Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene

Four new halogen-bonded cocrystals of biological methylxanthines, named caffeine, theophylline and theobromine, have been prepared with 1,4-diiodotetrafluorobenzene as a halogen bond donor by mechanochemical and solution processes. For theophylline, N⋯I and N⋯O interactions were observed, while for...

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Autores: Benito, Mónica|||0000-0001-5550-4757, Núñez, Rosario|||0000-0003-4582-5148, Sinha, Sohini|||0000-0003-0875-5080, Roscini, Claudio|||0000-0002-0157-8934, Hidalgo-Rosa, Yoan, Schott, Eduardo, Zarate, Ximena, Molins Grau, Elies|||0000-0003-1012-0551
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:302498
Acceso en línea:https://ddd.uab.cat/record/302498
https://dx.doi.org/urn:doi:10.1039/d4ce00138a
Access Level:acceso abierto
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spelling Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzenegreen synthesis, structure, photophysics and DFT studiesBenito, Mónica|||0000-0001-5550-4757Núñez, Rosario|||0000-0003-4582-5148Sinha, Sohini|||0000-0003-0875-5080Roscini, Claudio|||0000-0002-0157-8934Hidalgo-Rosa, YoanSchott, EduardoZarate, XimenaMolins Grau, Elies|||0000-0003-1012-0551Four new halogen-bonded cocrystals of biological methylxanthines, named caffeine, theophylline and theobromine, have been prepared with 1,4-diiodotetrafluorobenzene as a halogen bond donor by mechanochemical and solution processes. For theophylline, N⋯I and N⋯O interactions were observed, while for caffeine and theobromine, only N⋯I was detected. The solids were characterized by PXRD, SC-XRD, FTIR and thermal methods (TGA-DSC analyses). In addition, the solid-state photoluminescence properties of the methylxanthines and their respective cocrystals have been studied and quantum chemistry calculations have been performed to rationalise and understand the electronic and optical properties of all compounds. This work provides a triad of natural methylxanthines capable of forming halogen-bonded multicomponent systems that can give rise to a cocrystal-to-crystal transformation with off-on luminescence activation. 22024-01-0120242024-01-01Articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/302498https://dx.doi.org/urn:doi:10.1039/d4ce00138areponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengAgencia Estatal de Investigación https://doi.org/10.13039/501100011033 PID2021-1245720B-C32Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PID2022-136892NB-I00Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PID2019-106832RB-I00Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CEX2019-00917-SAgencia Estatal de Investigación https://doi.org/10.13039/501100011033 CEX2023-001263-SAgencia Estatal de Investigación https://doi.org/10.13039/501100011033 CEX2021-001214-SAgència de Gestió d'Ajuts Universitaris i de Recerca https://doi.org/10.13039/501100003030 2021/SGR-00442Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 TED2021-131709B-I00European Commission https://doi.org/10.13039/501100000780 754397open accesshttp://purl.org/coar/access_right/c_abf2Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original.https://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:3024982026-06-06T12:50:31Z
dc.title.none.fl_str_mv Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
green synthesis, structure, photophysics and DFT studies
title Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
spellingShingle Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
Benito, Mónica|||0000-0001-5550-4757
title_short Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
title_full Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
title_fullStr Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
title_full_unstemmed Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
title_sort Methylxanthines for halogen bonded cocrystals with 1,4-diiodotetrafluorobenzene
dc.creator.none.fl_str_mv Benito, Mónica|||0000-0001-5550-4757
Núñez, Rosario|||0000-0003-4582-5148
Sinha, Sohini|||0000-0003-0875-5080
Roscini, Claudio|||0000-0002-0157-8934
Hidalgo-Rosa, Yoan
Schott, Eduardo
Zarate, Ximena
Molins Grau, Elies|||0000-0003-1012-0551
author Benito, Mónica|||0000-0001-5550-4757
author_facet Benito, Mónica|||0000-0001-5550-4757
Núñez, Rosario|||0000-0003-4582-5148
Sinha, Sohini|||0000-0003-0875-5080
Roscini, Claudio|||0000-0002-0157-8934
Hidalgo-Rosa, Yoan
Schott, Eduardo
Zarate, Ximena
Molins Grau, Elies|||0000-0003-1012-0551
author_role author
author2 Núñez, Rosario|||0000-0003-4582-5148
Sinha, Sohini|||0000-0003-0875-5080
Roscini, Claudio|||0000-0002-0157-8934
Hidalgo-Rosa, Yoan
Schott, Eduardo
Zarate, Ximena
Molins Grau, Elies|||0000-0003-1012-0551
author2_role author
author
author
author
author
author
author
description Four new halogen-bonded cocrystals of biological methylxanthines, named caffeine, theophylline and theobromine, have been prepared with 1,4-diiodotetrafluorobenzene as a halogen bond donor by mechanochemical and solution processes. For theophylline, N⋯I and N⋯O interactions were observed, while for caffeine and theobromine, only N⋯I was detected. The solids were characterized by PXRD, SC-XRD, FTIR and thermal methods (TGA-DSC analyses). In addition, the solid-state photoluminescence properties of the methylxanthines and their respective cocrystals have been studied and quantum chemistry calculations have been performed to rationalise and understand the electronic and optical properties of all compounds. This work provides a triad of natural methylxanthines capable of forming halogen-bonded multicomponent systems that can give rise to a cocrystal-to-crystal transformation with off-on luminescence activation.
publishDate 2024
dc.date.none.fl_str_mv 2
2024-01-01
2024
2024-01-01
dc.type.none.fl_str_mv 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://ddd.uab.cat/record/302498
https://dx.doi.org/urn:doi:10.1039/d4ce00138a
url https://ddd.uab.cat/record/302498
https://dx.doi.org/urn:doi:10.1039/d4ce00138a
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PID2021-1245720B-C32
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PID2022-136892NB-I00
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PID2019-106832RB-I00
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CEX2019-00917-S
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CEX2023-001263-S
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CEX2021-001214-S
Agència de Gestió d'Ajuts Universitaris i de Recerca https://doi.org/10.13039/501100003030 2021/SGR-00442
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 TED2021-131709B-I00
European Commission https://doi.org/10.13039/501100000780 754397
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by-nc/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
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instname:Universitat Autònoma de Barcelona
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