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P3HT Revisited – From Molecular Scale to Solar Cell Devices pp 1–38Cite as

Progress in the Synthesis of Poly (3-hexylthiophene)

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Part of the book series: Advances in Polymer Science ((POLYMER,volume 265))

Abstract

Polythiophene synthesis has undergone a multitude of changes, starting from the initial methods of acid-catalyzed polymerizations with low yields of oligomeric polythiophenes to modern methods using transition metal-based catalysts that allow controlled synthesis of poly(alkylthiophene)s with high molecular weight and regioregularity. The discovery of the opto-electronic properties of conjugated polymers played a major role in this development. Further improvements such as externally initiated polymerization not only enabled the synthesis of polymers that are almost 100% regioregular, but also gave the capability for in situ synthesis of these polymers on substrates, which increases their applicability in opto-electronic devices. This chapter summarizes developments in the methodology of polythiophene synthesis.

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Abbreviations

acac:

Acetylacetonate

Ar:

Aryl

Bn:

Benzyl

bpy:

2,2′-Bipyridyl

Bu:

Butyl

cat:

Catalyst

cod:

1,5-Cyclooctadiene

Cp:

Cyclopentadienyl

dppb:

Bis(diphenylphosphino)benzene

dppe:

Bis(diphenylphosphino)ethane

dppf:

Bis(diphenylphosphino)ferrocene

dppp:

Bis(diphenylphosphino)propane

Et:

Ethyl

HF:

Hydrofluoric acid

ITO:

Indium tin oxide

LDA:

Lithium diisopropylamide

Me:

Methyl

NBS:

N-Bromosuccinimide

NCS:

N-Chlorosuccinimide

P3AT:

Poly(3-alkylthiophene)

P3HT:

Poly(3-hexylthiophene)

P3MT:

Poly(3-methylthiophene)

PDI:

Polydispersity index

Ph:

Phenyl

PPh3 :

Triphenylphosphine

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

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    Prakash Sista & Christine K. Luscombe

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    Sabine Ludwigs

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Sista, P., Luscombe, C.K. (2014). Progress in the Synthesis of Poly (3-hexylthiophene). In: Ludwigs, S. (eds) P3HT Revisited – From Molecular Scale to Solar Cell Devices. Advances in Polymer Science, vol 265. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2014_278

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