Facile green synthesis of isoindigo-based conjugated polymers using aldol polycondensation

Zhang, Guobing; Dai, Yanrong; Liu, Yu; Liu, Jiaqing; Lu, Hongbo; Qiu, Longzhen; Cho, Kilwon

doi:10.1039/c7py00484b

Cited by 44 publications

(43 citation statements)

References 31 publications

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“…Acid‐catalyzed aldol polymerization was used to link the two monomers, and two polymers, LPPV‐1 and LPPV‐2 , with different alkyl chain lengths were synthesized. The aldol polymerization was optimized by tuning the reaction conditions, including the solvent, catalyst, dehydrant, and reaction time (see Table S1 in the Supporting Information) . We found that the products were almost insoluble in common organic solvents if solid dehydrants were added.…”

Section: Figurementioning

confidence: 99%

Rigid Coplanar Polymers for Stable n‐Type Polymer Thermoelectrics

et al. 2019

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Section: Figurementioning

confidence: 99%

Rigid Coplanar Polymers for Stable n‐Type Polymer Thermoelectrics

et al. 2019

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“…Previously reported aldol condensation usually adopted p ‐toluene sulfonic acid as catalyst and the polymerization required several hours or even longer time under high temperature (≈140 °C). [ 44,47,48 ] In contrast, the modified aldol condensation in our article requires shorter time (less than 1 h) and much lower temperature (about 70 °C). Moreover, the aldol condensation using TEA as catalysts showed low sensitivity to the reaction solvents.…”

Section: Resultsmentioning

confidence: 88%

Aldol Condensation‐Polymerized n‐Doped Conjugated Polyelectrolytes for High‐Performance Nonfullerene Polymer Solar Cells

et al. 2020

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Doping provides an efficient strategy to control the electronic properties of organic semiconductors. However, compared with the widely reported p-type doping protocols, n-type doping of organic semiconductors still remains a challenge. Herein, a series of novel n-doped conjugated polyelectrolytes (CPEs) with high doping levels and conductivity are designed. These CPEs are synthesized via a facile, metal-free, and high-yield aldol condensation protocol from bis-isatin and bis-oxindole monomers. The designed CPEs possess a n-type electron-deficient and rigid conjugated backbone, resulting in easy charge delocalization, enhanced n-doping behaviors, and high conductivity. The evolution on the counterions of these CPEs further alters their n-doping behaviors, charge transporting properties, and work function tunability, etc. By using these CPEs as electron transport materials (ETMs) for nonfullerene polymer solar cells (NF-PSCs), high power conversion efficiencies (PCEs) over 16% can be achieved when PM6:Y6 is used as the active component. Moreover, these CPEs can enable efficient NF-PSCs even if their thicknesses are up to 60 nm, indicating the potential of these CPEs as thickness-insensitive ETMs for the fabrication of large-area NF-PSCs.

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“…[ 59,60 ] An alternative environmentally friendly and highly atom economical synthetic strategy is the use of Aldol (poly)condensations between different aromatic units. [ 61,62 ] Nonetheless, both of these synthetic strategies are currently still limited to monomers with specific molecular motifs that render them compatible with the employed reaction conditions. The final consideration for the upscaling of these materials is a shift from batch to flow processes to supply any potential future markets with sufficient quantities of material.…”

Section: Materials Considerationsmentioning

confidence: 99%

Challenges to the Success of Commercial Organic Photovoltaic Products

Moser

Wadsworth

Gasparini

et al. 2021

Advanced Energy Materials

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Recent advances in the development of organic photovoltaic (OPV) materials has led to significant improvements in device performance; now closing in on the 20% efficiency threshold. Despite these improvements in performance, the commercial viability of organic photovoltaic products remains elusive. In this perspective, the current limitations of high performing blends are uncovered, particularly focusing on the industrial upscaling considerations of these materials, such as synthetic scalability, active layer processing, and device stability. Moreover, a simplified metric, namely, the scalability factor (SF), is introduced to evaluate the scale‐up potential of specific OPV materials and blends thereof. Of the most popular molecular design strategies investigated in recent times, it is found that the use of Y‐series nonfullerene acceptors (NFAs) and synthetically simple materials, such as PTQ‐10 and ternary blends, are most effective at maximizing the efficiency without negatively impacting the SF. Furthermore, the improvements that are needed, in terms of device processability and stability, are considered for industrial scale‐up and final product application. Finally, an outlook of organic photovoltaics is provided both from a perspective of important research avenues and applications that can be exploited.

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Facile green synthesis of isoindigo-based conjugated polymers using aldol polycondensation

Abstract: A green and efficient synthetic protocol suitable for the preparation of isoindigo-based polymer was developed using aldol polymerization.

Cited by 44 publications

References 31 publications

Rigid Coplanar Polymers for Stable n‐Type Polymer Thermoelectrics

Rigid Coplanar Polymers for Stable n‐Type Polymer Thermoelectrics

Aldol Condensation‐Polymerized n‐Doped Conjugated Polyelectrolytes for High‐Performance Nonfullerene Polymer Solar Cells

Challenges to the Success of Commercial Organic Photovoltaic Products

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