Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Observation of Supramolecular Chirality in a Hierarchically Self-Assembled Mixed-Stack Charge-Transfer Complex

Observation of Supramolecular Chirality in a Hierarchically Self-Assembled Mixed-Stack Charge-Transfer Complex
Karical Raman Gopidas, Sumesh Babu Krishnan
Supramolecular chirality was observed in a charge-transfer (CT) complex formed by self-assembly of β-cyclodextrin-linked pyrene and adamantane-linked pyromellitic diimide in water. In the complex, the pyrene–pyromellitic diimide CT interaction is reinforced several-fold by the strong β-cyclodextrin–adamantane inclusion binding interaction, as confirmed by 1H NMR, absorption, fluorescence and isothermal titration calorimetry studies. The CT complex exhibited high stability, as inferred from the temperature-dependent absorption and NMR studies. The CT absorption band exhibited a positive Cotton effect indicative of supramolecular chirality for the complex. Twisted fibres were observed in TEM, AFM, and SEM experiments. A mechanism involving synergistic binding interactions leading to 2D sheets, followed by twisting of the sheet, is proposed for the formation of twisted fibres. This system offers a chance to investigate a combination of supramolecular CT and supramolecular chirality and explore their synergistic effects. Do the twist: A chiral supramolecular charge-transfer complex is formed by the synergistic effect of charge-transfer interaction and inclusion binding between a pyrene-appended β-cyclodextrin donor and an adamantane-linked pyromellitic diimide acceptor in aqueous solution, and formation of twisted fibres was observed by electron microscopy and AFM (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701123

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