Organogelators based on iodo 1,2,3-triazole functionalized with coumarin: properties and gelator-solvent interaction

• Published in: Tetrahedron Vol. 71; no. 14; pp. 2124 - 2133
• Main Authors: Huang, Yaodong, Zhang, Yan, Yuan, Yuqin, Cao, Wenwen
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.04.2015; Elsevier
• Subjects: absorption; chemical structure; Chemistry; Chemistry, Organic; Coumarin; Cyclo-addition; cycloaddition reactions; fluorescence emission spectroscopy; gelation; gels; mercury; new family; nuclear magnetic resonance spectroscopy; Organogelator; photochemistry; Physical Sciences; scanning electron microscopy; Science & Technology; Self-assemble; solubility; Solvent effects; solvents; stereochemistry; ultraviolet-visible spectroscopy; van der Waals forces; X-ray diffraction; Organogelator; Cyclo-addition; Coumarin; Self-assemble; Solvent effects; HANSEN SOLUBILITY PARAMETERS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2015.02.044

A new family of 1,2,3-triazole derivatives containing coumarin functional group with different alkyl chain lengths was synthesized and their gelation abilities and photochemistry properties were fully characterized. The main force for the self-assembly in gel state are π-π stacking and van der Waals interaction. Solubility parameters and Teas plots of the gelator and several single solvents were calculated to estimate the gelator-solvent interaction. The organogel in a binary solvent system was also characterized using various microscopic techniques including X-ray diffraction (XRD), scanning electron microscopy (SEM) and UV–vis. Reversible and stereoselective [2+2] cyclo-addition of the gel was confirmed by 1H NMR, UV absorption, fluorescence spectra and SEM. The gels formed were affected and destroyed by the addition of mercury ion. [Display omitted]