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Sigma-Aldrich

4-(2,3-Dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine

97% (HPLC)

Synonym(s):

4-(1,3-Dimethyl-2,3-dihydro-1H-benzoimidazol-2-yl)phenyl)dimethylamine, N-DMBI

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About This Item

Empirical Formula (Hill Notation):
C17H21N3
CAS Number:
302818-73-1
Molecular Weight:
267.37
MDL number:
MFCD00222361
UNSPSC Code:
12352103
PubChem Substance ID:
329767862
NACRES:
NA.23

Assay

97% (HPLC)

form

solid

mp

105-110 °C

SMILES string

CN(C)c1ccc(cc1)C2N(C)c3ccccc3N2C

InChI

1S/C17H21N3/c1-18(2)14-11-9-13(10-12-14)17-19(3)15-7-5-6-8-16(15)20(17)4/h5-12,17H,1-4H3

InChI key

AKIIMLCQTGCWQQ-UHFFFAOYSA-N

General description

4-(2,3-Dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine is a semiconducting organic molecule with a π-conjugated polycyclic system. It is a strong electron donor molecule that can be used for n-type doping. It shows conductivity of ~2 × 10−3 S/cm as a dopant. It also acts as a reagent for the reductive transformation of organic compounds.

Application

Air stable n-type dopant for n-channel Organic Thin Film Transistors (OTFTs) and solar cells (OPVs).
It is mainly used as a semiconductor based polymer for the fabrication of electronic devices, which include organic thin film transistors (OTFTs), polymeric solar cells (PSCs) and organic light emitting diodes (OLEDs).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cho, Namchul;
Advanced Engineering Materials, 1, 1148-1153 (2011)
Molecular orbital analysis of selected organic p-type and n-type conducting small molecules
Cagardova D and Vladimir L
Acta Chimica Slovaca, 10(1), 6-16 (2017)
In-situ Crosslinking and n-Doping of Semiconducting Polymers and Their Application as Efficient Electron-Transporting Materials in Inverted Polymer Solar Cells
Cho N, et al.
Advanced Energy Materials, 1(6), 1148-1153 (2011)
Use of a 1 H-benzoimidazole derivative as an n-type dopant and to enable air-stable solution-processed n-channel organic thin-film transistors
Wei P, et al.
Journal of the American Chemical Society, 132(26), 8852-8853 (2010)
François Lapointe et al.
ACS applied materials & interfaces, 11(39), 36027-36034 (2019-09-19)
Although carbon nanotube transistors present outstanding performances based on key metrics, large-scale uniformity and repeatability required in printable electronics depend greatly on proper control of the electrostatic environment. Through a survey of polymer dielectric encapsulants compatible with printing processes, a
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