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2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study

A novel thiophene derivative, namely 2,5-diisopropenylthiophene (DIT) was synthetized by Suzuki–Miyaura cross-coupling reaction (SMCCR). The influence of reaction parameters, such as temperature, solvent, stoichiometry of reagents, role of the base and reaction medium were thoroughly discussed in vi...

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Autores principales: Tavella, Christian, Luciano, Giorgio, Lova, Paola, Patrini, Maddalena, D'Arrigo, Cristina, Comoretto, Davide, Stagnaro, Paola
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8985149/
https://www.ncbi.nlm.nih.gov/pubmed/35424896
http://dx.doi.org/10.1039/d2ra00654e
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author Tavella, Christian
Luciano, Giorgio
Lova, Paola
Patrini, Maddalena
D'Arrigo, Cristina
Comoretto, Davide
Stagnaro, Paola
author_facet Tavella, Christian
Luciano, Giorgio
Lova, Paola
Patrini, Maddalena
D'Arrigo, Cristina
Comoretto, Davide
Stagnaro, Paola
author_sort Tavella, Christian
collection PubMed
description A novel thiophene derivative, namely 2,5-diisopropenylthiophene (DIT) was synthetized by Suzuki–Miyaura cross-coupling reaction (SMCCR). The influence of reaction parameters, such as temperature, solvent, stoichiometry of reagents, role of the base and reaction medium were thoroughly discussed in view of yield optimization and environmental impact minimization. Basic design of experiment (DoE) and multiple linear regression (MLR) modeling methods were used to interpret the obtained results. DIT was then employed as a comonomer in the copolymerization with waste elemental sulfur through a green process, inverse vulcanization (IV), to obtain sulfur-rich polymers named inverse vulcanized polymers (IVPs) possessing high refractive index (n ≈ 1.8). The DIT comonomer was purposely designed to (i) favor the IV process owing to the high reactivity of the isopropenyl functionalities and (ii) enhance the refractive index of the ensuing IVPs owing to the presence of the sulfur atom itself and to the high electronic polarizability of the π-conjugated thiophene ring. A series of random sulfur-r-diisopropenylthiophene (S-r-DIT) copolymers with sulfur content from 50 up to 90 wt% were synthesized by varying the S/DIT feed ratio. Spectroscopic, thermal and optical characterizations of the new IVPs were carried out to assess their main chemical–physical features.
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spelling pubmed-89851492022-04-13 2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study Tavella, Christian Luciano, Giorgio Lova, Paola Patrini, Maddalena D'Arrigo, Cristina Comoretto, Davide Stagnaro, Paola RSC Adv Chemistry A novel thiophene derivative, namely 2,5-diisopropenylthiophene (DIT) was synthetized by Suzuki–Miyaura cross-coupling reaction (SMCCR). The influence of reaction parameters, such as temperature, solvent, stoichiometry of reagents, role of the base and reaction medium were thoroughly discussed in view of yield optimization and environmental impact minimization. Basic design of experiment (DoE) and multiple linear regression (MLR) modeling methods were used to interpret the obtained results. DIT was then employed as a comonomer in the copolymerization with waste elemental sulfur through a green process, inverse vulcanization (IV), to obtain sulfur-rich polymers named inverse vulcanized polymers (IVPs) possessing high refractive index (n ≈ 1.8). The DIT comonomer was purposely designed to (i) favor the IV process owing to the high reactivity of the isopropenyl functionalities and (ii) enhance the refractive index of the ensuing IVPs owing to the presence of the sulfur atom itself and to the high electronic polarizability of the π-conjugated thiophene ring. A series of random sulfur-r-diisopropenylthiophene (S-r-DIT) copolymers with sulfur content from 50 up to 90 wt% were synthesized by varying the S/DIT feed ratio. Spectroscopic, thermal and optical characterizations of the new IVPs were carried out to assess their main chemical–physical features. The Royal Society of Chemistry 2022-03-22 /pmc/articles/PMC8985149/ /pubmed/35424896 http://dx.doi.org/10.1039/d2ra00654e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Tavella, Christian
Luciano, Giorgio
Lova, Paola
Patrini, Maddalena
D'Arrigo, Cristina
Comoretto, Davide
Stagnaro, Paola
2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
title 2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
title_full 2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
title_fullStr 2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
title_full_unstemmed 2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
title_short 2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
title_sort 2,5-diisopropenylthiophene by suzuki–miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8985149/
https://www.ncbi.nlm.nih.gov/pubmed/35424896
http://dx.doi.org/10.1039/d2ra00654e
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