3-Hexylthiophene

Order Code: B301
MSDS sheet

Price

(excluding Taxes)

£139.00


General Information

CAS number
1693-86-3
Chemical formula C10H16S
Molecular weight 168.30 g/mol
Synonyms 1-(Thien-3-yl)hexane
3-n-Hexylthiophene
Classification / Family

Monomers, Building blocks, Thiophene, heterocycles, Chemical synthesis for low band gap polymers

Intermediates for OFETs, OLED, Organic Photovoltaics, Polymer Solar Cells

Product Details

Purity

99%

Boiling point

65°C at 0.45 mmHg (lit.)

299°C at 760 mmHg (1 atm, lit.)

Density

0.936 g/cm3

Colourless/pale yellow liquid

Chemical Structure

 
Chemical structure of 3-Hexylthiophene
CAS number 1693-86-3; Chemical formula C10H18S

Applications

3-Hexylthiophene is the intermediate for the synthesis of poly(3-hexylthiophene), referred as P3HT, which is, to date, the most studied polymer for polymer solar cells. The efficiency of a P3HT/PCBM solar cell is typically 4-5 %, but with new fullerene materials developed to closely match the energy levels of P3HT (HOMO 5.0 eV, LUMO 3.0 eV), device performance have pushed to 6.5% [1].

The synthesis of P3HT is relatively easy and short, only a 3-4 step synthesis is required [2, 3, 4]. The challenge of P3HT is that it only absorbs a narrow band of solar spectrum hence the room to improve its performance efficiency is quite limited.

 P3HT synthesis
 
Synthesis of HT-coupled, regioregular poly(3-dodecylthiophene)

NMR Characterisation

 

1H NMR 3-hexylthiophene in CDCl3
1H NMR spectrum of 3-hexylthiophene in CDCl3: Instrument AVIIIHD400 (view full version)

Literature and Reviews

  1. 6.5% Efficiency of Polymer Solar Cells Based on poly(3‐hexylthiophene) and Indene‐C60 Bisadduct by Device Optimization, G. Zhao et al., Adv. Mater., 22, 4355–4358 (2010).
  2. Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties, Chen et. al., J. Am. Chem. Soc., 117 (1), pp 233–244 (1995).
  3. A Simple Method to Prepare Head-to-Tail Coupled, Regioregular Poly(3-alkylthiophenes) Using Grignard Metathesis., R. S. Loewe et al., Adv. Mater., 11: 250–253 (1999)
  4. Synthesis and characterisation of telechelic regioregular head-to-tail poly(3-alkylthiophenes), A. Iraqi et. al., J. Mater. Chem., 8, 25-29 (1998).
  5. Charge Transport and Photocurrent Generation in Poly(3-hexylthiophene):Methanofullerene Bulk-Heterojunction Solar Cells, D. Valentin et al, Adv. Funct. Mater., 16, 699–708 (2006).
  6. Soluble and processable regioregular poly(3‐hexylthiophene) for thin film field‐effect transistor applications with high mobility, Z. Bao et al., Appl. Phys. Lett. 69, 4108 (1996).
  7. Dependence of Regioregular Poly(3-hexylthiophene) Film Morphology and Field-Effect Mobility on Molecular Weight, R. J. Kline, Macromolecules, 38 (8), pp 3312–3319 (2005).