Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties

Controlling the supramolecular synthon outcome in systems with different functionalities has been a key factor for the design of supramolecular materials, which also affected theirphysicochemical properties. In this contribution, we have analyzed the structural landscape of α-acetamidocinnamic acid...

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Authors: Ejarque, Daniel, Calvet Pallàs, Maria Teresa, Font Bardia, Ma. Mercedes, Pons, Josefina
Format: article
Status:Versión aceptada para publicación
Publication Date:2024
Country:España
Institution:Universidad de Barcelona
Repository:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/216762
Online Access:https://hdl.handle.net/2445/216762
Access Level:Open access
Keyword:Estructura cristal·lina (Sòlids)
Cristal·lografia
Difracció
Layer structure (Solids)
Crystallography
Diffraction
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spelling Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical PropertiesEjarque, DanielCalvet Pallàs, Maria TeresaFont Bardia, Ma. MercedesPons, JosefinaEstructura cristal·lina (Sòlids)Cristal·lografiaDifraccióLayer structure (Solids)CrystallographyDiffractionControlling the supramolecular synthon outcome in systems with different functionalities has been a key factor for the design of supramolecular materials, which also affected theirphysicochemical properties. In this contribution, we have analyzed the structural landscape of α-acetamidocinnamic acid (HACA) aiming to find its synthon outcome from the competitivity between its acidic and amidic groups. We prepared four multicomponent forms including one dihydrate (HACA·2H2O) and three cocrystals bearing different bipyridine coformers with formulas(HACA)2(1,2-bpe) (1), (HACA)2(4,4′-azpy) (2), and (HACA)2(4,4′-bipy)3 (3) (1,2-bpe = 1,2-bis(4-pyridyl)ethylene; 4,4′-azpy = 4,4′-azopyridine; 4,4′-bipy = 4,4′-bipyridine). First, we applied a virtual screening approach to assess the feasibility of cocrystal formation. Then, we synthesized the cocrystals, via liquid-assisted grinding (LAG) (1 and 2) or solvothermal (3) techniques, and single crystals of HACA, and their four multicomponent forms were obtained showing different synthons and crystal packings. Besides, a Cambridge Structural Database (CSD) search of the cocrystals presenting bipyridine-type coformers and molecules with acid and amide functionalities was performed, and the observed synthon occurrences as well as the possibility of synthon modification by tuning the H-donor/H-acceptor propensity of the acidic and amidic groups were shown. Finally, we measured their thermal and photophysical properties, which were correlated with their structural features.American Chemical Society2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/216762Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.1021/acs.cgd.3c01374Crystal Growth & Design, 2024, vol. 24, num.4, p. 1746-1765https://doi.org/10.1021/acs.cgd.3c01374cc-by (c) The Authors, 2024http://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/2167622026-05-27T06:46:51Z
dc.title.none.fl_str_mv Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
title Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
spellingShingle Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
Ejarque, Daniel
Estructura cristal·lina (Sòlids)
Cristal·lografia
Difracció
Layer structure (Solids)
Crystallography
Diffraction
title_short Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
title_full Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
title_fullStr Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
title_full_unstemmed Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
title_sort Structural Landscape of α‑Acetamidocinnamic Acid Cocrystals withBipyridine-Based Coformers: Influence of Crystal Packing on TheirThermal and Photophysical Properties
dc.creator.none.fl_str_mv Ejarque, Daniel
Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
Pons, Josefina
author Ejarque, Daniel
author_facet Ejarque, Daniel
Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
Pons, Josefina
author_role author
author2 Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
Pons, Josefina
author2_role author
author
author
dc.subject.none.fl_str_mv Estructura cristal·lina (Sòlids)
Cristal·lografia
Difracció
Layer structure (Solids)
Crystallography
Diffraction
topic Estructura cristal·lina (Sòlids)
Cristal·lografia
Difracció
Layer structure (Solids)
Crystallography
Diffraction
description Controlling the supramolecular synthon outcome in systems with different functionalities has been a key factor for the design of supramolecular materials, which also affected theirphysicochemical properties. In this contribution, we have analyzed the structural landscape of α-acetamidocinnamic acid (HACA) aiming to find its synthon outcome from the competitivity between its acidic and amidic groups. We prepared four multicomponent forms including one dihydrate (HACA·2H2O) and three cocrystals bearing different bipyridine coformers with formulas(HACA)2(1,2-bpe) (1), (HACA)2(4,4′-azpy) (2), and (HACA)2(4,4′-bipy)3 (3) (1,2-bpe = 1,2-bis(4-pyridyl)ethylene; 4,4′-azpy = 4,4′-azopyridine; 4,4′-bipy = 4,4′-bipyridine). First, we applied a virtual screening approach to assess the feasibility of cocrystal formation. Then, we synthesized the cocrystals, via liquid-assisted grinding (LAG) (1 and 2) or solvothermal (3) techniques, and single crystals of HACA, and their four multicomponent forms were obtained showing different synthons and crystal packings. Besides, a Cambridge Structural Database (CSD) search of the cocrystals presenting bipyridine-type coformers and molecules with acid and amide functionalities was performed, and the observed synthon occurrences as well as the possibility of synthon modification by tuning the H-donor/H-acceptor propensity of the acidic and amidic groups were shown. Finally, we measured their thermal and photophysical properties, which were correlated with their structural features.
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/216762
url https://hdl.handle.net/2445/216762
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.1021/acs.cgd.3c01374
Crystal Growth & Design, 2024, vol. 24, num.4, p. 1746-1765
https://doi.org/10.1021/acs.cgd.3c01374
dc.rights.none.fl_str_mv cc-by (c) The Authors, 2024
http://creativecommons.org/licenses/by/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) The Authors, 2024
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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