Aggregation Processes of Perylene Bisimide Diimidazolium Salts

Abstract

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.

Impact of subtle change in branched amino acid on the assembly and properties of perylene bisimides hydrogels

“…21,22 They have also shown n-type semiconductor behavior and have good photoconductivity, due to their high light absorptivity and ability to readily form a radical anion making them interesting materials for OPVs. [23][24][25] Properties of the PBIs such as solubility, 26 electrical, 27,28 and colour, 29 can be modified through chemical structure changes, whilst self-assembly of PBIs can be modified using environmental stimulus such as solvent, 30 concentration 31 or temperature. 17 The structures of PBIs can be modified at three main positions, the bay, ortho and imide position.…”

Aggregation Behavior and Electron‐Transfer Reaction of Dendritic Perylene Bisimide, Accompanied by the Formation of Highly Stable Anionic Radical Species

“…Further increasing the organic solvent content decreased the PEPBI fluorescence (Figure S6 d). It has been reported that the process of PBI aggregation is underpinned by both π–π stacking and hydrogen bonding, which was demonstrated by solvent‐dependent spectroscopic investigation …”

Morphogenesis and Optoelectronic Properties of Supramolecular Assemblies of Chiral Perylene Diimides in a Binary Solvent System

“…From the spectra, we calculated the degree of aggregation ( α agg ), which is the fraction of molecules present in the aggregates by using the [Eq. (2)] 39 :where I i is the emission intensity at a given composition, I 0 the emission intensity detected in pure THF, and I 100 is the emission intensity measured in pure water. Then we plotted α agg as a function of the amount of water present in the solvent mixture.…”