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Guest-responsive structural adaptation of a rationally-designed molecular tweezer based on Tröger’s base

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Abstract

We have designed and synthesized a modified Tröger’s base TB in which the sterically-rigidified aryl rings that protrude into its groove were envisaged to preclude self-inclusion. From a limited preliminary experimentation, TB has been found to exhibit guest inclusion. The X-ray determined structures of the crystals of guest-free TB and its inclusion compounds with acetonitrile and o-dichlorobenzene reveal remarkable adaptability of the TB core to undergo subtle structural changes in response to the guest that is included. The structural analyses demonstrate the fact that TB behaves like a molecular tweezer.

X-ray determined crystal structures of the guest-free Tröger’s Base derivative (TB) and its inclusion compounds with acetonitrile and o-dichlorobenzene reveal that TB functions like a molecular tweezer with remarkable adaptability to undergo subtle structural changes in response to the guest that is included.

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Acknowledgements

JNM is thankful to SERB (DST) for generous financial support. IN and AB are grateful to CSIR for their senior research fellowships.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208 016, India

    ISHITA NEOGI, ALANKRITI BAJPAI & JARUGU NARASIMHA MOORTHY

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  1. ISHITA NEOGI
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  2. ALANKRITI BAJPAI
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  3. JARUGU NARASIMHA MOORTHY
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Correspondence to JARUGU NARASIMHA MOORTHY.

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Supplementary Information

The 1H NMR spectra of the crystals of the inclusion compounds in CDCl3 and TGA profiles. The electronic supporting information can be seen at www.ias.ac.in/chemsci.

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NEOGI, I., BAJPAI, A. & MOORTHY, J.N. Guest-responsive structural adaptation of a rationally-designed molecular tweezer based on Tröger’s base. J Chem Sci 126, 1323–1329 (2014). https://doi.org/10.1007/s12039-014-0708-7

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