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771481

Sigma-Aldrich

N, N′-Dimethyl-3,4,9,10-perylenedicarboximide

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H14N2O4
CAS Number:
5521-31-3
Molecular Weight:
418.40
EC Number:
226-866-1
MDL number:
MFCD00071975
UNSPSC Code:
12352103
PubChem Substance ID:
329767499
NACRES:
NA.23

assay

98%

form

powder

mp

>400 °C

λmax

522 nm in dichloromethane

semiconductor properties

N-type (mobility=10-5 cm2/V·s)

SMILES string

CN1C(=O)c2ccc3c4ccc5C(=O)N(C)C(=O)c6ccc(c7ccc(C1=O)c2c37)c4c56

InChI

1S/C26H14N2O4/c1-27-23(29)15-7-3-11-13-5-9-17-22-18(26(32)28(2)25(17)31)10-6-14(20(13)22)12-4-8-16(24(27)30)21(15)19(11)12/h3-10H,1-2H3

InChI key

PJQYNUFEEZFYIS-UHFFFAOYSA-N

General description

N, N′-Dimethyl-3,4,9,10-perylenedicarboximide (Me-PTCDI) is a perylene derivative that can be used as a thermally stable material in the development of an n-type semiconductor device. It has the capacity to have an ordered growth on a variety of substrates. Its conductivity with respect to the frequency tends to increase at different temperatures.[1][2]

Application

Me-PTCDI can be used in the preparation of the hole transporting layers (HTLs), which can further be utilized in the fabrication of perovskite photovoltaic (PPV) cells.[3][4]
This material is air-stable n-type organic semiconductor. These materials also exhibit high thermal stability. Additionally; PBI derivatives have been used for decades as organic high-performance pigments with color shades from red; via maroon; to black.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL8974

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AC electrical conductivity and dielectric relaxation studies on n-type organic thin films of N, N?-Dimethyl-3, 4, 9, 10-perylenedicarboximide (DMPDC)
Qashou SI, et al.
Physica B: Condensed Matter, 525(1), 159-163 (2017)
The photovoltaic effect in a heterojunction of molybdenyl phthalocyanine and perylene dye
Signerski R
Journal of Non-Crystalline Solids, 352(40-41), 4319-4324 (2006)
Hong-Mei Zhao et al.
Journal of the American Chemical Society, 131(43), 15660-15668 (2009-10-29)
Quantum chemical protocols explaining the crystal structures and the visible light absorption properties of 3,4:9,10-perylene tetracarboxylic acid bisimide (PBI) derivates are proposed. Dispersion-corrected density functional theory has provided an intermolecular potential energy of PBI dimers showing several energetically low-lying minima
Interface energetics in organo-metal halide perovskite-based photovoltaic cells
Schulz P, et al.
Energy & Environmental Science, 7(4), 1377-1381 (2014)
The lowest energy Frenkel and charge-transfer excitons in quasi-one-dimensional structures: application to MePTCDI and PTCDA crystals
Hoffmann M, et al.
Chemical Physics, 258(1), 73-96 (2000)

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