A competitive sensing system based on cyclobis(paraquat-p-phenylene) and a new β-cyclodextrin-tetrathiafulvalene derivative

Abstract

We report the synthesis of 4,5-di(ethylthio)-4′-[6-deoxy-β-cyclodextrin-6-yl-aminocarbonyl]-tetrathiafulvalene (β-CD-DET-TTF) and its inclusion abilities towards cyclobis(paraquat-p-phenylene) (CBPQT⁴⁺ ) and 1-naphthol. The structure of the synthesised compound has been established by mass spectrometry and ¹H NMR spectra combined with a theoretical MM3 and AM1 study. The sensor affords a charge transfer (CT) complex with the CBPQT⁴⁺  and is able to include 1-naphthol in the cyclodextrin cavity. The complexes were characterised experimentally by UV–vis spectroscopy and simulated by a MM3 docking procedure. The sensing ability of the β-CD-DET-TTF/CBPQT⁴⁺  complex towards 1-naphthol has been investigated by a competitive spectral method.

The synthesis and characterisation of a new water soluble β-CD-DET-TTF derivative able to formed a CT complex with the CBPQT⁴⁺  acceptor is reported. The water soluble CT complex β-CD-DET-TTF/CBPQT⁴⁺  could be used as an efficient sensor towards aromatic guests prone to give inclusion complexes with the CBPQT⁴⁺  ring.

Keywords:

• β-cyclodextrin
• tetrathiafulvalene
• cyclobis(paraquat-p-phenylene)
• charge transfer complex
• inclusion

Acknowledgements

The financial support from the CNRS, University of Angers and University of Dunkerque is gratefully acknowledged.