Polymer-supported syntheses of thiophene-containing compounds using a new type of traceless linker

Ben-Haida, Abderrazak; Hodge, Philip

doi:10.1039/c2ob06714e

Cited by 4 publications

(4 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ben-Haida et al developed a unique approach, consisting of the cleavage of polymer-supported aryl 2-thienyl ketones using a mixture of potassium tert-butoxide and water. The cleavage reaction affords the terthiophene as product [ 52 ]. Leriche et al reported in their study the formation of terthiophenes as side product: their work pursued the synthesis of star-shaped phosphorous oligothiophene derivatives, however, during the coupling reaction, with a stoichiometric amount of 2-tributylstannylthiophene and in the presence of Pd(PPh3)4 as catalyst undesired terthiophene was obtained in 20% yield [ 53 ].…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

View full text Add to dashboard Cite

Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

show abstract

Section: Synthetic Methodologiesmentioning

confidence: 99%

Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Ben-Haida and Hodge reported the synthesis of eight thiophene-containing compounds with conjugated π-electron systems using a new traceless ketone linker. 47 The linker was prepared from chloromethyl Merrifield resin 1 and 4-hydroxyphenyl 2-thienyl ketone 58 (Scheme 9). To diversify the thiophene ring, the bromo derivative 59 was subjected to Suzuki coupling with arylboronic acids 63a−63d.…”

Section: Ketone Linkersmentioning

confidence: 99%

“…The recent interest in oligomers with conjugated π-electron systems due to their potential applications in molecular electronics has driven the development of efficient synthetic routes for their preparation. Ben-Haida and Hodge reported the synthesis of eight thiophene-containing compounds with conjugated π-electron systems using a new traceless ketone linker . The linker was prepared from chloromethyl Merrifield resin 1 and 4-hydroxyphenyl 2-thienyl ketone 58 (Scheme ).…”

Section: C–h Linkersmentioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

View full text Add to dashboard Cite

Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

show abstract

“…It provided a procedure whereby reagents and byproducts were simply removed by filtration, and recrystallization of any intermediates was eliminated. Other types of π-conjugated oligomers have been reported and synthesized by a solid-phase approach, including oligo-(dialkylfluorene)s, oligo-(triarylamine)s, and alternating cooligomers thereof . Also notable is that Burke et al developed a new type of catch-and-release purification protocol for N -methyliminodiacetic acid (MIDA)-boronate-containing intermediates. , MIDA boronates absorbed on silica gel were purified by switching the eluent, thanks to their binary elution properties.…”

Section: Introductionmentioning

confidence: 99%

Integrated System Built for Small-Molecule Semiconductors via High-Throughput Approaches

Zhang

et al. 2023

J. Am. Chem. Soc.

View full text Add to dashboard Cite

High-throughput synthesis of solution-processable structurally variable small-molecule semiconductors is both an opportunity and a challenge. A large number of diverse molecules provide a possibility for quick material discovery and machine learning based on experimental data. However, the diversity of the molecular structure leads to the complexity of molecular properties, such as solubility, polarity, and crystallinity, which poses great challenges to solution processing and purification. Here, we first report an integrated system for the high-throughput synthesis, purification, and characterization of molecules with a large variety. Based on the principle "Like dissolves like," we combine theoretical calculations and a robotic platform to accelerate the purification of those molecules. With this platform, a material library containing 125 molecules and their optical-electronic properties was built within a timeframe of weeks. More importantly, the high repeatability of recrystallization we design is a reliable approach to further upgrading and industrial production.

show abstract

Polymer-supported syntheses of thiophene-containing compounds using a new type of traceless linker

Cited by 4 publications

References 52 publications

Thiophene-Based Trimers and Their Bioapplications: An Overview

Thiophene-Based Trimers and Their Bioapplications: An Overview

Traceless Solid-Phase Organic Synthesis

Integrated System Built for Small-Molecule Semiconductors via High-Throughput Approaches

Contact Info

Product

Resources

About