Regiochemistry of Poly(3-hexylthiophene): Synthesis and Investigation of a Conducting Polymer

Pappenfus, Ted M.; Hermanson, David; Kohl, Stuart G.; Melby, Jacob H.; Thoma, Laura M.; Carpenter, Nancy E.; Filho, Demétrio A. da Silva; Brédas, Jean Luc

doi:10.1021/ed800144p

Cited by 23 publications

(20 citation statements)

References 27 publications

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“…The blue shift which is in turn obtained in case of regiorandom pattern causes decrease in the conjugation. This decrease comes from the twisting of the thiophene ring and from the lower number of π-π stacking interactions along the polymers (Barta et al, 1999;Cutler, 2000;Mccullough et al, 1993;Pappenfus et al, 2010).…”

Section: Spectral Analysis Of 3ht-containing Irradiated Solutionsmentioning

confidence: 99%

Radiation-induced polymerization of 3-hexylthiophene in oxygen-free and oxygen-saturated dichloromethane solvent

Bahry

Cui

Dazzi

et al. 2021

Radiation Physics and Chemistry

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As alternative radiolytic approach, the synthesis of P3HT was made possible thanks to the oxidation of 3HT monomers by chloromethyl and dichloromethyl radicals or by their corresponding peroxyl radicals in situ produced by dichloromethane solvent radiolysis. Under two different experimental conditions, in oxygen-free solution and in oxygen-saturated solution, two different polymers, "P3HT N2 " and "P3HT O2 " respectively, were successfully synthesized. Both produced materials were discerned by several analytical and spectroscopic techniques. UV-Vis absorption spectroscopy results showed that the radiolytic yield of 3HT oxidation in dichloromethane solvent is higher under O 2 atmosphere. Indeed, a dose of 75 kGy was needed to polymerize 10 mM in 3HT under N 2 atmosphere, meanwhile a dose of 35 kGy was sufficient to polymerize the same amount of 3HT under O 2 . The average molecular weight of P3HT O2 was found higher than that of P3HT N2 as revealed by SEC chromatography analysis. Also, P3HT O2 exhibits better thermal stability than P3HT N2 . ATR-FTIR spectroscopy revealed the specific presence into P3HT O2 polymers of some functional groups such as carbonyl, hydroxyl and carboxyl moieties, which clearly explains the difference between the morphological structures of P3HT N2 and P3HT O2 as highlighted by cryo-TEM, SEM and AFM microscopies. Finally, both radio-synthesized P3HT N2 and P3HT O2 polymers were found characterized by remarkably significant conductive, electronic and optical properties.

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Section: Spectral Analysis Of 3ht-containing Irradiated Solutionsmentioning

confidence: 99%

Radiation-induced polymerization of 3-hexylthiophene in oxygen-free and oxygen-saturated dichloromethane solvent

Bahry

Cui

Dazzi

et al. 2021

Radiation Physics and Chemistry

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“…Organic solar cells are fabricated as an activity in our two-credit laboratory course, Introduction to Research (ItR), which has been previously described in this Journal . The introduction of organic solar cells complements well our previously reported experiment on the synthesis and characterization of a conducting polymer which is also performed by the second year chemistry and biochemistry majors in the ItR course. The main learning objectives for the solar cell fabrication component of the course are for students to learn about the basic components of the cells, their construction, and their fundamental working mechanism for power generation.…”

Section: Resultsmentioning

confidence: 73%

“…While undergraduate laboratory experiments exist for the fabrication and characterization of perovskite solar cells, , silicon solar cells, and dye sensitized solar cells, , and for the synthesis of conducting polymers for organic solar cells, few reports exist for the fabrication and characterization of organic solar cells. Current academic and industry solar cell fabrication protocols are not well-suited for adaptation to undergraduate or school teaching laboratories, because they require access to expensive, highly technical equipment, but we have distilled current state-of-the-art organic electronic technology into an easily accessible kit for a teaching laboratory.…”

Section: Introductionmentioning

confidence: 99%

Developing a Portable Organic Solar Cell Kit Suitable for Students to Fabricate and Test Solar Cells in the Laboratory

et al. 2020

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An organic solar cell fabrication kit has been developed for demonstration in both undergraduate teaching classes and high school laboratories to promote the growing field of renewable energy and to facilitate empirical comprehension of solar technology. The laboratory focuses on fabricating organic photovoltaics (solar cells) and testing the efficiency of power generation. By restricting substances to nontoxic coating inks, and a Pb-free alloy for the cathode, chemical hazards are minimized. Usually, organic solar cell fabrication requires the use of expensive laboratory equipment only found in a university or an industry environment, such as fume hoods, large spin coaters, nitrogen glove boxes, and metal evaporation systems. Importantly, the solar cell kit has been specifically developed to remove the need for accessing this large and expensive equipment: nontoxic inks are used such that fume hoods are not necessary, a portable miniature spin coater has been developed such that large spin coaters with a vacuum connection are not required, and a low-melting-point (62 °C) Pb-free alloy has been trialed such that access to high-vacuum metal evaporation equipment is not necessary. The exercise utilizes a pedagogical framework of preliminary predictive exercises, practical verification of device optimization and engineering to illuminate the key working principles of a solar cell, and a post-exercise quiz to provide feedback and assess embedded knowledge. This experiment is an introductory lesson in renewable energy and gives students exposure to the chemistry, physics, and materials science concepts of organic electronics.

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“…1 H NMR and UV–vis are both useful for analyzing P3HT regiochemistry with 1 H NMR providing additional insight into the polymer structure such as β‐branching. Although both aromatic and aliphatic 1 H NMR signals of P3HT provide valuable insight, we limited our analysis for this study to aliphatic protons for determining amounts of head‐to‐tail (HT) couplings at 2.82 ppm, head‐to‐head (HH) couplings at 2.57 ppm, and β‐branching in the 2.18–2.38 ppm region as outlined previously in the literature .…”

Section: Resultsmentioning

confidence: 99%

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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Regiochemistry of Poly(3-hexylthiophene): Synthesis and Investigation of a Conducting Polymer

Cited by 23 publications

References 27 publications

Radiation-induced polymerization of 3-hexylthiophene in oxygen-free and oxygen-saturated dichloromethane solvent

Radiation-induced polymerization of 3-hexylthiophene in oxygen-free and oxygen-saturated dichloromethane solvent

Developing a Portable Organic Solar Cell Kit Suitable for Students to Fabricate and Test Solar Cells in the Laboratory

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

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