Jump to main content
Jump to site search

Issue 65, 2017
Previous Article Next Article

Synthesis and characterization of fluorophthalocyanines bearing four 2-(2-thienyl)ethoxy moieties: from the optimization of the fluorine substitution to chemosensing

Author affiliations

Abstract

The energy levels of the HOMO/LUMO Frontier orbitals and the electronic properties of phthalocyanine macrocycles can be tuned by the introduction of substituents. Starting from tetrafluorophthalonitrile, we studied the substitution of fluorine atoms by (2-thienyl)ethoxy moieties. An optimization of the experimental conditions (nature and stoichiometry of the alcohol and base, temperature) allowed us to obtain the monoalkoxy derivative with a very good yield. It was fully characterized using 19F and 1H NMR spectroscopies, thermal analysis and X-ray diffraction on single crystals. Then, the corresponding zinc phthalocyanine was synthesized, characterized by means of 19F and 1H NMR spectroscopies, thermal analysis, and also by electronic spectroscopy and electrospray mass spectrometry. The unsymmetrical zinc phthalocyanine bearing also four (2-thienyl)ethoxy moieties was prepared by the mixed condensation of the tetraalkoxyphthalonitrile with the tetrafluorophthalonitrile. The phthalocyanines were used to build an electronic device, a p-type Molecular Semiconductor – Doped Insulator heterojunction (MSDI), in combination with the lutetium bisphthalocyanine as a molecular semiconductor, and their chemosensing behavior towards ammonia was studied.

Graphical abstract: Synthesis and characterization of fluorophthalocyanines bearing four 2-(2-thienyl)ethoxy moieties: from the optimization of the fluorine substitution to chemosensing

Back to tab navigation

Supplementary files

Publication details

The article was received on 11 May 2017, accepted on 11 Aug 2017 and first published on 23 Aug 2017


Article type: Paper
DOI: 10.1039/C7RA05325H
RSC Adv., 2017,7, 41272-41281
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Synthesis and characterization of fluorophthalocyanines bearing four 2-(2-thienyl)ethoxy moieties: from the optimization of the fluorine substitution to chemosensing

    A. Wannebroucq, R. Meunier-Prest, J. Chambron, C. Brachais, J. Suisse and M. Bouvet, RSC Adv., 2017, 7, 41272
    DOI: 10.1039/C7RA05325H

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements