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768677

Sigma-Aldrich

Naphtho[1,2-b:5,6-b′]dithiophene

97%

Synonym(s):

NDT

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About This Item

Empirical Formula (Hill Notation):
C14H8S2
CAS Number:
217-19-6
Molecular Weight:
240.34
MDL number:
MFCD28053549
UNSPSC Code:
12352103
PubChem Substance ID:
329767392
NACRES:
NA.23

Assay

97%

form

solid

mp

153-160 °C

semiconductor properties

P-type (mobility>0.5 cm2/V·s)

SMILES string

C1(C=CS2)=C2C(C=CC3=C4SC=C3)=C4C=C1

InChI

1S/C14H8S2/c1-3-11-12(13-9(1)5-7-15-13)4-2-10-6-8-16-14(10)11/h1-8H

InChI key

MOZTVOICZIVCFC-UHFFFAOYSA-N

General description

Naphtho[1,2-b:5,6-b′]dithiophene (NDT) is a π-conjugated naphthodithiophene derivative that has symmetrical planar structures. It is mainly utilized in the development of semiconductors due to its high charge mobility and high current on/off ratios.[1][2]

Application

NDT has donor-acceptor copolymers which can be used in the fabrication of organic electronic devices such as organic light emitting diodes (OLEDs), organic solar cells (OSCs) and organic field effect transistors (OFETs).[3][4]
This semiconducting material has been used in the synthesis of copolymers that show the highest mobility (>0.5 cm2 /Vs) in an NDT-based OFET device to date.[5]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

768677-BULK:
768677-VAR:
768677-500MG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL7860

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A crystalline D-pi-A organic small molecule with naphtho (1, 2-b: 5, 6-b?) dithiophene-core for solution processed organic solar cells
Dutta P, et al.
Organic Electronics, 13(12), 3183-3194 (2012)
Grant Fraser et al.
Environmental monitoring and assessment, 189(8), 409-409 (2017-07-25)
Dissolved inorganic nitrogen (DIN) movement from Australian sugarcane farms is believed to be a major cause of crown-of-thorns starfish outbreaks which have reduced the Great Barrier Reef coral cover by ~21% (1985-2012). We develop a daily model of DIN concentration
Siqi Liang et al.
Genome biology, 18(1), 10-10 (2017-01-20)
The mechanistic details of most disease-causing mutations remain poorly explored within the context of regulatory networks. We present a high-resolution three-dimensional integrated regulatory network (iRegNet3D) in the form of a web tool, where we resolve the interfaces of all known
Quinoidal Naphtho (1, 2-b: 5, 6-b?) dithiophenes for Solution-Processed n-Channel Organic Field-Effect Transistors
Mori T, et al.
Organic Letters, 16(5), 1334-1337 (2014)
Bret Ericson et al.
The Science of the total environment, 657, 1382-1388 (2019-01-27)
While lead-based paint has been banned for use in residential settings in most high-income countries, it remains commonly available in many low- and middle-income countries (LMICs). Despite its continued availability, little is known about the specific exposure risk posed by
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