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2-Bromo-5-decylthiophene 

CAS Number 514188-72-8

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

2-Bromo-5-decylthiophene  CAS 514188-72-8
Product Code B1521-LT-1g
Price £115 ex. VAT
£ GBP

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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 (CAS number 514188-72-8), 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.
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