A Direct C–H Coupling Method for Preparing π-Conjugated Functional Polymers with High Regioregularity

Zhang, Qiang; Chang, Meijia; Lu, Yan; Sun, Yanna; Li, Chenxi; Yang, Xinlin; Zhang, Mingtao; Chen, Yongsheng

doi:10.1021/acs.macromol.7b02390

Cited by 43 publications

(37 citation statements)

References 60 publications

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“…However, when an ester function was incorporated into the side‐chain, the yield and regioregularity were improved considerably ( Figure ) . The nature of the side‐chain directing group is also shown to have a considerable influence on structural regularity, with regioregularity up to 99% observed with sulfinyl and sulfonyl groups in ligand‐free conditions ( Figure ) . The proposed mechanistic reason for the high regioregularity observed in the presence of certain bulky directing groups is that it is sterically unfavorable for two of these directing groups to coordinate the Pd catalyst simultaneously.…”

Section: Recent Developments and Future Directionsmentioning

confidence: 99%

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CH Activation as a Shortcut to Conjugated Polymer Synthesis

Blaskovits

Leclerc

2018

Macromol. Rapid Commun.

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Direct (hetero)arylation polymerization exploits the palladium-catalyzed activation of aromatic CH bonds for the atom-economical synthesis of conjugated polymers for a wide range of applications. This account outlines how direct arylation methodologies overcome many of the limitations of contemporary polymerization techniques at both the research and production scale, and explains how monomer design and reaction conditions must be tailored to ensure high polymer molecular weight, yield, and structural integrity. Current research aims to improve further this reaction's profile as a sustainable methodology while at the same time making it competitive with the Migita-Stille and Miyaura-Suzuki polymerizations both in scope of accessible structures and synthetic efficiency. This feature article charts the recent developments and future directions of CH activation research as it moves toward becoming at once an industrially feasible, environmentally friendly, and synthetically powerful polymerization technique.

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Section: Recent Developments and Future Directionsmentioning

confidence: 99%

“…The influence of the directing group on oxidative direct arylation polymerization, along with possible coupling motifs …”

Section: Recent Developments and Future Directionsmentioning

confidence: 99%

CH Activation as a Shortcut to Conjugated Polymer Synthesis

Blaskovits

Leclerc

2018

Macromol. Rapid Commun.

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“…And the understanding was limited to macroscopic properties, so effects of branches from low BC to high BC on molecular level were studied by MD simulation. Branch was considered as a nucleation seed in nucleation and a defect in crystal growth process in extended chain crystallization . BC was a key factor to influence crystallinity and increasing of BC decreased chain folding and changed chain conformation .…”

Section: Introductionmentioning

confidence: 99%

“…Critical BC 50/1000 C (50 branches per 1000 backbone CH 2 ) was a transition point for conformations changing from ordered to coil‐like structures when Sharkh and Hussein and Choi et al conducted simulations of BC from 10/1000 C to 80/1000 C. The transition from lamellae crystal to bundle crystal and further investigation will be considered in our simulation. Branch co‐crystallization was found to become difficult for less flexible branch, and branch with length above 10 included in crystal unit . However, only one branch along 200 backbone CH 2 was studied in BL effect study, and up to now backbone chain in simulations for BC effects were no longer than 2000 CH 2 .…”

Section: Introductionmentioning

confidence: 99%

Effects of Branch Content and Branch Length on Polyethylene Crystallization: Molecular Dynamics Simulation

Gao

Shao

et al. 2016

Macro Theory & Simulations

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Influences of branch content (BC) and branch length (BL) on isothermal crystallization of precisely branched polyethylene are studied by molecular dynamics simulation. Branch acts as a defect both in nucleation and crystal growth process. BC affects not only crystallization kinetics but also final morphologies. Crystallization rate and crystallinity decrease as BC increases. Morphology Regimes change from lamellae crystal to bundle crystal at critical BC (20/1000 C) because of different folding pattern. 50 CH2 is the critical methyl sequence length to form lamellae crystal. Lamellae thicknesses of final morphologies decrease in gradient corresponding to Morphologies Regimes. BL has no influence on the crystallization kinetics, and only affects the final morphologies when more branches inclusion happens with BL increasing. Trans‐rich phenomenon in pre‐crystalline state is observed. Crystallization process begins at the end of induction stage when trans state population reaches a critical value, and this value is independent of BC and BL.

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“…In 2018, Lu and Chen et al . developed a system to synthesize alternating copolymers with 3,3′‐bis‐(octylsulfonyl)‐2,2′‐bithiophene as one of the substrates . Kanbara et al .…”

Section: Developments Of Polymerization Methods For Large Scale Produmentioning

confidence: 99%

Towards Green Synthesis and Processing of Organic Solar Cells

Huang

Luscombe

2019

The Chemical Record

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In 2018, several major breakthroughs have been achieved in organic solar cells (OSCs) with the record power conversion efficiency (PCE) reaching over 17 %. With this increased efficiency, it is time to take a step forward to consider how to convert this technology into large scale production. For this, the economic and environmental profile of OSCs should be taken seriously‐simplified synthetic routes and green chemistry methods should be applied. According to previous studies, OSCs are competitive and profitable in the commercial market. However, toxic and/or hazardous chemicals are currently used in materials synthesis and device fabrication of OSCs. In this account, we will talk about contributions and efforts we have made to minimize the economic and environmental disadvantages in the production of OSCs. We will start with the background on how our projects were conceived and will specifically discuss our work on direct arylation and green solvent. Developments of direct arylation for synthesizing conjugated polymers will be illustrated along with our recent finding regarding the effect of green solvents on device performance and stability.

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A Direct C–H Coupling Method for Preparing π-Conjugated Functional Polymers with High Regioregularity

Cited by 43 publications

References 60 publications

CH Activation as a Shortcut to Conjugated Polymer Synthesis

CH Activation as a Shortcut to Conjugated Polymer Synthesis

Effects of Branch Content and Branch Length on Polyethylene Crystallization: Molecular Dynamics Simulation

Towards Green Synthesis and Processing of Organic Solar Cells

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