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771635

Sigma-Aldrich

2,9-Dipropylanthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline-1,3,8,10(2H,9H)tetrone

97%

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Synonym(s):
Bis(n-propylimido)perylene, PDI-C3, Perylene-3,4,9,10-tetracarboxylic acid bis(propylimide)
Empirical Formula (Hill Notation):
C30H22N2O4
CAS Number:
59442-38-5
Molecular Weight:
474.51
MDL number:
MFCD09952500
UNSPSC Code:
12352103
PubChem Substance ID:
329767510
NACRES:
NA.23

Assay

97%

form

solid

mp

>300 °C

λmax

524, 488 nm

semiconductor properties

N-type (mobility=0.1-2.1 cm2/V·s)

SMILES string

CCCN1C(=O)c2ccc3c4ccc5C(=O)N(CCC)C(=O)c6ccc(c7ccc(C1=O)c2c37)c4c56

InChI

1S/C30H22N2O4/c1-3-13-31-27(33)19-9-5-15-17-7-11-21-26-22(30(36)32(14-4-2)29(21)35)12-8-18(24(17)26)16-6-10-20(28(31)34)25(19)23(15)16/h5-12H,3-4,13-14H2,1-2H3

InChI key

GEIYCUVJOKJQPO-UHFFFAOYSA-N

General description

2,9-Dipropylanthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline-1,3,8,10(2H,9H)tetrone belongs to the class of perylenebis(dicarboximide) (PDI) that has an electron transporting character. It can be used as an air-stable n-type semiconductor material in organic field effect transistors. It can also be used as an acceptor molecule in organic photovoltaics.

Application

High electron transporting character; Perylenebis(dicarboximide)s (PDIs) can be used as air-stable n-type semiconductor materials for organic fieldeffect transistors (OFETs);
Excellent candidates as electron accepting building blocks for organic photovoltaics (OPVs).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Evolution of the Molecular Organization in Bis (n-propylimido) perylene Films under Thermal Annealing
Kam A, et al.
Chemistry of Materials, 10(1), 172-176 (1998)
Role of water in the molecular reorientation on thermal annealing of bis (n-propylimido) perylene films
Kam AP, et al.
Langmuir, 16(3), 1185-1188 (2000)
Physical vapor deposited films of a perylene derivative: supramolecular arrangement and thermal stability
Fernandes JD, et al.
Materials Research, 20(4), 882-890 (2017)
M Carmen Ruiz Delgado et al.
Journal of the American Chemical Society, 132(10), 3375-3387 (2010-02-20)
Perylene tetracarboxylic diimide (PTCDI) derivatives stand out as one of the most investigated families of air-stable n-type organic semiconductors for organic thin-film transistors. Here, we use density functional theory to illustrate how it is possible to control the charge-transport parameters

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