3,3'-Dibromo-2,2'-bithiophene

CAS Number 51751-44-1

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

3,3'-Dibromo-2,2'-bithiophene CAS 51751-44-1

3,3'-Dibromo-2,2'-bithiophene available to buy online

Key intermediate for the preparation of semiconducting molecules, oligothiophenes and polymers

Overview
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3,3'-Dibromo-2,2'-bithiophene (CAS number 51751-44-1) is an isomer to 5,5'-Dibromo-2,2'-bithiophene. It is a key intermediate for the preparation of semiconducting molecules, oligothiophenes and polymers which find applications in a variety of organic electronic and optoelectronic devices. These include organic field-effect transistors, chemical sensors, and organic solar cells.

Alkylation or arylation at 3-positions of the bithiophene not only provide either extended conjugation or improved solubility, but also give new functionality to change the electron and photophysical properties of the target materials. In addition, alkylation or arylation at 3-positions has a significant impact on the crystallinity of the target molecules to tune the morphology and the microstructure of the cast films.

Substitution of the bromines with either fluorine (F) or cyano (CN) groups makes the structure more electron deficient, which has a pounding effect on the device performance in terms of charge mobility, stability and overall OFET and OPV device efficiency.

3,3'-Dibromo-2,2'-bithiophene is also a must have building block for the synthesis of more complicated fused structures such as dithieno[3,2-b:2,3-d]pyrroles (DTP), dithieno[3,2-b:2,3-d]silole (DTS), dithieno[3,2-b:2,3-d]selenophene (DTSe), dithieno[3,2-b:2′,3′-d]germole (DTG) and 4,4′-Spiro-bis[cyclopenta[2,1-b;3,4-b′]dithiophene] (SCT).

General Information

CAS Number	51751-44-1
Chemical Formula	C₈H₄Br₂S₂
Full Name	3,3'-Dibromo-2,2'-bithiophene
Molecular Weight	324.06 g/mol
Synonyms	2,2'-Bi(3-bromothiophene)
Classification / Family	Bithiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR in CDCl₃)
Melting Point	99 °C
Appearance	White-yellowish powder

MSDS Documentation

3,3'-Dibromo-2,2'-bithiophene MSDS Sheet

Literature and Reviews

Simplified Synthetic Approach to Tetrabrominated Spiro-Cyclopentadithiophene and the Following Derivation to A-D-A Type Acceptor Molecules for Use in Polymer Solar Cells, X. Liu et al., J. Org. Chem., 87 (8), 5057–5064 (2022).
Polymerization of Solid-State 2,2′-Bithiophene Thin Film or Doped in Cellulose Paper Using DBD Plasma and Its Applications in Paper-Based Electronics, K. Chen et al., ACS Appl. Polym. Mater., 2 (4), 1518–1527 (2020); DOI: 10.1021/acsapm.9b01202.
Design of novel electroactive polybithiophene derivatives, K. Faid et al., Macromolecules, 26 (10), 2501–2507 (1993); DOI: 10.1021/ma00062a017.
Synthesis and properties of novel bis(triarylamines) based on a 3,3'-diphenyl-2,2'-bithiophene core, K. Wong et al., Chem. Commun., 1628–1629 (2001); DOI: 10.1039/b103194p.
Improved Synthesis of N-alkyl Substituted Dithieno[3,2-b:2’,3’-d]pyrroles, G. Koeckelberghs et al., Tetrahedron, 61 (3), 687-691 (2005); DOI: 10.1016/j.tet.2004.10.106.
Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3%, T. Chu et al., J. Am. Chem. Soc., 133 (12), 4250–4253 (2011); DOI: 10.1021/ja200314m.

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