Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

Marzano, Giuseppina; Ciasca, C. V.; Babudri, Francesco; Bianchi, Gabriele; Pellegrino, Andrea; Pò, Riccardo; Farinola, Gianluca M.

doi:10.1002/ejoc.201402226

Cited by 68 publications

(70 citation statements)

References 217 publications

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“…The ROMP of conjugated double bonds that contain cyclopolyenes is a remarkable method for the synthesis of conductive polymers for optoelectronics (Scheme ) …”

Section: Representative Examples Of the Conversion And Synthesis Of Cmentioning

confidence: 99%

Ruthenium‐Catalyzed Metathesis of Conjugated Polyenes

et al. 2016

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Abstract:In the past decade numerous examples of olefin metathesis-based chemical technologies have been developed making olefin metathesis increasingly dominant in several sustainable and green chemical processes. In spite of the wide application profile, conjugated olefin metathesis -especially conjugated polyene metathesis -is an area of great interest with little exploration. Metathesis of conjugated polyenes is often cumbersome and requires high catalyst loading, most probably due to formation of less or inactive ruthenium  3 -vinylcarbene intermediates. Mechanistic understanding and development of a new highly active catalytic system for olefin metathesis will open new areas for exploration. For example, the utilization of petrochemical by products such as cyclopentadiene or a new way in utilizing butadiene, isoprene and conjugated electron systems containing natural products such as terpenes and polyunsaturated fatty acids. Understanding the mechanism of ruthenium  1 - 3 -vinylcarbene interconversion may open the way to the development of new generation ruthenium-based latent metathesis catalyst systems. This review summarizes the most relevant pioneer work focused on metathesis of conjugated polyenes in order to open new ideas for the development of forthcoming latent metathesis catalysts and to explore different application areas.

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“…The ROMP of conjugated double bonds that contain cyclopolyenes is a remarkable method for the synthesis of conductive polymers for optoelectronics (Scheme ) …”

Section: Representative Examples Of the Conversion And Synthesis Of Cmentioning

confidence: 99%

Ruthenium‐Catalyzed Metathesis of Conjugated Polyenes

et al. 2016

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“…DArP offers the advantages of fewer synthetic steps, easier purification of the monomers compared to Stille, more environmentally benign synthesis (avoidance of stoichiometric organotin bromide byproducts), tin‐free end groups, and potentially the same or broader substrate scope—all incredibly appealing for large scale synthesis. However, concerns about insoluble material (which industrially is difficult to remove by leaching), defects, low yields, and poor performance are all significant obstacles for DArP to overcome in order to truly replace Stille.…”

Section: Introductionmentioning

confidence: 99%

Analysis of diverse direct arylation polymerization (DArP) conditions toward the efficient synthesis of polymers converging with stille polymers in organic solar cells

Livi

Gobalasingham

Thompson

et al. 2016

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

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Despite the emergence of direct arylation polymerization (DArP) as an alternative method to traditional cross‐coupling routes like Stille polymerization, the exploration of DArP polymers in practical applications like polymer solar cells (PSCs) is limited. DArP polymers tend to have a reputation for being marginally inferior to Stille counterparts due to the increased presence of defects that result from unwanted side reactions in direct arylation, such as unselective C‐H bond activation and homocoupling. We report ten DArP protocols across the three major classes of DArP to generate poly[(2,5‐bis(2‐hexyldecyloxy)phenylene)‐alt‐(4,7‐di(thiophen‐2‐yl)benzo[c][1,2,5]thiadiazole)] (PPDTBT). Through evaluation of the method and resulting photophysical and electronic properties, we show not all DArP methods are suitable for generating device‐quality alternating copolymers. When DArP PPDTBT was synthesized in superheated THF with Cs2CO3, neodecanoic acid, and P(o‐anisyl)3, it generated polymers of exceptional quality that performed comparably to Stille counterparts in both roll coated ITO‐free and spin‐coated ITO devices. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 2907–2918

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“…Pursuing new kinds of sustainable and clean energy sources, such as wind and solar power, has aroused broad interest in both academia and industry over the past decades. 2,16−21 Although several reviews are already available for organic solar cells, [3][4][5]7 lithium-ion batteries, 9,11,12 white light-emitting diodes or metal-containing polymers, 16−21 there is still a lack of papers that can provide a systematic and comprehensive survey on the fundamentals and developments of metallopolymers for energy production, storage and conservation ( Figure 1). 1 In particular, the clean and perpetually available solar power is undoubtedly one promising source for energy supplement.…”

Section: Introductionmentioning

confidence: 99%

Metallopolymers for energy production, storage and conservation

Xiang

Wong

2015

Polym. Chem.

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With the world awareness of energy crisis and low carbon economy, there is an ever-growing demand for renewable energy resources, energy saving products and reliable energy storage devices. Metallopolymers play an increasingly important role as functional materials for energy production, conservation and storage. In this review, we explore the recent advances of metallopolymers in the areas of organic solar cells, white light organic light-emitting diodes and lithium-ion batteries. The structure-property relationship of these polymers and their device performance are specially emphasized and described.Energy storage techniques, especially the lithium-ion batteries (LIBs), are of great importance in the mobile society today due to their high energy density and high output voltage. Although the LIBs that are commonly used nowadays are dominated by inorganic metal complexes in the electronic device market, the rapid progress in portable electronics, such as the ultra-thin, ultra-lightweight and flexible devices, brings new challenges to the bulky and rigid conventional LIBs. 8 For the sake of matching practical requirements and market demands, organic batteries based on redox-active polymers with robust structures have currently become an area of considerable research interest. 9−12On the other hand, lighting consumes over 20% of the total electricity produced in the earth. A majority of such energy consumption and cost comes from the traditional light sources such as incandescent bulbs and fluorescent lamps used in residential, commercial and industrial buildings. Therefore, interest and demand for more energy-efficient products for general lighting purposes is growing rapidly.Organic light-emitting diodes (OLEDs) hold promise for use in display applications and for general illumination for many reasons, including their improved efficiency and low cost. 13 Phosphorescence emissions from metal-containing materials are found to be useful for OLED applications. The efficiency of energy conversion in OLEDs can be enhanced by up to four times, which enable white OLEDs to become a potential new source of "green" solid-state lighting. By embedding metal elements into polymeric scaffolds, both of the physical and chemical characteristics of the resulting organometallic materials can be finely tuned, which combine the optical and 7 Conjugated polymers have received increasing attention as ready-processed organic semiconductor materials. Unlike pure organic conjugated polymers, mixing of metal and ligand orbitals can occur in metallopolymers, which results in special features in these materials. Especially in the Pt(II) acetylenic polymeric framework MP1, π-conjugation of the ligand is preserved through metal 22 and their photophysical properties and photovoltaic responses can be fine-tuned by structural modification of the aromatic spacer (Ar). Due to the presence of Pt(II) heavy metal which induces strong spin-orbit coupling, and thus makes singlet to triplet intersystem crossing to be rapid and efficient, Pt(II) conjugate...

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Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

Cited by 68 publications

References 217 publications

Ruthenium‐Catalyzed Metathesis of Conjugated Polyenes

Ruthenium‐Catalyzed Metathesis of Conjugated Polyenes

Analysis of diverse direct arylation polymerization (DArP) conditions toward the efficient synthesis of polymers converging with stille polymers in organic solar cells

Metallopolymers for energy production, storage and conservation

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