Naslov
Gelation Ability of Novel Oxalamide-based Derivatives Bearing a Stilbene as a Photo-responsive Unit

Autori
Miljanić, Snežana ; Frkanec, Leo ; Meić, Zlatko ; Žinić, Mladen

Izvornik
European journal of organic chemistry (1434-193X) 2006 (2006), 5; 1323-1334

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Gelation; Isomers; Oxalamide; Self-assembly; Stilbene

Sažetak
Oxalamide-based derivatives containing one or two oxalyl amide moieties coupled to 4 or 4, 4’ positions of cis- and trans-stilbene were synthesized. In order to modulate the solvent gelation tendencies, a series of derivatives with modified terminal functions were prepared. The trans-stilbene dioxalamide-based derivatives were sparingly soluble or insoluble in water and in organic solvents, whereas the trans-stilbene monooxalamide-based derivatives were soluble in most organic solvents. Incorporation of a C12 alkyl chain in the structure of the latter compounds resulted in a decreased solubility but in an increased gelation tendency of the substances. The ethyl ester oxalamide-based derivative trans-3a and the amino acid oxalamide-based derivative trans-3e acted as efficient gelators of various organic solvents. In contrast, cis-3a showed a poor gelation ability or none at all, owing to its good solubility. Considering the difference in gelation abilities of the compounds trans-3a and cis-3a and the photo-responsive conformational changes of the stilbene part of the molecule, a controlled gelation by light was achieved. FT-IR and 1H NMR spectroscopic measurements supported the view that the hydrogen bonding between oxalamide fragments played an important role in gel formation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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