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Anthracene and β-cyclodextrin-based semi-conducting rotaxanes: Effect of the benzylation on the physico-chemical and electrical properties

  • Teka, Safa
  • Jebnouni, Achref
  • Chemli, Mejed
  • Attia, Ghada
  • Baatout, Zeineb
  • Jaballah, Nejmeddine Smida
  • Ghorbel, Mouna
  • Majdoub, Mustapha
Publication Date
Oct 01, 2023
DOI: 10.1016/j.molstruc.2023.135802
OAI: oai:HAL:hal-04184117v1
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In this work, we report the benzylation of an anthracene and β-Cyclodextrin-based rotaxane. Then, a comparative study between the physicochemical and electrical properties of the modified rotaxane (R-Bn) and those of the pristine supramolecule (R) was conducted. We noted an important improvement of the solubility of the rotaxane following the o-benzylation of the β-Cyclodextrin hydroxyl groups. The analysis of the surface topography of the rotaxane films using atomic force microscopy (AFM) showed a smoother surface morphology for the supramolecular assembly R-Bn. Also, we have demonstrated that the introduction of benzyl moieties induces a remarkable broadening and a bathochromic shift of the UV–visible absorption and photoluminescence spectra, an improvement in the fluorescence yield as well as a reduction of the optical and electrochemical band gaps. In addition, a white photoluminescence was emitted from R-Bn thin layer while a blue emission was observed in the case of the primitive rotaxane film (R). Regarding the electrical measurements, the benzylation of the rotaxane induced a dramatic decrease of the threshold voltage (from 3.70 V to 1.55 V) and the dynamic resistances (from 113.84 kΩ to 11.51 kΩ), an important increase by one order of magnitude of the charge carrier mobility and a drastic increase of the conductivity by 5 orders of magnitude.

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