High-efficiency non-thermal plasma synthesis of imine macrocycles

Patrycja Roszkowska; Abbie M. Scholes; James L. Walsh; Timothy L. Easun; Anna G. Slater

doi:10.1039/d4re00061g

High-efficiency non-thermal plasma synthesis of imine macrocycles

Patrycja Roszkowska, Abbie M. Scholes, James L. Walsh^*, Timothy L. Easun^*, Anna G. Slater^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

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Abstract

Macrocycles are candidates for wide-ranging applications, yet their synthesis can be low-yielding, poorly reproducible, and resource-intensive, limiting their use. Here, we explore the use of Non-Thermal Plasma (NTP) as an efficient method for the synthesis of imine macrocycles at the gram scale. NTP-mediated macrocyclisations consistently achieved high yields of up to 97% in reduced reaction times compared to the standard non-plasma method, and were successfully carried out with a range of different aldehyde substrates. Control experiments were performed to explore the origin of the observed improvements. The results indicate that NTP methods could be advantageous for macrocycle synthesis, particularly for substrates that are sensitive to elevated temperature, and other materials formed via imine condensation.

Original language	English
Number of pages	8
Journal	Reaction Chemistry and Engineering
Early online date	8 Apr 2024
DOIs	https://doi.org/10.1039/d4re00061g
Publication status	E-pub ahead of print - 8 Apr 2024

Bibliographical note

Acknowledgements
TLE thanks the University of Birmingham, and gratefully acknowledges the Royal Society for the award of a University Research Fellowship (6866 and URF\R\201028). JW would like to acknowledge EPSRC grant EP/S025790/1. AGS thanks the Royal Society and the Engineering and Physical Sciences Research Council (EPSRC) for a Royal Society-EPSRC Dorothy Hodgkin Fellowship (DH150156), the Royal Society for a University Research Fellowship (URF\R1\201168) and a Research Grant (RSG\R1\180357), AGS and AS thank the Royal Society for an Enhancement Award (RGF\EA\180194) that supported this work and a PhD studentship, and AGS and PR thank the University of Liverpool for a PhD studentship via the Doctoral Training Partnership allocation. This work made use of equipment from the Analytical Services/Department of Chemistry at the University of Liverpool as well as shared equipment at the Materials Innovation Factory (MIF) created as part of the UK Research Partnership Innovation Fund (Research England) and co-funded by the Sir Henry Royce Institute.

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Photogated nanofluidics: from single crystal diffusion control to water purification
Easun, T.
The Royal Society
1/10/22 → 31/03/25
Project: Research Councils

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title = "High-efficiency non-thermal plasma synthesis of imine macrocycles",

abstract = "Macrocycles are candidates for wide-ranging applications, yet their synthesis can be low-yielding, poorly reproducible, and resource-intensive, limiting their use. Here, we explore the use of Non-Thermal Plasma (NTP) as an efficient method for the synthesis of imine macrocycles at the gram scale. NTP-mediated macrocyclisations consistently achieved high yields of up to 97% in reduced reaction times compared to the standard non-plasma method, and were successfully carried out with a range of different aldehyde substrates. Control experiments were performed to explore the origin of the observed improvements. The results indicate that NTP methods could be advantageous for macrocycle synthesis, particularly for substrates that are sensitive to elevated temperature, and other materials formed via imine condensation.",

author = "Patrycja Roszkowska and Scholes, {Abbie M.} and Walsh, {James L.} and Easun, {Timothy L.} and Slater, {Anna G.}",

note = "Acknowledgements TLE thanks the University of Birmingham, and gratefully acknowledges the Royal Society for the award of a University Research Fellowship (6866 and URF\R\201028). JW would like to acknowledge EPSRC grant EP/S025790/1. AGS thanks the Royal Society and the Engineering and Physical Sciences Research Council (EPSRC) for a Royal Society-EPSRC Dorothy Hodgkin Fellowship (DH150156), the Royal Society for a University Research Fellowship (URF\R1\201168) and a Research Grant (RSG\R1\180357), AGS and AS thank the Royal Society for an Enhancement Award (RGF\EA\180194) that supported this work and a PhD studentship, and AGS and PR thank the University of Liverpool for a PhD studentship via the Doctoral Training Partnership allocation. This work made use of equipment from the Analytical Services/Department of Chemistry at the University of Liverpool as well as shared equipment at the Materials Innovation Factory (MIF) created as part of the UK Research Partnership Innovation Fund (Research England) and co-funded by the Sir Henry Royce Institute.",

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AU - Roszkowska, Patrycja

AU - Scholes, Abbie M.

AU - Walsh, James L.

AU - Easun, Timothy L.

AU - Slater, Anna G.

N1 - Acknowledgements TLE thanks the University of Birmingham, and gratefully acknowledges the Royal Society for the award of a University Research Fellowship (6866 and URF\R\201028). JW would like to acknowledge EPSRC grant EP/S025790/1. AGS thanks the Royal Society and the Engineering and Physical Sciences Research Council (EPSRC) for a Royal Society-EPSRC Dorothy Hodgkin Fellowship (DH150156), the Royal Society for a University Research Fellowship (URF\R1\201168) and a Research Grant (RSG\R1\180357), AGS and AS thank the Royal Society for an Enhancement Award (RGF\EA\180194) that supported this work and a PhD studentship, and AGS and PR thank the University of Liverpool for a PhD studentship via the Doctoral Training Partnership allocation. This work made use of equipment from the Analytical Services/Department of Chemistry at the University of Liverpool as well as shared equipment at the Materials Innovation Factory (MIF) created as part of the UK Research Partnership Innovation Fund (Research England) and co-funded by the Sir Henry Royce Institute.

PY - 2024/4/8

Y1 - 2024/4/8

N2 - Macrocycles are candidates for wide-ranging applications, yet their synthesis can be low-yielding, poorly reproducible, and resource-intensive, limiting their use. Here, we explore the use of Non-Thermal Plasma (NTP) as an efficient method for the synthesis of imine macrocycles at the gram scale. NTP-mediated macrocyclisations consistently achieved high yields of up to 97% in reduced reaction times compared to the standard non-plasma method, and were successfully carried out with a range of different aldehyde substrates. Control experiments were performed to explore the origin of the observed improvements. The results indicate that NTP methods could be advantageous for macrocycle synthesis, particularly for substrates that are sensitive to elevated temperature, and other materials formed via imine condensation.

AB - Macrocycles are candidates for wide-ranging applications, yet their synthesis can be low-yielding, poorly reproducible, and resource-intensive, limiting their use. Here, we explore the use of Non-Thermal Plasma (NTP) as an efficient method for the synthesis of imine macrocycles at the gram scale. NTP-mediated macrocyclisations consistently achieved high yields of up to 97% in reduced reaction times compared to the standard non-plasma method, and were successfully carried out with a range of different aldehyde substrates. Control experiments were performed to explore the origin of the observed improvements. The results indicate that NTP methods could be advantageous for macrocycle synthesis, particularly for substrates that are sensitive to elevated temperature, and other materials formed via imine condensation.

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DO - 10.1039/d4re00061g

M3 - Article

SN - 2058-9883

JO - Reaction Chemistry and Engineering

JF - Reaction Chemistry and Engineering

ER -

High-efficiency non-thermal plasma synthesis of imine macrocycles

Abstract

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Photogated nanofluidics: from single crystal diffusion control to water purification

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