Simple procedure for mono- and bis-end-functionalization of regioregular poly(3-hexylthiophene)s using chalcogens

Luscombe, Christine K.

doi:10.1039/c3cc47560c

Cited by 35 publications

(37 citation statements)

References 34 publications

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“…[9] Subsequently,t he reaction mixture was divided into two portions with one quenched using sulfur powder and the other quenched with 5 m HCl. [9] Subsequently,t he reaction mixture was divided into two portions with one quenched using sulfur powder and the other quenched with 5 m HCl.…”

supporting

confidence: 81%

Chemical‐Bonding‐Directed Hierarchical Assembly of Nanoribbon‐Shaped Nanocomposites of Gold Nanorods and Poly(3‐hexylthiophene)

Pan

Peng

et al. 2016

Angew Chem Int Ed

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Nanoribbon-shaped nanocomposites composed of conjugated polymer poly(3-hexylthiophene) (P3HT) nanoribbons and plasmonic gold nanorods (AuNRs) were crafted by a co-assembly of thiol-terminated P3HT (P3HT-SH) nanofibers with dodecanethiol-coated AuNRs (AuNRs-DDT). First, P3HT-SH nanofibers were formed due to interchain π-π stacking. Upon the addition of AuNRs-DDT, P3HT-SH nanofibers were transformed into nanoribbons decorated with the aligned AuNRs on the surface (i.e., nanoribbon-like P3HT/AuNRs nanocomposites). Depending on the surface coverage of the P3HT nanoribbons by AuNRs, these hierarchically assembled nanocomposites exhibited broadened and red-shifted absorption bands of AuNRs in nIR region due to the plasmon coupling of adjacent aligned AuNRs and displayed quenched photoluminescence of P3HT. Such conjugated polymer/plasmonic nanorod nanocomposites may find applications in fields, such as building blocks for complex superstructures, optical biosensors, and optoelectronic devices.

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supporting

confidence: 81%

Chemical‐Bonding‐Directed Hierarchical Assembly of Nanoribbon‐Shaped Nanocomposites of Gold Nanorods and Poly(3‐hexylthiophene)

Pan

Peng

et al. 2016

Angew Chem Int Ed

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“…Depending on the electronics of the organometallic reagents, mono‐ or di‐capped polymers could be prepared that could be further functionalized via post‐polymerization modification . Building on the benefits of incorporating chain‐end thiols for macromolecular design described earlier, Okamoto and Luscombe reported the use of in situ quenching of the polymerization with sulfur powder or triisopropylsilanethiol to selectively install thiol end groups at the ω‐chain‐end or at both the α and ω‐chain‐ends, respectively …”

Section: Discussionmentioning

confidence: 99%

Established and emerging strategies for polymer chain‐end modification

Lunn

Discekici

Alaniz

et al. 2017

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

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The development of "controlled" and "living" polymerization processes with high end-group fidelity has enabled an unprecedented range of polymeric materials with specific chainend functionality to be prepared. This highlight provides an overview of available strategies and evaluation of recent approaches for the chain-end functionalization of polymers prepared through controlled chain-growth polymerizations. As a tribute to Professor Robert B. Grubbs on the occasion of his 75th birthday, we also take this opportunity to highlight methods for the chain-end modification of polymers prepared by ring-opening metathesis polymerization within the broader context of functional group tolerant, living polymerizations. Finally, we focus attention toward new directions in polymer chain-end modifications, describing existing gaps in current strategies, and detailing recently reported protocols that show significant improvements over traditional methods.

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“…Nucleophilic addition of Grignard reagent (8) to the pre‐functionalized Ni complex (11) gives complex (12), which starts the growth of the polymer chain giving a precisely end‐capped fully regioregular P3HT with high molecular weight and low dispersity. We later explored simple quenching techniques after the KCTP synthesis of P3HT and successfully obtained regioregular P3HT with chalcogen end groups, either on one or both ends . These end group modifications enable us to tune the compatibility between P3HT and other materials, improving the performance of organic semiconductor hybrid materials…”

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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Simple procedure for mono- and bis-end-functionalization of regioregular poly(3-hexylthiophene)s using chalcogens

Cited by 35 publications

References 34 publications

Chemical‐Bonding‐Directed Hierarchical Assembly of Nanoribbon‐Shaped Nanocomposites of Gold Nanorods and Poly(3‐hexylthiophene)

Chemical‐Bonding‐Directed Hierarchical Assembly of Nanoribbon‐Shaped Nanocomposites of Gold Nanorods and Poly(3‐hexylthiophene)

Established and emerging strategies for polymer chain‐end modification

Towards Green Synthesis and Processing of Organic Solar Cells

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