5,5'-Dibromo-4,4'-dihexyl-2,2'-bithiophene

CAS Number 214493-03-5

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Monomers

5,5'-Dibromo-4,4'-dihexyl-2,2'-bithiophene MSDS

5,5'-Dibromo-4,4'-dihexyl-2,2'-bithiophene CAS 214493-03-5

An alkylated bithiophene building block with two bromo-functional groups

A bithiophene derivatives for semiconducting oligomer/polymer synthesis in application of OFETs and OSCs

Overview
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5,5'-Dibromo-4,4'-dihexyl-2,2'-bithiophene (CAS number 214493-03-5) is a derivative of bithiophene with two hexyl groups at 4,4'-positions and two bromine group at 5,5'-positions, allowing further functionalization as well as gaining excellent solubility. It is facile for synthesising thiophene oligomer/polymer and block copolymer/small molecules with other building blocks such as perylene, triphenylamine and carbazoles.

5,5'-Dibromo-4,4'-dihexyl-2,2'-bithiophene has a well-defined structure with two thiophene units joined at 2,2'-positions and two hexyl groups being away from each other at 4,4'-positions. This is particularly useful when certain desired structure conformation to be achieved or film morphology issues to be addressed, unlike the random coupling reactions between mono-thiophenes.

General Information

CAS Number	214493-03-5
Chemical Formula	C₂₀H₂₈Br₂S₂
Full Name	5,5'-dibromo-4,4'-dihexyl-2,2'-bithiophene
Molecular Weight	492.37 g/mol
Synonyms	2-bromo-5-(5-bromo-4-hexylthiophen-2-yl)-3-hexylthiophene
Classification / Family	thiophene derivatives, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Boiling Point	T_b > 468.8±40.0 °C at 760 mmHg
Appearance	Yellow liquid
Relative density	1.4±0.1 g/cm³

MSDS Documentation

5,5'-Dibromo-4,4'-dihexyl-2,2'-bithiophene MSDS Sheet

Literature and Reviews

Thiophene in conducting polymers: synthesis of poly(thiophene)s and other conjugated polymers containing thiophenes, for application in polymer solar cell, F. Livi et al., Top. Heterocycl. Chem., 39, 203–226(2015); DOI: 10.1007/7081_2014_128.
Nanoscale correlation between exciton dissociation and carrier transport in silole-containing cyclopentadithiophene-based bulk heterojunction films, J.-H. Huang et al., J. Phys. Chem. C, 115, 2398–2405(2011); DOI: 10.1021/jp1090894.
Polymer for electronics and spintronics, P. Bujak et al., Chem. Soc. Rev., 42, 8895–8999(2013); DOI: 10.1039/c3cs60257e.
Pyrrole-containing semiconducting materials: synthesis and applications in organic photovoltaics and organic field-effect transistors, C. Bulumulla et al., ACS Appl. Mater. Interfaces, 12, 32209−32232(2020); DOI: 10.1021/acsami.0c07161.
Rod-like oligomers incorporating 2,6-dialkylamino core-substituted naphthalene diimide as acceptors for organic photovoltaic, R. Fernando et al., Org. Electron., 14, 1683–1692(2013); DOI:10.1016/j.orgel.2013.03.039.
Small molecules based on bithiazole for solution-processed organic solar cells, Y. Lin et al., Org. Electron., 13, 673-680(2013); DOI: 10.1016/j.orgel.2012.01.016.
Synthesis and applications of 2,7-carbazole-based conjugated main-chain copolymers containing electron deficient bithiazole units for organic solar cells, D. Patra et al., J. Polym. Sci. A Polym. Chem., 48, 5479-5489(2010); DOI: 10.1002/pola.24356.
Synthesis and characterization of soluble low-bandgap oligothiophene-[all]-S,S-dioxides-based conjugated oligomers and polymers, E. Amir et al., J. Polym. Sci. A Polym. Chem., 49, 1933-1941 (2011); DOI: 10.1002/pola.24641.
Synthesis and photovoltaic properties of low bandgap dimeric perylene diimide based non-fullerene acceptors, X. Zhang et al., Sci. China Chem., 59, 209–217 (2016); DOI: 10.1007/s11426-015-5485-8

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