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771627

Sigma-Aldrich

2,9-Bis[(4-methoxyphenyl)methyl]anthra[2,1,9-def:6,5,10-d′e′f′]diisoquinoline-1,3,8,10(2H,9H)tetrone

99%

Synonym(s):

N,N′-Bis(4-methoxybenzyl)perylene-3,4:9,10-bis(dicarboximide)

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About This Item

Empirical Formula (Hill Notation):
C40 H26 N2 O6
Molecular Weight:
630.64
EC Number:
280-472-4
MDL number:
MFCD23160595
UNSPSC Code:
12352103
PubChem Substance ID:
329767509
NACRES:
NA.23

Assay

99%

form

powder

mp

120-130 °C

λmax

527, 490 nm in dichloromethane

semiconductor properties

(mobility=0.5 cm2/V·s)

SMILES string

COc1ccc(CN2C(=O)c3ccc4c5ccc6C(=O)N(Cc7ccc(OC)cc7)C(=O)c8ccc(c9ccc(C2=O)c3c49)c5c68)cc1

InChI

1S/C40H26N2O6/c1-47-23-7-3-21(4-8-23)19-41-37(43)29-15-11-25-27-13-17-31-36-32(40(46)42(39(31)45)20-22-5-9-24(48-2)10-6-22)18-14-28(34(27)36)26-12-16-30(38(41)44)35(29)33(25)26/h3-18H,19-20H2,1-2H3

InChI key

LQDAMBYDGRGJGA-UHFFFAOYSA-N

Application

High electron transporting character (electron mobility on the order of 0.5 cm2 V-1 s-1); Perylenebis(dicarboximide)s (PDIs) can be used as n-type materials for organic fieldeffect transistors (OFETs);
Excellent candidates as electron accepting building blocks for organic photovoltaics (OPVs);
IR transparent pigment for coating application.

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Josh Vura-Weis et al.
Journal of the American Chemical Society, 132(6), 1738-1739 (2010-01-26)
The binding energy and electronic coupling of perylenediimide (PDI) pi-stacked dimers were calculated using M06-2X/6-31++G** as a function of stacking geometry. Due to shallow minima in the potential energy surface, electronic coupling can vary by over an order of magnitude
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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