5,5'-Dibromo-4,4'-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, g344-BTBr, CAS 1404493-47-5
Specifications | MSDS | Literature and Reviews
g344-BTBr, 5,5'-dibromo-4,4'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene, has a bithiophene backbone with glycol side chains at 4,4'-positions. The glycol side chains on the thiophene backbone help for high currents, transconductance, and sharp subthreshold switching while maintaining fast switching speeds in accumulation mode organic electrochemical transistors (OECTs) . 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.
g344-BTBr is the isomer of 5,5'-dibromo-3,3'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene (g333-BTBr). The planarizing effects of the S–O interactions are redistributed along the backbone by the positioning change of the side chains, t, resulting planar structure. With improved planarity, pgBTTT, derived from g344-BTBr, demonstrated higher hole mobility (μ) of 3.44 ± 0.13 cm2 V–1 s–1, comparing to 0.41 ± 0.13 cm2 V–1 s–1 of p(g2T-TT). derived from g333-BTBr. PEGylation has been a common technique in pharmaceutical applications with better compatibility and electrochemically doped EG-functionalized materials are exceeding the performance of PEDOT:PSS in OECTs.
General Information
| CAS Number | 1404493-47-5 |
| Chemical Formula | C22H32Br2O8S2 |
| Full Name | 5,5'-Dibromo-4,4'-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2'-bithiophene |
| Molecular Weight | 648.42 g/mol |
| Synonyms | g344-BTBr, 2,2'-Bithiophene, 5,5'-dibromo-4,4'-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]- |
| Classification / Family | Bithiophenes, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics |
Chemical Structure
Product Details
| Purity | >98% (HPLC) |
| Melting Point | N/A |
| Appearance | Dark green solid |
MSDS Documentation
g344-BTBr MSDS SheetLiterature and Reviews
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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.
- S. Moro et al. (2022); The Effect of Glycol Side Chains on the Assembly and Microstructure of Conjugated Polymers, ACS Nano, 16 (12), 21303-21314; DOI: 10.1021/acsnano.2c09464.