Benzodithiophene homopolymers via direct (hetero)arylation polymerization

Cicha, Calvin L.; Gockel, Samuel N.; Helmin, Andrew J.; Wilcox, Wyatt D.; Janzen, Daron E.; Pappenfus, Ted M.

doi:10.1007/s00289-018-2346-6

Cited by 5 publications

(2 citation statements)

References 28 publications

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“…The reaction conditions for P5 were further investigated by replacing the phosphine ligand P( o ‐OMePh) 3 with P( o ‐NMe 2 Ph) 3 at the 2.5 g scale (entry P6 ). While P( o ‐OMePh) 3 has been shown to work well for some DArP reactions, [39.42] it is outperformed by P( o ‐NMe 2 Ph) 3 in many instances—including our current investigation. This substitution not only increased the reaction yield and molecular weight, but also resulted in a polymer with greater regioregularity as shown by 1 H NMR and UV–vis spectroscopy.…”

Section: Resultsmentioning

confidence: 80%

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale‐Up, Solar Cell Performance, and Cost Analyses

Pappenfus

Almyahi

Cooling

et al. 2018

Macro Chemistry & Physics

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This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3‐hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2‐methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β‐defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large‐scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.

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Section: Resultsmentioning

confidence: 80%

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale‐Up, Solar Cell Performance, and Cost Analyses

Pappenfus

Almyahi

Cooling

et al. 2018

Macro Chemistry & Physics

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“…Despite its many interesting merits, the method has a drawback: its selectivity between C–H bonds for some monomers is poor. Consequently, the method is more commonly used to synthesize homopolymers like poly-3-hexylthiophene (P3HT) and benzodithiophene (BDT) [ 4 , 5 , 6 ]. However, D–A copolymers synthesized by DAP method are limited.…”

Section: Introductionmentioning

confidence: 99%

Photophysical, Thermal and Structural Properties of Thiophene and Benzodithiophene-Based Copolymers Synthesized by Direct Arylation Polycondensation Method

2021

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Three low-band-gap copolymers based on isoindigo acceptor units were designed and successfully synthesized by direct arylation polycondensation method. Two of them were benzodithiophene (BDT)-isoindigo copolymers (PBDTI-OD and PBDTI-DT) with 2-octlydodecyl (OD) and 2-decyltetradecyl (DT) substituted isoindigo units, respectively. Thiophene donor and DT-substituted isoindigo acceptor units were copolymerized to synthesize PTI-DT. The copolymers have a broad absorption range that extends to over 760 nm with a band gap ≈1.5 eV. The photophysical property studies showed that the BDT-based copolymers have non-polar ground states. Their emission exhibited the population of the intramolecular charge transfer (ICT) state in polar solvents and tightly bound excitonic state in non-polar solvents due to self-aggregation. On the contrary, the emission from the thiophene-based copolymers was only from the tightly bound excitonic state. The thermal decomposition temperature of the copolymers was above 380 °C. The X-ray diffraction pattern of the three copolymers showed a halo due to π−π stacking. A second, sharper peak was observed in the BDT-based copolymer with a longer side chain on the isoindigo unit (PBDTI-DT), and the thiophene-based copolymers with PTI-DT, exhibiting a better structural order.

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Structures, properties and application of benzodithiophene derivatives: A review

Wei,

Peng,

Zhong

et al. 2024

Dyes and Pigments

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Benzodithiophene homopolymers via direct (hetero)arylation polymerization

Cited by 5 publications

References 28 publications

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale‐Up, Solar Cell Performance, and Cost Analyses

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale‐Up, Solar Cell Performance, and Cost Analyses

Photophysical, Thermal and Structural Properties of Thiophene and Benzodithiophene-Based Copolymers Synthesized by Direct Arylation Polycondensation Method

Structures, properties and application of benzodithiophene derivatives: A review

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