Solvent-dependent self-assembly of N-annulated perylene diimides. From dimers to supramolecular polymers.

ABSTRACT: The synthesis and self-assembling features of the N-annulated perylene diimide (NPBI) 1 in different solvents are reported. Compound 1 possesses two chiral linkers, derived from (S)-(+)-alaninol, that connect the central aromatic NPBI segment and the peripheral trialkoxybenzamide units. The Ala-based linker has been demonstrated to strongly favor the formation of intramolecularly H-bonded seven-membered pseudocycles. NPBI 1 shows a strong tendency to self-assemble even in a good solvent like CHCl₃ and the formation of chiral dimers is detected in this good solvent. Both experimental techniques and theoretical calculations reveal that the intramolecular H-bonded pseudocycles are very robust and the formation of chiral dimers is driven by the π-stacking of two units

SUBMITTER: Naranjo C 

PROVIDER: S-EPMC10510848 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature