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Using “Threading Followed by Shrinking” to Synthesize Highly Stable Dialkylammonium-Ion-Based Rotaxanes

Authors

  • Liang-Yun Wang,

    1. Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617 (R.O.C.), Fax: (+886) 2-33661677
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  • Jia-Ling Ko,

    1. Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617 (R.O.C.), Fax: (+886) 2-33661677
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  • Prof. Chien-Chen Lai,

    1. Institute of Molecular Biology, National Chung Hsing University and Department of Medical Genetics, China Medical University Hospital, Taichung, Taiwan (R.O.C.)
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  • Yi-Hung Liu,

    1. Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617 (R.O.C.), Fax: (+886) 2-33661677
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  • Prof. Shie-Ming Peng,

    1. Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617 (R.O.C.), Fax: (+886) 2-33661677
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  • Prof. Sheng-Hsien Chiu

    Corresponding author
    1. Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617 (R.O.C.), Fax: (+886) 2-33661677
    • Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617 (R.O.C.), Fax: (+886) 2-33661677
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Abstract

Herein, we report a “threading followed by shrinking” approach for the synthesis of rotaxanes by using an “oxygen-deficient” macrocycle that contained two arylmethyl sulfone units and the dumbbell-shaped salt bis(3,5-dimethylbenzyl)ammonium tetrakis(3,5-trifluoromethylphenyl)borate as the host and guest components, respectively. The extrusion of SO2 from both of the arylmethyl sulfone units of the macrocyclic component in the corresponding [2]pseudorotaxane resulted in a [2]rotaxane that was sufficiently stable to maintain its molecular integrity in CD3SOCD3 at 393 K for at least 5 h.

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