7,18-dioxaheptacyclo[14.6.2.2^{2,5}.0^{3,12}.0^{4,9}.0^{13,23}.0^{20,24}]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone

• ChemBase ID: 79980
• Molecular Formular: C24H8O6
• Molecular Mass: 392.31672
• Monoisotopic Mass: 392.03208798
• SMILES: O1C(=O)c2ccc3c4ccc5c6c4c(ccc6C(=O)OC5=O)c4ccc(c2c34)C1=O
• Canonical SMILES: O=C1OC(=O)c2c3c1ccc1c3c(cc2)c2c3c1ccc1c3c(cc2)C(=O)OC1=O
• InChI: InChI=1S/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H
• InChIKey: CLYVDMAATCIVBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,18-dioxaheptacyclo[14.6.2.2^{2,5}.0^{3,12}.0^{4,9}.0^{13,23}.0^{20,24}]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone; 7,18-dioxaheptacyclo[14.6.2.2^2,^5.0^3,^1^2.0^4,^9.0^1^3,^2^3.0^2^0,^2^4]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• IUPAC Traditional name: 7,18-dioxaheptacyclo[14.6.2.2^{2,5}.0^{3,12}.0^{4,9}.0^{13,23}.0^{20,24}]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone; 7,18-dioxaheptacyclo[14.6.2.2^2,^5.0^3,^1^2.0^4,^9.0^1^3,^2^3.0^2^0,^2^4]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• Synonyms: 1,3,8,10-Tetrahydropyrano[3',4',5':9,10]perylo[3,4-cd]pyran-1,3,8,10-tetraone; 3,4,9,10-Perylenetetracarboxylic dianhydride; PTCDA; Pigment Red 224; Perylene-3,4,9,10-tetracarboxylic dianhydride; 二萘嵌苯-3,4,9,10-四甲酸二酐; 颜料红 224; 苝-3,4,9,10-四羧酸二酐

Database IDs

• CAS Number: 128-69-8
• EC Number: 204-905-3
• MDL Number: MFCD00006916
• Beilstein Number: 57831
• PubChem SID: 162044743; 24898155
• PubChem CID: 67191

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.17208
• LogD (pH = 7.4): 4.17208
• Log P: 4.17208
• Molar Refractivity: 105.7868 cm^3
• Polarizability: 44.457695 Å^3
• Polar Surface Area: 86.74 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C
• Orbital energy: HOMO 6.8 eV; LUMO 4.7 eV
• Semiconductor Properties: N-type (mobility=10-4 cm2/V·s)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (C); 97%; 98%
• Grade: purum
• OPV Device Performance: ITO/CuPc/PTCDA/In2• Short-circuit current density (Jsc): 2 mA/cm2• Open-circuit voltage (Voc): 0.55 V• Fill Factor (FF): 0.35• Power Conversion Efficiency (PCE): 1.8 %
• Empirical Formula (Hill Notation): C24H8O6

DETAILS

Sigma Aldrich - P11255

Application
An n-channel organic semiconductor.1
Packaging
25, 100 g in glass bottle