New semi-conducting rotaxane based on β-cyclodextrin and anthracene moieties

Safa Teka, Khaled Hriz, Nejmeddine Jaballah, David Kreher, Fabrice Dominique Mathevet, Nathalie Jarroux, Mustapha Majdoub

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A new rotaxane (BPAAn/β-CD), consisting of an anthracene-based semi-conducting material (BPAAn) encapsulated into β-cyclodextrin (β-CD), has been synthesized via the Williamson reaction in solvent-free conditions. The supramolecular structure of the compound was confirmed by NMR and FT-IR spectroscopies. The optical and morphological properties of this organic material were investigated by UV-visible absorption, photoluminescence spectroscopy and atomic force microscopy. BPAAn/β-CD film has an optical gap of 2.9 eV and exhibits green photoluminescence. An optical gap of 2.9 eV was estimated from the absorption edge of the rotaxane thin film. The BPAAn/β-CD exhibits a blue photoluminescence in dilute solution; whereas, a green emission was observed in the solid state, due to the π-π interaction in the anthracene moieties. The rotaxane shows a significantly enhanced PL quantum yield and improved film quality in comparison with the free BPAAn. The HOMO and LUMO levels were estimated using cyclic voltammetry analysis, and show enhanced electron affinity of the BPAAn in its complexed form. A single-layer device with the configuration [ITO/rotaxane/Aluminum] has been elaborated and showed low turn-on voltage of 5 V.

Original languageEnglish
Pages (from-to)189-197
Number of pages9
JournalMaterials Science in Semiconductor Processing
Volume34
DOIs
Publication statusPublished - Jan 1 2015

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Rotaxanes
Anthracene
Cyclodextrins
anthracene
Photoluminescence
photoluminescence
conduction
Electron affinity
Photoluminescence spectroscopy
Quantum yield
Cyclic voltammetry
Infrared spectroscopy
Atomic force microscopy
Nuclear magnetic resonance
organic materials
electron affinity
ITO (semiconductors)
Aluminum
Thin films
spectroscopy

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics
  • Mechanics of Materials
  • Mechanical Engineering

Cite this

Teka, S., Hriz, K., Jaballah, N., Kreher, D., Mathevet, F. D., Jarroux, N., & Majdoub, M. (2015). New semi-conducting rotaxane based on β-cyclodextrin and anthracene moieties. Materials Science in Semiconductor Processing, 34, 189-197. https://doi.org/10.1016/j.mssp.2015.01.051

New semi-conducting rotaxane based on β-cyclodextrin and anthracene moieties. / Teka, Safa; Hriz, Khaled; Jaballah, Nejmeddine; Kreher, David; Mathevet, Fabrice Dominique; Jarroux, Nathalie; Majdoub, Mustapha.

In: Materials Science in Semiconductor Processing, Vol. 34, 01.01.2015, p. 189-197.

Research output: Contribution to journalArticle

Teka, S, Hriz, K, Jaballah, N, Kreher, D, Mathevet, FD, Jarroux, N & Majdoub, M 2015, 'New semi-conducting rotaxane based on β-cyclodextrin and anthracene moieties', Materials Science in Semiconductor Processing, vol. 34, pp. 189-197. https://doi.org/10.1016/j.mssp.2015.01.051
Teka, Safa ; Hriz, Khaled ; Jaballah, Nejmeddine ; Kreher, David ; Mathevet, Fabrice Dominique ; Jarroux, Nathalie ; Majdoub, Mustapha. / New semi-conducting rotaxane based on β-cyclodextrin and anthracene moieties. In: Materials Science in Semiconductor Processing. 2015 ; Vol. 34. pp. 189-197.
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