Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage

Molecular solar thermal (MOST) energy storage systems are getting increased attention related to renewable energy storage applications. Particularly, 2,3-difunctionalized norbornadiene-quadricyclane (NBD-QC) switches bearing a nitrile (CN) group as one of the two substituents are investigated as pro...

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Detalles Bibliográficos
Autores: Baggi, Nicolò|||0000-0003-4743-5151, Hölzel, Helen, Schomaker, Hannes, Moreno, Kevin, Moth-Poulsen, Kasper|||0000-0003-4018-4927
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/402355
Acceso en línea:https://hdl.handle.net/2117/402355
https://dx.doi.org/10.1002/cssc.202301184
Access Level:acceso abierto
Palabra clave:Solar thermal energy
Energy storage
Energia tèrmica solar
Energia -- Emmagatzematge
Àrees temàtiques de la UPC::Energies
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spelling Flow-integrated preparation of norbornadiene precursors for solar thermal energy storageBaggi, Nicolò|||0000-0003-4743-5151Hölzel, HelenSchomaker, HannesMoreno, KevinMoth-Poulsen, Kasper|||0000-0003-4018-4927Solar thermal energyEnergy storageEnergia tèrmica solarEnergia -- EmmagatzematgeÀrees temàtiques de la UPC::EnergiesMolecular solar thermal (MOST) energy storage systems are getting increased attention related to renewable energy storage applications. Particularly, 2,3-difunctionalized norbornadiene-quadricyclane (NBD-QC) switches bearing a nitrile (CN) group as one of the two substituents are investigated as promising MOST candidates thanks to their high energy storage densities and their red-shifted absorbance. Moreover, such NBD systems can be prepared in large quantities (a requirement for MOST-device applications) in flow through Diels-Alder reaction between cyclopentadiene and appropriately functionalized propynenitriles. However, these acetylene precursors are traditionally prepared in batch from their corresponding acetophenones using reactive chemicals potentially leading to health and physical hazards, especially when working on a several-grams scale. Here, we develop a multistep flow-chemistry route to enhance the production of these crucial precursors. Furthermore, we assess the atom economy (AE) and the E-factor showing improved green metrics compared to classical batch methods. Our results pave the way for a complete flow synthesis of NBDs with a positive impact on green chemistry aspects.The authors acknowledge funding from the European Commis- sion (H2020-FETPROACT-2019-951801; Molecular Solar-Thermal Energy Storage Systems) and the European Research Council (ERC) under grant agreement CoG, PHOTHERM – 101002131. The authors would like to also acknowledge the financial support from the Göran Gustafsson Foundation, the Swedish Research Council, and the Catalan Institute of Advanced Studies (ICREA)Peer Reviewed20232023-01-0120242024-02-21journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/402355https://dx.doi.org/10.1002/cssc.202301184reponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/4023552026-05-27T15:37:01Z
dc.title.none.fl_str_mv Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
title Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
spellingShingle Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
Baggi, Nicolò|||0000-0003-4743-5151
Solar thermal energy
Energy storage
Energia tèrmica solar
Energia -- Emmagatzematge
Àrees temàtiques de la UPC::Energies
title_short Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
title_full Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
title_fullStr Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
title_full_unstemmed Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
title_sort Flow-integrated preparation of norbornadiene precursors for solar thermal energy storage
dc.creator.none.fl_str_mv Baggi, Nicolò|||0000-0003-4743-5151
Hölzel, Helen
Schomaker, Hannes
Moreno, Kevin
Moth-Poulsen, Kasper|||0000-0003-4018-4927
author Baggi, Nicolò|||0000-0003-4743-5151
author_facet Baggi, Nicolò|||0000-0003-4743-5151
Hölzel, Helen
Schomaker, Hannes
Moreno, Kevin
Moth-Poulsen, Kasper|||0000-0003-4018-4927
author_role author
author2 Hölzel, Helen
Schomaker, Hannes
Moreno, Kevin
Moth-Poulsen, Kasper|||0000-0003-4018-4927
author2_role author
author
author
author
dc.subject.none.fl_str_mv Solar thermal energy
Energy storage
Energia tèrmica solar
Energia -- Emmagatzematge
Àrees temàtiques de la UPC::Energies
topic Solar thermal energy
Energy storage
Energia tèrmica solar
Energia -- Emmagatzematge
Àrees temàtiques de la UPC::Energies
description Molecular solar thermal (MOST) energy storage systems are getting increased attention related to renewable energy storage applications. Particularly, 2,3-difunctionalized norbornadiene-quadricyclane (NBD-QC) switches bearing a nitrile (CN) group as one of the two substituents are investigated as promising MOST candidates thanks to their high energy storage densities and their red-shifted absorbance. Moreover, such NBD systems can be prepared in large quantities (a requirement for MOST-device applications) in flow through Diels-Alder reaction between cyclopentadiene and appropriately functionalized propynenitriles. However, these acetylene precursors are traditionally prepared in batch from their corresponding acetophenones using reactive chemicals potentially leading to health and physical hazards, especially when working on a several-grams scale. Here, we develop a multistep flow-chemistry route to enhance the production of these crucial precursors. Furthermore, we assess the atom economy (AE) and the E-factor showing improved green metrics compared to classical batch methods. Our results pave the way for a complete flow synthesis of NBDs with a positive impact on green chemistry aspects.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-01-01
2024
2024-02-21
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/2117/402355
https://dx.doi.org/10.1002/cssc.202301184
url https://hdl.handle.net/2117/402355
https://dx.doi.org/10.1002/cssc.202301184
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:UPCommons. Portal del coneixement obert de la UPC
instname:Universitat Politècnica de Catalunya (UPC)
instname_str Universitat Politècnica de Catalunya (UPC)
reponame_str UPCommons. Portal del coneixement obert de la UPC
collection UPCommons. Portal del coneixement obert de la UPC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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