Design of Soluble Hyperbranched Polythiophenes with Tailor‐Made Optoelectronic Properties

Richter, T.; Link, Steffen; Hanselmann, Ralf; Ludwigs, Sabine

doi:10.1002/marc.200900186

Cited by 30 publications

(50 citation statements)

References 34 publications

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“…T8 3 structure differs from the “swivel cruciform” α‐terthiophene dimer ( BT3 ), a p ‐type semiconductor investigated by Scherf, for the presence of the 2‐thienyl units in position ortho to the bond containing the stereogenic axis responsible for the atropisomerism . They also formally result from doubling the 5′‐(2‐thienyl)‐2,2′,3′,2“‐terthiophene ( 4 T ), a monomer widely used by Ludwigs for preparing hyperbranched polythiophenes by electrochemical or chemical oxidation –. This monomer is also the constitutional isomer of the T′8 4 , a member of the class of the spider‐like oligothiophenes cited above (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Inherently Chiral Spider‐Like Oligothiophenes

Sannicolò

Mussini

Benincori

et al. 2016

Chemistry A European J

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The racemate of an inherently chiral "spider-like" octathiophene monomer T83 , in which chirality is generated by torsion in its backbone, was synthesized. The racemate was resolved into configurationally stable antipodes by HPLC on a chiral stationary phase. Electrooxidation of the enantiomers resulted in materials displaying high enantiorecognition ability towards the antipodes of some chiral probes. Moreover, the T83 racemate demonstrated great aptitude to stimulate formation of 3D rigid architectures if used as a cross-linking monomer for molecular imprinting. This feature was exploited to devise a molecularly imprinted polymer-based chemosensor selective for a thymine-adenine oligonucleotide.

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Section: Resultsmentioning

confidence: 99%

Inherently Chiral Spider‐Like Oligothiophenes

Sannicolò

Mussini

Benincori

et al. 2016

Chemistry A European J

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“…15 Acetonitrile (hypergrade) was purchased from Merck and used as received. Tetrabutylammonium hexafluorophosphate (puriss.)…”

Section: Experimental Methodsmentioning

confidence: 99%

Electrochemical Behavior of Electropolymerized and Chemically Synthesized Hyperbranched Polythiophenes

et al. 2010

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Hyperbranched polythiophenes were synthesized by potentiodynamic electropolymerization of 2,2';3',2''-terthiophene and 5'-(2-thienyl)-2,2';3',2''-terthiophene. The molecular architecture, i.e., the extent of branching of the resulting polymers, could be adjusted by varying the switching potentials. We compare these systems to hyperbranched polythiophenes which we obtained via a simple one-pot synthesis route based on FeCl(3) oxidative polymerization of the monomers. Interestingly, we find that the properties of the electropolymerized materials obtained with high switching potentials are comparable to those of the chemically synthesized polythiophenes. A detailed optical and electrochemical characterization of these systems is performed showing the high potential of this material class for optoelectronic applications. Cyclic voltammetry coupled with in situ conductance measurements further reveal reversible doping upon oxidation (p-doping) and reduction (n-doping) and comparable values for the conductance for the chemically and electrochemically synthesized materials.

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“…they are simply called branching defects. Although the influence of branching on conjugated polythiophenes has been studied previously, the monomers either did not contain alkyl chains or β,β‐linkages instead of α,β‐linkages were studied making the direct comparison with DArP‐produced β‐defects difficult.…”

Section: Structural Defects In Darp Polymersmentioning

confidence: 99%

Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure

Rudenko

Thompson

2014

J. Polym. Sci. Part A: Polym. Chem.

193

224

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As a newly emerged protocol for the synthesis of conjugated polymers, direct arylation polymerization (DArP) is an environmentally friendly and cost-effective alternative to traditional methods of polymerization. DArP efficiently yields conjugated polymers with high yield and high molecular weight. However, DArP is also known to produce defects in polymer chemical structure. Together with molecular weight and polydispersity, these defects are considered to be important parameters of polymer structure and they have a strong impact on optical, electronic and thermal properties of conjugated polymers. The four major classes of conjugated polymer defects inherent for DArP have been identified: homocoupling regiodefects, branching defects, end group defects, and residual metal defects. To have a precise control over the polymer properties, it is important to understand what causes the defects to form during the polymerization process and be able to control their content. Here within the scope of current literature, we discuss in detail the definition and origin of all these defects, their influence on polymer properties and effective means to control the defects through fine tuning of the DArP reaction parameters.

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Design of Soluble Hyperbranched Polythiophenes with Tailor‐Made Optoelectronic Properties

Cited by 30 publications

References 34 publications

Inherently Chiral Spider‐Like Oligothiophenes

Inherently Chiral Spider‐Like Oligothiophenes

Electrochemical Behavior of Electropolymerized and Chemically Synthesized Hyperbranched Polythiophenes

Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure

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