7,18-dioctyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone

• ChemBase ID: 141082
• Molecular Formular: C40H42N2O4
• Molecular Mass: 614.77248
• Monoisotopic Mass: 614.31445783
• SMILES: CCCCCCCCn1c(=O)c2ccc3c4ccc5c6c4c(ccc6c(=O)n(c5=O)CCCCCCCC)c4c3c2c(cc4)c1=O
• Canonical SMILES: CCCCCCCCn1c(=O)c2ccc3c4c2c(c1=O)ccc4c1c2c3ccc3c2c(cc1)c(=O)n(c3=O)CCCCCCCC
• InChI: InChI=1S/C40H42N2O4/c1-3-5-7-9-11-13-23-41-37(43)29-19-15-25-27-17-21-31-36-32(40(46)42(39(31)45)24-14-12-10-8-6-4-2)22-18-28(34(27)36)26-16-20-30(38(41)44)35(29)33(25)26/h15-22H,3-14,23-24H2,1-2H3
• InChIKey: YFGMQDNQVFJKTR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,18-dioctyl-7,18-diazaheptacyclo[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-dioctyl-7,18-diazaheptacyclo[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: PTCDI-C8; N,N′-Dioctyl-3,4,9,10-perylenedicarboximide; N,N′-二辛基-3,4,9,10-苝二甲酰亚胺

Database IDs

• CAS Number: 78151-58-3
• MDL Number: MFCD08276854
• PubChem SID: 24884668; 162235317
• PubChem CID: 10722480

CALCULATED PROPERTIES

• H Donor: 0
• LogD (pH = 5.5): 9.3654585
• LogD (pH = 7.4): 9.3654585
• Log P: 9.3654585
• Molar Refractivity: 184.035 cm^3
• Polarizability: 74.12496 Å^3
• Polar Surface Area: 74.76 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false
• H Acceptors: 4

PROPERTIES

Physical Property

• Melting Point: >300 °C
• Absorption Wavelength: λmax 526 nm
• Fluorescence: λem ≤533 nm in chloroform
• Semiconductor Properties: N-type (mobility=1.7 cm2/V·s)

Safety Information

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

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C40H42N2O4

DETAILS

Sigma Aldrich - 663913

Application
Electron-transporting (n-type) organic semiconductor suitable for fabrication of n-channel organic field-effect transistors (OFETs).1 OFETs with electron mobilities με ~ 10-2 cm2/ Vs and current on/off ratios on the order of 104 were made based on 1-dimensional nanowires prepared from N,N′-Dioctyl-3,4,9,10-perylenedicarboximide.2
Packaging
1 g in glass bottle