title: Organogels based on J- and H-type aggregates of amphiphilic perylenetetracarboxylic diimides.
abstract: Three new perylenetetracarboxylic diimide (PDI) compounds substituted with hydrophobic and/or hydrophilic groups at the two imide nitrogen positions, namely N,N'-di[N-(4-aminophenyl)-3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide]-1,7-di(4-tert-butylphenoxy)perylene-3,4;9,10-tetracarboxylic diimide (1), N,N'-di[N-amido-3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide]-1,7-di(4-tert-butylphenoxy)perylene-3,4;9,10-tetracarboxylic diimide (2), and N-amido-3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide-N'-amido-3,4,5-tris(dodecyloxy)benzamide-1,7-di(4-tert-butylphenoxy)perylene-3,4;9,10-tetracarboxylate diimide (3), have been designed and prepared. The gelating abilities of them in different solvents have been investigated, and the results indicated that compounds 1 and 3 can form fluorescent gels whereas compound 2 cannot. The properties of the gels of compounds 1 and 3 have been investigated by UV-vis absorption and emission spectra. The results indicate that the gel of compound 1 is composed of H-aggregates, whereas the gel of compound 3 is composed of J-aggregates. The reversible transformation between gel and solution states induced by temperature change is observed. The structure of dried gel has been investigated by X-ray diffraction (XRD) experiments, and the morphology has been measured by atomic force microscopy (AFM). This research revealed successfully the crucial roles of amphiphilic properties and the side-chain conformations in controlling the gelating properties of PDI molecules. This information may be useful for the design of novel organogels based on perylenetetracarboxylic diimides.
authors.affiliation: Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, Department of Chemistry, Shandong University , Jinan, China 250100.
authors.forename: Haixia
authors.initials: H
authors.lastname: Wu
authors.forename: Lin
authors.initials: L
authors.lastname: Xue
authors.forename: Yan
authors.initials: Y
authors.lastname: Shi
authors.forename: Yanli
authors.initials: Y
authors.lastname: Chen
authors.forename: Xiyou
authors.initials: X
authors.lastname: Li