mg in poly bottle
Protocols & Applications
Fabrication of Organic Field Effect Transistor Device Using a Soluble Pentacene Precursor