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

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–...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-07, Vol.23 (40), p.9600-9606
Main Authors: Krishnan, Sumesh Babu, Gopidas, Karical Raman
Format: Article
Language:English
Subjects:
Absorption
Absorption spectra
Binding
Calorimetry
Charge transfer
Chemistry
Chirality
Cotton
Cyclodextrin
Cyclodextrins
Diimide
donor–acceptor systems
Fibers
Fluorescence
NMR
Nuclear magnetic resonance
Pyrene
supramolecular chemistry
Synergistic effect
Temperature dependence
Titration
Titration calorimetry
Twisting
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Summary: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).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201701123