2-Bromo-5-dodecylthiophene

CAS Number 153561-74-1

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

2-Bromo-5-dodecylthiophene CAS 153561-74-1

Another widely used alkylated thiophenes

Offers great solubility, thermal stability, and film morphology in application of OFETs and OPVs

Overview
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2-Bromo-5-dodecylthiophene (CAS number 153561-74-1), bearing a dodecyl alkyl chain (C₁₂H₂₅) and a bromo function group at both end positions of the thiophene ring, is widely used for the synthesis of semiconducting small molecules, oligomers, and conjugated polymers in the application of organic electronics.

2-Bromo-5-dodecylthiophene is obtained by reacting 5-dodecylthiophene with N-Bromosuccinimide (NBS). The end bromo group provides the functionality for cross coupling or nucleophilic aromatic substitution reactions to offer extended conjugation to the targeted molecules. The long dodecyl alkyl chain offers great solubility thus improves the processability for organic electronics in solutions. Typically, with dodecyl being on the end of the thiophene ring, 2-bromo-5-dodecylthiophene is used as an end-capper especially in the case of OFETs materials.

2-Bromo-5-dodecylthiophene has also been presented in the synthesis of semiconducting calamitic and discotic liquid crystals, owing to the flexible long alkyl chain and the rigid thiophene/phenylene core.

General Information

CAS Number	153561-74-1
Chemical Formula	C₁₆H₂₇BrS
Full Name	2-Bromo-5-dodecylthiophene
Molecular Weight	311.35 g/mol
Synonyms	N/A
Classification / Family	Thiophene derivatives, Dyes, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	N/A
Boiling Point	T_b = 371.2±22.0 °C at 760 mmHg
Appearance	Yellow liquid

MSDS Documentation

2-Bromo-5-dodecylthiophene MSDS Sheet

Literature and Reviews

Asymmetric alkythienyl thienoacenes derived from anthra[2,3-b]thieno[2,3-d]thiophene for solution-processable organic semiconductors, Y. Ogawa et al., ACS Appl. Mater. Interfaces, 9, 9902−9909(2017); DOI: 10.1021/acsami.6b15793.
Bent-core mesogens with thiophene units, K. Geese et al., J. Mater. Chem., 20, 9658–9665(2010); DOI: 10.1039/C0JM01919D.
Influence of conjugation axis on the optical and electronic properties of aryl-substituted benzobisoxazoles, B. Tlach et al., J. Org. Chem., 78(13), 6570–6581(2013); DOI: 10.1021/jo4007927.
Near-infrared fluorescent thienothiadiazole dyes with large stokes shifts and high photostability, Y. Zhang et al., J. Org. Chem., 82(11), 5597–5606(2017);DOI: 10.1021/acs.joc.7b00422.
Small asymmetric anthracenethiophene compounds as organic thin-film transistors, B. Shaik et al., Tetrahedron, 69, 8191-8198(2013); DOI: 10.1016/j.tet.2013.07.041.
Two-dimensional nanostructures by the assembly of n-type tetraazaanthracene-based conjugated molecules, C. He et al., Chem. Phy. Chem., 14(13), 2954-2960(2013); DOI: 10.1002/cphc.201300444.

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