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CAS Number 514188-72-8

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

Product Code B1521-LT-1g
Price $144 ex. VAT

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A popular alkylated thiophene building block

Adds solubility and thermal stability to the product molecules in application of OFETs and OPVs

2-Bromo-5-decylthiophene, derived from thiophene with a bromine and a decyl alkyl chain at 2- and 5- positions, is popularly used an end-capping reagent for the synthesis of semiconducting molecules including oligomers and polymers.

The bromine functional group provides the accessibility to a facile further functionalisation using Pd-catalysed cross-coupling or nucleophilic aromatic substitution reactions. The alkyl chain improves the solubility of the end product, also modifies the highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO-LUMO) energy levels. This thiophene derivative is an ideal candidate for synthesizing donor-acceptor-donor (D-A-D) type dye sensitizer for dye-sensitized solar cells (DSSCs).

2-bromo-5-decylthiophene building block, used as an end-capping precursor for thiophene/thiophene-phenylene type semiconducting oligomers, showed high charge mobilities up to 0.4 cm2/Vs. This alkylthiophene derivative with long flexible alkyl chain moiety is also suitable for preparing semiconducting liquid crystal materials.

General Information

CAS Number 514188-72-8
Chemical Formula C14H23BrS
Full Name 2-Bromo-5-decylthiophene
Molecular Weight 240.21 g/mol
Synonyms N/A
Relative Density 1.2±0.1 g/cm3
Classification / Family Thiophene derivatives, Dyes, End-capped, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics

Chemical Structure

2-Bromo-5-decylthiophene CAS 514188-72-8
2-Bromo-5-decylthiophene chemical structure, CAS 514188-72-8

Product Details

Purity N/A
Boiling Point Tb = 340.4±22.0 °C at 760 mmHg
Appearance Yellow liquid

MSDS Documentation

2-Bromo-5-decylthiophene2-Bromo-5-decylthiophene MSDS Sheet

Literature and Reviews

  1. Synthesis and thermal behaviour of α,α′-didecyloligothiophenes, S. Ponomarenko et al., J. Mater. Chem., 13, 197-202 (2003); DOI: 10.1039/b209176c.
  2. Synthesis and Physicochemical Properties of Piceno[4,3‑b:9,10‑b′]dithiophene Derivatives and Their Application in Organic Field-Effect Transistors, K. Hyodo et al., ACS Omega, 2, 308−315(2017); DOI: 10.1021/acsomega.7b00015.
  3. End-capping groups for small-molecule organic semiconducting materials: synthetic investigation and photovoltaic applications through direct C-H (hetero)arylations, T.-J. Lu et al., Eur. J. Org. Chem., 2017(1), 111-123(2016); DOI: 10.1002/ejoc.201601257.
  4. Decyl-end-capped thiophene-phenylene oligomers as orgniac semiconducting materials with improved oxidation stability, S. Ponomarenko et al., Chem. Mater., 18, 579-586(2006); DOI: 10.1021/cm052210m.
  5. Conformationally twisted semiconducting polythiophene derivatives with alkylthiophene side chain: high solubility and air stability, J. Park, Macromolecules, 43, 2118–2123 (2010); DOI: 10.1021/ma902396n.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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