Issue 58, 2018, Issue in Progress

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

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

Supplementary files

Article information

Article type
Paper
Submitted
10 Sep 2018
Accepted
18 Sep 2018
First published
26 Sep 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 33276-33290

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

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