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, 6 (8), 4828-4836

Synthesis of Triazolium-Based Mono- And Tris-Branched [1]rotaxanes Using a Molecular Transporter of dibenzo-24-crown-8

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Synthesis of Triazolium-Based Mono- And Tris-Branched [1]rotaxanes Using a Molecular Transporter of dibenzo-24-crown-8

P Waelès et al. Chem Sci.

Abstract

We report a diverted route to [1]rotaxane and tris-branched [1]rotaxane that are devoid of any efficient template and which could not be obtained by classical straightforward strategies. The described chemical route relies on the utilization of a "macrocycle transporter", which is able first to bind a macrocycle, second to link temporarily a triazolium-containing molecular axle, and third to deliver the macrocycle around the new docked axle through molecular machinery in a [1]rotaxane structure. The extended encircled thread is eventually cleaved by an amine or a triamine to afford the triazolium-containing [1]rotaxanes, releasing at the same time, the macrocycle transporter as a recyclable species.

Figures

Fig. 1
Fig. 1. Chemical templated routes to [1]rotaxanes.
Fig. 2
Fig. 2. Synthesized [1]rotaxanes 6 and 7 with atom assignments.
Fig. 3
Fig. 3. A novel route to [1]rotaxane F based on a recyclable macrocycle transporter A.
Scheme 1
Scheme 1. Preparation of mono- and tris-branched triazolium-containing [1]rotaxanes using the recyclable macrocycle transporter 1.
Fig. 4
Fig. 4. 1H NMR Spectra (600 MHz, 298 K) of (a) the non-interlocked analogue 4u in CD3CN, (b) the loosened [1]rotaxane 4l in CD3CN, (c) the loosened and tightened [1]rotaxanes 4l and 4t in DMSO-d 6 at t = 20 h, (d) the [1]rotaxane 4l in DMSO-d 6 at t = 0 h and (e) the non-interlocked analogue 4u in DMSO-d 6. The numbering and colorings correspond to the hydrogen assignments indicated in Scheme 1.
Fig. 5
Fig. 5. 1H NMR Spectra (600 MHz, CD3CN, 298 K) of (a) the non-interlocked analogue 4u, (b) the loosened [1]rotaxane 4l, (c) the N-carbamoylated tightened [1]rotaxane 5 and (d) the non-interlocked analogue 5u. The numbering and colorings correspond to the hydrogen assignments indicated in Scheme 1.
Fig. 6
Fig. 6. 1H NMR Spectra (600 MHz, CD3CN, 298 K) of (a) the non-interlocked analogue 6u and (b) triazolium-containing [1]rotaxane 6. The numbering and colorings correspond to the hydrogen assignments indicated in Fig. 2.
Fig. 7
Fig. 7. 1H NMR Spectra (600 MHz, CD3CN, 298 K) of (a) the non-interlocked analogue 7u and (b) triazolium-containing [1]rotaxane 7. The numbering and colorings correspond to the hydrogen assignments indicated in Fig. 2.

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