Structural landscape of α‑acetamidocinnamic acid cocrystals with bipyridine-based coformers : influence of crystal packing on their thermal and photophysical properties
Ejarque, Daniel (Universitat Autònoma de Barcelona. Departament de Química)
Calvet, Teresa (Universitat de Barcelona. Departament de Mineralogia, Petrologia i Geologia Aplicada)
Font-Bardia, Mercè (Universitat de Barcelona. Unitat de Difracció de Raig-X)
Pons Picart, Josefina (Universitat Autònoma de Barcelona. Departament de Química)

Data:	2024
Resum:	Controlling the supramolecular synthon outcome in systems with different functionalities has been a key factor for the design of supramolecular materials, which also affected their physicochemical 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·2H 2O) 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.
Ajuts:	"la Caixa" Foundation CB615921 "la Caixa" Foundation CB616406 Agència de Gestió d'Ajuts Universitaris i de Recerca 2021/SGR-00262
Nota:	Altres ajuts: acords transformatius de la UAB
Drets:	Aquest 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, fins i tot amb finalitats comercials, sempre i quan es reconegui l'autoria de l'obra original.
Llengua:	Anglès
Document:	Article ; recerca ; Versió publicada
Matèria:	Crystal structure ; Crystals ; Diffraction ; Energy ; Organic synthesis
Publicat a:	Crystal Growth and Design, Vol. 24, Issue 4 (February 2024) , p. 1746-1765, ISSN 1528-7505
Obra relacionada:	Ejarque, Daniel;Calvet, Teresa; Font-Bardia, Mercè; [et al.]. «Correction to "Structural Landscape of α-Acetamidocinnamic Acid Cocrystals with Bipyridine-Based Coformers: Influence of Crystal Packing on Their Thermal and Photophysical Properties"». Crystal Growth and Design, Vol. 24, Issue 7 (March 2024) https://doi.org/10.1021/acs.cgd.4c00270

Correcció de l'article: https://ddd.uab.cat/record/290898
DOI: 10.1021/acs.cgd.3c01374
PMID: 38405168

Article 20 p, 12.1 MB

Supporting information 28 p, 4.2 MB

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