Naslov
Perhalogenated hydroxyl aryl imines as halogen bond donors in cocrystals with nitrogen-containing acceptors

Autori
Baus Topić, Nea ; Cinčić, Dominik

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of Abstracts / - , 2023, 51-51

Skup
Twenty-ninth Slovenian-Croatian Crystallographic Meeting

Mjesto i datum
Topolšica, Slovenija, 14.06.2023. - 18.06.2023

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Podatak o recenziji nije dostupan

Ključne riječi
halogen bond ; cocrystal ; imine

Sažetak
During the past three decades, halogen bonding plays an increasingly prominent role in contemporary crystal engineering because it has been shown as an effective and predictable supramolecular “tool” [1]. It has been predominantly investigated in multicomponent crystals consisting of organic perhalogenated compounds as halogen bond donors and various organic and metal-organic compounds as halogen bond acceptors [2]. While many multicomponent systems contain imines as halogen bond acceptors [3], there are scarce examples of those that contain them as halogen bond donors [4]. In this work, we investigate the halogen bond donor potential of two novel peripherally perhalogenated imines prepared by condensation reaction of 2, 3, 5, 6-tetrafluoro-4-iodoaniline with salicylaldehyde (itfasal) or ortho-vanillin (itfaovan). The choice of the type of aldehyde allowed us to study the different supramolecular bonding capabilities of imines as well as their thermochromic behavior. Both imines were cocrystallized in 2:1 stoichiometric ratio with selected ditopic nitrogen-containing acceptors: 4, 4’-bipyridine (bpy), 1, 4- diazabicyclo[2.2.2]octane (dabco) and 1, 2-bis(4- pyridyl)ethane (bpean). Cocrystals were prepared by liquid-assisted grinding and crystallization from ethanol and were characterized by X-ray diffraction methods and by thermal analysis. Crystal structure determination of cocrystals revealed that all six cocrystals exhibit molecular trimers containing two imine molecules and one acceptor molecule interconnected by I···N halogen bonds. Solid-state thermochromic studies revealed that both imines and their cocrystals show reversible thermochromic behavior that is not accompanied by significant structural changes.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA