2-Bromo-5-decylthiophene

CAS Number 514188-72-8

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

2-Bromo-5-decylthiophene CAS 514188-72-8

A popular alkylated thiophene building block

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

Specifications | MSDS | Literature and Reviews

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.

Thiophene building block

for the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Capped with bromides

for facile coupling reactions

High purity

>98% Purity

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

Product Details

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

MSDS Documentation

2-Bromo-5-decylthiophene MSDS Sheet

Literature and Reviews

Synthesis and thermal behaviour of α,α′-didecyloligothiophenes, S. Ponomarenko et al., J. Mater. Chem., 13, 197-202 (2003); DOI: 10.1039/b209176c.
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.
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.

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.
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.