Jump to main content
Jump to site search

Issue 58, 2018, Issue in Progress
Previous Article Next Article

Functionalization of boron-doped diamond with a push–pull chromophore via Sonogashira and CuAAC chemistry

Author affiliations

Abstract

Improving the performance of p-type photoelectrodes represents a key challenge toward significant advancement in the field of tandem dye-sensitized solar cells. Herein, we demonstrate the application of boron-doped nanocrystalline diamond (B:NCD) thin films, covalently functionalized with a dithienopyrrole–benzothiadiazole push–pull chromophore, as alternative photocathodes. First, a primary functional handle is introduced on H-terminated diamond via electrochemical diazonium grafting. Afterwards, Sonogashira cross-coupling and Cu(I) catalyzed azide–alkyne cycloaddition (CuAAC) reactions are employed to attach the chromophore, enabling the comparison of the degree of surface functionalization and the importance of the employed linker at the diamond-dye interface. X-ray photoelectron spectroscopy shows that surface functionalization via CuAAC results in a slightly higher chromophore coverage compared to the Sonogashira cross-coupling. However, photocurrents and photovoltages, obtained by photoelectrochemical and Kelvin probe measurements, are approximately three times larger on photocathodes functionalized via Sonogashira cross-coupling. Surface functionalization via Sonogashira cross-coupling is thus considered the preferential method for the development of diamond-based hybrid photovoltaics.

Graphical abstract: Functionalization of boron-doped diamond with a push–pull chromophore via Sonogashira and CuAAC chemistry

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Sep 2018, accepted on 18 Sep 2018 and first published on 26 Sep 2018


Article type: Paper
DOI: 10.1039/C8RA07545J
RSC Adv., 2018,8, 33276-33290
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Functionalization of boron-doped diamond with a push–pull chromophore via Sonogashira and CuAAC chemistry

    J. Raymakers, H. Krysova, A. Artemenko, J. Čermák, S. S. Nicley, P. Verstappen, S. Gielen, A. Kromka, K. Haenen, L. Kavan, W. Maes and B. Rezek, RSC Adv., 2018, 8, 33276
    DOI: 10.1039/C8RA07545J

    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