Stimuli-Responsive Self-Assembly of a Naphthalene Diimide by Orthogonal Hydrogen Bonding and Its Coassembly with a Pyrene Derivative by a Pseudo-Intramolecular Charge-Transfer Interaction

Authors

  • Anindita Das,

    1. Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Kolkata, 700032 (India)
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  • Dr. Suhrit Ghosh

    Corresponding author
    1. Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Kolkata, 700032 (India)
    • Polymer Science Unit, Indian Association for the Cultivation of Science, 2A and 2B Raja S. C. Mullick Road, Kolkata, 700032 (India)

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  • We thank Haridas Kar for providing compound 2. A.D. thanks the CSIR, New Delhi, India for a research fellowship. S.G. thanks the SERB, India for funding (SR/S1/OC-18/2012).

Abstract

A naphthalene diimide (NDI) building block containing hydrazide (H1) and hydroxy (H2) groups self-assembled into a reverse-vesicular structure in methylcyclohexane by orthogonal H-bonding and π-stacking. At an elevated temperature (LCST=43 °C), destruction of the assembled structure owing to selective dissociation of H2–H2 H bonding led to macroscopic precipitation. Further heating resulted in homogeneous redispersion of the sample at 70 °C (UCST) and the formation of a reverse-micellar structure. In the presence of a pyridine (H3)-functionalized pyrene (PY) donor, a supramolecular dyad (NDI–PY) was formed by H2–H3 H-bonding. Slow transformation into an alternate NDI–PY stack occurred by a folding process due to the charge-transfer interaction between NDI and PY. The mixed NDI–PY assembly exhibited a morphology transition from a reverse micelle (with a NDI–PY mixed-stack core) below the LCST to another reverse micelle (with a NDI core) above the UCST via a “denatured” intermediate.

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