Aggregation Processes of Perylene Bisimide Diimidazolium Salts

The supramolecular aggregation of three diimidazolium‐functionalized perylene bisimides, differing in the alkyl chain length was investigated. These salts form aggregates in solvents like chloroform, dichloromethane, and glycerol. Solvent‐, concentration‐, and temperature‐dependent spectroscopic stu...

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Bibliographic Details
Published in:Chemistry : a European journal 2015-10, Vol.21 (42), p.14780-14790
Main Authors: D'Anna, Francesca, Marullo, Salvatore, Lazzara, Giuseppe, Vitale, Paola, Noto, Renato
Format: Article
Language:English
Subjects:
Agglomeration
Aggregates
aggregation
Chemistry
Chloroform
Elongated structure
Hydrogen bonding
imidazolium salts
Light scattering
perylene bisimides
Self assembly
Spectrum analysis
Stacking
supramolecular chemistry
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Summary:The supramolecular aggregation of three diimidazolium‐functionalized perylene bisimides, differing in the alkyl chain length was investigated. These salts form aggregates in solvents like chloroform, dichloromethane, and glycerol. Solvent‐, concentration‐, and temperature‐dependent spectroscopic studies were carried out, evidencing the occurrence of an isodesmic, enthalpy‐driven aggregation process, underpinned by π–π stacking and hydrogen bonding. Moreover, dynamic light scattering (DLS) measurements and SEM images revealed that these salts aggregate in chloroform into elongated structures. A tale of two tectons: The aim of this study was to conjugate the self‐assembly properties of imidazolium salts and perylene bisimides by studying the supramolecular aggregation of three diimidazolium‐functionalized perylene bisimides. It was found that these salts organize into large elongated structures by means of an isodesmic pathway, underpinned by π–π stacking and hydrogen bonding (see figure).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502240