Anti-cooperative supramolecular polymerization: a new K₂-K model applied to the self-assembly of perylene bisimide dye proceeding via well-defined hydrogen-bonded dimers.

ABSTRACT: A perylene bisimide dye bearing amide functionalities at the imide positions derived from amino acid l-alanine and a dialkoxy-substituted benzyl amine self-assembles into tightly bound dimers by ?-?-stacking and hydrogen bonding in chloroform. In less polar or unpolar solvents like toluene and methylcyclohexane, and in their mixtures, these dimers further self-assemble into extended oligomeric aggregates in an anti-cooperative process in which even numbered aggregates are highly favoured. The stepwise transition from dimers into oligomers can not be properly described by conventional K₂-K model, and thus a new K₂-K aggregation model has been developed, which interpretes the present anti-cooperative supramolecular polymerization more appropriately. The newly developed K₂-K model will be useful to describe self-assembly processes of a plethora of other ?-conjugated molecules that are characterized by a favored dimer species.

SUBMITTER: Gershberg J 

PROVIDER: S-EPMC5582317 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature