Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

Jun Terao,
Yohei Konoshima,
Akitoshi Matono,
Hiroshi Masai,
Tetsuaki Fujihara and
Yasushi Tsuji

Letter
Published 28 Nov 2014

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1. Graphical Abstract
2. Figure 1: Synthesis of [1]rotaxane by self-inclusion of a host–guest-linked molecule: a) short molecular leng...
  
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3. Figure 2: Synthesis of an insulated molecule via flipping phenomenon.
  
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4. Scheme 1: The synthetic route to the PMβ-CD based linked [3]rotaxane with a 5,15-di([1,1'-biphenyl]-4-yl)porp...
  
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5. Figure 3: The aromatic region of the ¹H NMR spectra of 5 at 25 °C: 1) CDCl₃, 2) CD₃OD, and 3) CD₃OD:D₂O 1:1.
  
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6. Scheme 2: Selective synthesis of fixed [3]rotaxane by Suzuki cross-coupling reaction.
  
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7. Scheme 3: The synthetic routes to precursor of PM β-CD based insulated oligothiophene.
  
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8. Scheme 4: Synthesis of dibromohexa(para-phenylene) with two PMCDs 20.
  
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9. Scheme 5: Synthesis of pseudo-linked [3]rotaxanes via double self-inclusion through flipping.
  
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10. Figure 4: The aromatic region of the ¹H NMR spectra of 5 at 25 °C: 1) CDCl₃, 2) CD₃OD, and CD₃OD/D₂O 1:1.
  
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11. Figure 5: The aromatic region of the ¹H NMR spectra of 20 at 25 °C: 1) CDCl₃, 2) CD₃OD, and CD₃OD/D₂O 1:1.
  
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12. Scheme 6: Synthesis of fixed [3]rotaxane via complexation with rhodium porphyrin.
  
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13. Figure 6: Partial ROESY NMR spectrum of 26 (400 MHz, CDCl₃) showing the NOEs between aromatic protons of the ...
  
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