5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene

CAS Number 1974310-58-1

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

5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene

A bithiophene derivative bearing glycol side chains for the synthesis of semiconducting oligomers, polymers in application of OFETs and OSCs.

Specifications | MSDS | Literature and Reviews

5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene, CAS number 1974310-58-1, has a bithiophene backbone with glycolated side chains at 3,3-positions which are there to enhance hydrophilicity and promote solubility of desired structures. Two bromo functional groups at 5,5'-positions enable the structure to extend its conjugation to form oligomeric and polymeric semiconductors. The oxygen atoms in the side chains can also promote intramolecular S--O interactions of the head-to-head coupled bithiophene units to induce backbone coplanarity and increase the effective conjugation length of the polymer chains for efficient charge transport in film state.

5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene is used for the synthesis of poly(2-(3,3′-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-[2,2’-bithiophen]-5-yl)thieno[3,2-b]thiophene), p(g2T-TT). The glycolated side chains on the thiophene backbone is believed to result with high currents, transconductance, and sharp subthreshold switching while maintaining fast switching speeds in accumulation mode organic electrochemical transistors (OECTs) .

General Information

CAS Number	1974310-58-1
Chemical Formula	C₂₂H₃₂Br₂O₈S₂
Full Name	5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene
Molecular Weight	648.42 g/mol
Synonyms	g333-BTBr, 2,2'-Bithiophene, 5,5'-dibromo-3,3'-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-
Classification / Family	Bithiophenes, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

1974310-58-1 - 5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene — 5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene chemical structure, CAS 1974310-58-1

Product Details

Purity	>98% (HPLC)
Melting Point	N/A
Appearance	Off-white to yellowish powder/crystals

MSDS Documentation

5,5'-Dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene MSDS Sheet

Pricing

Batch	Quantity	Price
B1121-500mg	500 mg	£240
B1121-1g	1 g	£380
B1121-5g	5 g	£1550

Literature and Reviews

Controlling the mode of operation of organictransistors through side-chain engineering, A. Giovannitt et al., PNAS, 113 (43) 12017-12022; DOI: 10.1073/pnas.1608780113.
A universal and facile approach for building multifunctional conjugated polymers for human-integrated electronics, N. Li et al., Matter 4, 3015–3029 (2021); DOI: 10.1016/j.matt.2021.07.013.
Role of the Anion on the Transport and Structure of Organic Mixed Conductors, C. Cendra et al.,Adv. Funct. Mater., 29 (5), 1807034 (2019); DOI: 10.1002/adfm.201807034.

A Low-Swelling Polymeric Mixed Conductor Operating in Aqueous Electrolytes, T. Nicolini et al., Adv. Mater., 33 (2), 2005723 (2020); DOI: 10.1002/adma.202005723.
Conjugated Polymers for Microwave Applications: Untethered Sensing Platforms and Multifunctional Devices, S. Tan et al., Adv. Mater., 34, 2202994 (2022); DOI: 10.1002/adma.202202994.
Propylene and Butylene Glycol: New Alternatives to Ethylene Glycol in Conjugated Polymers for Bioelectronic Applications, M. Moser et al., Mater. Horiz., 9, 973-980 (2022); DOI: 10.1039/D1MH01889B.
Regiochemistry-driven Organic Electrochemical Transistor Performance Enhancement in Ethylene Glycol Functionalized Polythiophenes, R. Hallani et al., J. Am. Chem. Soc., 143, 29, 11007–11018 (2021); DOI: 10.1021/jacs.1c03516..