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

0494133 - ÚFCH JH 2019 RIV GB eng J - Journal Article
Raymakers, J. - Krýsová, Hana - Artemenko, Anna - Čermák, Jan - Nicley, S. S. - Verstappen, P. - Gielen, S. - Kromka, Alexander - Haenen, K. - Kavan, Ladislav - Maes, W. - Rezek, Bohuslav
Functionalization of boron-doped diamond with a push–pull chromophore via Sonogashira and CuAAC chemistry.
RSC Advances. Roč. 8, č. 58 (2018), s. 33276-33290. E-ISSN 2046-2069
R&D Projects: GA ČR GA13-31783S; GA ČR GA15-01809S; GA MŠMT(CZ) EF15_003/0000464
Institutional support: RVO:61388955 ; RVO:68378271
Keywords : boron-doped diamond * cooper compounds * dye-sensitized solar cells
OECD category: Physical chemistry; Condensed matter physics (including formerly solid state physics, supercond.) (FZU-D)
Impact factor: 3.049, year: 2018
Method of publishing: Open access

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.

Permanent Link: http://hdl.handle.net/11104/0287393