5,5′′-Dibromo-2,2′:5′,2′′-terthiophene

CAS Number 98057-08-0

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

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene

This intermediate is widely used for the synthesis of semiconducting molecules, oligomers and conjugated polymers.

Specifications | MSDS | Literature and Reviews

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene (CAS number 98057-08-0) is a brominated derivative of α-terthienyl at 5,5′′-positions. 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene can be prepared via bromination with N-Bromosuccinimide in N,N-dimethylformamide (DMF).

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene is a useful building block for the further synthesis of small molecules, oligomers and conjugated semiconducting polymers. Pyrene end-capped thiophene oligomer 5,5′′-di(pyren-1-yl)-2,2′:5′,2′′-terthiophene prepared from one step synthesis from 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene show great potential as semiconducting materials for OTFTs and OSCs. Devices based on 5,5′′-di(pyren-1-yl)-2,2′:5′,2′′-terthiophene exhibited a field effect mobility of 0.11 cm2 V−1 s−1. Naphthyl end-capped oligothiophenes are also good candidates for high-performance organic electronic devices. Methoxy-functionalized 5,5′′-bis-(6-methoxynaphth-2-yl)-2:2′,5′:2′′-terthiophene (MONaT3) substantially increases the crystallization into aligned fibers.

General Information

CAS Number	98057-08-0
Chemical Formula	C₁₂H₆Br₂S₃
Full Name	5,5′′-Dibromo-2,2′:5′,2′′-terthiophene
Molecular Weight	406.18 g/mol
Synonyms	2,5-Bis(5-bromothiophen-2-yl)thiophene
Classification / Family	Terthiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR in CDCl₃)
Melting Point	158.0 °C
Appearance	Light yellow powder/crystals

MSDS Documentation

5,5′′-Dibromo-2,2′:5′,2′′-terthiophene MSDS Sheet

Literature and Reviews

Selective Synthesis of α-Substituted Oligothiophenes, P. Bauerle, et al., Synthesis,11, 1099-1103 (1993); DOI:10.1055/s-1993-26009.
Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5′-Bis(dicyanomethylene)-5,5′-dihydro-Δ2,2′-bithiophene and Related Compounds, Y. Koji et al., Bull. Chem. Soc. Jpn., 62 (5), 1539-1546 (1989); DOI: 10.1246/bcsj.62.1539.
Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives, P. Liu et al., Tetrahedron 60 (24), 5259-5264 (2004); DOI: 10.1016/j.tet.2004.04.029.

Two-photon induced emissive thiophene donor–acceptor systems as molecular probes for in vitro bio-imaging: synthesis, crystal structure, and spectroscopic properties, C. Chow, RSC Adv., 3, 18835-18843 (2013); DOI: 10.1039/C3RA42914H.
Conformation modification of terthiophene during the on-surface synthesis of pure polythiophene, L. Liu et al., Nanoscale, 12, 18096-18105 (2020); DOI: 10.1039/D0NR04529B.
Substrate steered crystallization of naphthyl end-capped oligothiophenes into nanofibers: the influence of methoxy-functionalization, F. Balzer et al., Phys. Chem. Chem. Phys., 16, 5747-5754 (2014); DOI: 10.1039/C3CP53881H.
Pyrene end-capped oligothiophene derivatives for organic thin-film transistors and organic solar cells, J. Kwon et al., New J. Chem., 36, 1813-1818 (2012); DOI: 10.1039/C2NJ40348J.
A novel method for the bromination of thiophenes, P. Arsenyan et al., Tetrahedron Lett., 51, 205–208 (2010); DOI: 10.1016/j.tetlet.2009.10.133.
Synthesis and Characterization of Diperfluorooctyl-Substituted Phenylene-Thiophene Oligomers as n-Type Semiconductors. Molecular Structure-Film Microstructure-Mobility Relationships, Organic Field-Effect Transistors, and Transistor Nonvolatile Memory Elements, A. Facchetti et al., Chem. Mater., 16, 4715-4727 (2004); DOI: 10.1021/cm0495008.