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768464

Sigma-Aldrich

2,7-Dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone

Synonym(s):

N,N′-(1-Hexyl)-1,4,5,8-naphthalenetetracarboxydiamide, NDI-C6

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About This Item

Empirical Formula (Hill Notation):
C26H30N2O4
CAS Number:
23536-15-4
Molecular Weight:
434.53
MDL number:
MFCD23098734
UNSPSC Code:
12352103
PubChem Substance ID:
329767378
NACRES:
NA.23

Assay

≥97.6%

form

powder

mp

205-210 °C

λmax

380, 360, 342 nm in dichloromethane (lit.)

semiconductor properties

N-type (mobility=0.7 cm2/V·s)

SMILES string

CCCCCCN1C(=O)c2ccc3C(=O)N(CCCCCC)C(=O)c4ccc(C1=O)c2c34

InChI

1S/C26H30N2O4/c1-3-5-7-9-15-27-23(29)17-11-13-19-22-20(14-12-18(21(17)22)24(27)30)26(32)28(25(19)31)16-10-8-6-4-2/h11-14H,3-10,15-16H2,1-2H3

InChI key

QGDZMDFMUJURJD-UHFFFAOYSA-N

General description

2,7-Dihexylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone is a low-molecular weight perylene derivative which is used as a n-type organic semiconductor in field-effect transistors (FETs). They have high electron mobilities and very good on/off current ratios even in the presence of air. They also possess good mechanical properties and good chemical resistance to a wide range of solvents.

Application

Used as an n-type semiconducting material in organic printed electronics.

Features and Benefits

Good thermal stability and low electron injection barrier. They display a smectic phase with columnar arrangement of mesogens inside the layers when cooled from isotropic phase.

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 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL7828

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Xiaowei Zhan et al.
Advanced materials (Deerfield Beach, Fla.), 23(2), 268-284 (2010-12-15)
Organic electron-transporting materials are essential for the fabrication of organic p-n junctions, photovoltaic cells, n-channel field-effect transistors, and complementary logic circuits. Rylene diimides are a robust, versatile class of polycyclic aromatic electron-transport materials with excellent thermal and oxidative stability, high
Wholly aromatic ether-imides. Potential materials for n-type semiconductors.
Dingemans, T. J., Picken, S. J., Murthy, N. S., Mark, P., StClair, T. L., & Samulski, E. T.
Chemistry of Materials, 16(6), 966-974 (2004)
Development of small molecule donors for solution-processed organic solar cells
Payne, A. J., & Welch, G. C.
Material Matters, 9(1), 23-32 (2014)

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