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802123

Sigma-Aldrich

6,6′-Dibromoisoindigo

Synonym(s):

6-Bromo-3-(6-bromo-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one

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About This Item

Empirical Formula (Hill Notation):
C16H8Br2N2O2
CAS Number:
1147124-21-7
Molecular Weight:
420.05
UNSPSC Code:
12352103
PubChem Substance ID:
329768730
NACRES:
NA.23

Assay

98%

Quality Level

100

form

powder

mp

>300 °C

SMILES string

O=C1NC2=C(C=CC(Br)=C2)/C1=C3C(NC4=C\3C=CC(Br)=C4)=O

InChI

1S/C16H8Br2N2O2/c17-7-1-3-9-11(5-7)19-15(21)13(9)14-10-4-2-8(18)6-12(10)20-16(14)22/h1-6H,(H,19,21)(H,20,22)/b14-13+

InChI key

TWTPKJYUWWAHQJ-BUHFOSPRSA-N

Application

Electron accepting building block for the preparation of electroactive materials for organic electronics.

Pictograms

Environment
GHS09

Hazard Statements

H411

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Chronic 2

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
MKBW2122V

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Ting Lei et al.
Journal of the American Chemical Society, 133(16), 6099-6101 (2011-04-07)
Two conjugated polymers, IIDDT and IIDT, based on an isoindigo core were developed for organic field-effect transisitors. Investigation of their field-effect performance indicated that IIDDT exhibited air-stable mobility up to 0.79 cm(2) V(-1) s(-1), which is quite high among polymer
Ergang Wang et al.
Journal of the American Chemical Society, 133(36), 14244-14247 (2011-08-19)
A new, low-band-gap alternating copolymer consisting of terthiophene and isoindigo has been designed and synthesized. Solar cells based on this polymer and PC(71)BM show a power conversion efficiency of 6.3%, which is a record for polymer solar cells based on
Yi Ren et al.
ACS applied materials & interfaces, 6(16), 14533-14542 (2014-08-05)
We designed and synthesized a series of isoindigo-based derivatives to investigate how chemical structure modification at both the 6,6'- and 5,5'-positions of the core with electron-rich and electron-poor moieties affect photophysical and redox properties as well as their solid-state organization.
Jianguo Mei et al.
Organic letters, 12(4), 660-663 (2010-01-27)
Isoindigo, as a new electron acceptor unit for organic electronic materials, was integrated into two low-energy gap oligothiophenes. Optical and electrochemical studies of the newly synthesized oligomers demonstrate broad absorption through the visible spectrum, along with appropriate energy levels, as

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