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663921

Sigma-Aldrich

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

98%

Synonym(s):

PTCDI-C5

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About This Item

Empirical Formula (Hill Notation):
C34H30N2O4
CAS Number:
76372-75-3
Molecular Weight:
530.61
MDL number:
MFCD08276855
UNSPSC Code:
12352103
PubChem Substance ID:
24884669
NACRES:
NA.23

assay

98%

form

solid

mp

>300 °C

λmax

527 nm

fluorescence

λem ≤533 nm in chloroform

semiconductor properties

N-type (mobility~10−4 cm2/V·s)

SMILES string

CCCCCN1C(=O)c2ccc3c4ccc5C(=O)N(CCCCC)C(=O)c6ccc(c7ccc(C1=O)c2c37)c4c56

InChI

1S/C34H30N2O4/c1-3-5-7-17-35-31(37)23-13-9-19-21-11-15-25-30-26(34(40)36(33(25)39)18-8-6-4-2)16-12-22(28(21)30)20-10-14-24(32(35)38)29(23)27(19)20/h9-16H,3-8,17-18H2,1-2H3

InChI key

JNZZCMNXYAOLTO-UHFFFAOYSA-N

General description

N,N′-Dipentyl-3,4,9,10-perylenedicarboximide (PTCDI-C5) belongs to the class of perylene based semiconducting materials that can be used as active compounds in a variety of opto-electronic devices. Its properties include cost efficiency, high mobility of electrons, high molar absorption coefficient, reversible redox properties and good electrochemical properties.

Application

Electron-transporting (n-type) organic semiconductor suitable for fabrication of n-channel organic field-effect transistors (OFETs). 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′-Dipentyl-3,4,9,10-perylenedicarboximide.
PTCDI-C5 can be used for a variety of applications which include liquid crystals, organic thin film transistors (OTFTs), solar cells, photovoltaics and sensors.

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 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sensing properties of the n, n?-dipentyl-3, 4, 9, 10-perylenedicarboximide small molecule for different concentrations and solvents for sensor applications
Gunduz B
Sensor Letters, 13(1), 52-63 (2015)
Investigation of the spectral, optical and surface morphology properties of the N, N?-Dipentyl-3, 4, 9, 10-perylenedicarboximide small molecule for optoelectronic applications
Gunduz B
Polymers For Advanced Technologies, 27(2), 144-155 (2016)
Variable temperature film and contact resistance measurements on operating n-channel organic thin film transistors
Chesterfield RJ, et al.
Journal of Applied Physics, 95(11), 6396-6405 (2004)
Study of structural, optical properties and electronic structure of PTCDI-C5 organic nanostructure
Kurban M and Gunduz B
Chemical Physics Letters, 691(2), 14-21 (2018)
Frank Würthner
Chemical communications (Cambridge, England), (14), 1564-1579 (2004-07-21)
Perylene bisimide dyes and their organization into supramolecular architectures through hydrogen-bonding, metal ion coordination and pi-pi-stacking is discussed; further self-assembly leading to nano- and meso-scopic structures and liquid-crystalline compounds is also addressed.
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