Distance Matters: Biasing Mechanism, Transfer of Asymmetry, and Stereomutation in N-Annulated Perylene Bisimide Supramolecular Polymers
نویسندگان
چکیده
The synthesis of two series N-annulated perylene bisimides (PBIs), compounds 1 and 2, is reported, their self-assembling features are thoroughly investigated by a complete set spectroscopic measurements theoretical calculations. study corroborates the enormous influence that distance between PBI core peripheral groups exerts on chiroptical properties supramolecular polymerization mechanism. Compounds 1, with separated from central methylenes an ester group, form J-type polymers in cooperative manner but exhibit negligible properties. lack clear helicity, due to staircase arrangement units aggregate, justifies these features. In contrast, attaching directly drastically changes which H-type aggregates following isodesmic These show strong aggregation-caused quenching (ACQ) effect leads nonemissive aggregates. Chiral (S)-2 (R)-2 experience efficient transfer asymmetry afford P- M-type aggregates, respectively, although no amplification achieved majority rules or “sergeants-and-soldiers” experiments. A solvent-controlled stereomutation observed for chiral (R)-2, helical different handedness depending solvent (methylcyclohexane toluene). accounted considering possible conformations terminal phenyl groups, eclipsed staggered, lead linear self-assemblies, relative stabilities solvent.
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2021
ISSN: ['0002-7863', '1520-5126', '1943-2984']
DOI: https://doi.org/10.1021/jacs.1c06125