Expanding the scope of diamond surface chemistry: Stille and sonogashira cross-coupling reactions

0512102 - FZÚ 2020 RIV US eng J - Journal Article
Raymakers, J. - Artemenko, Anna - Nicley, S. S. - Štenclová, Pavla - Kromka, Alexander - Haenen, K. - Maes, W. - Rezek, Bohuslav
Expanding the scope of diamond surface chemistry: Stille and sonogashira cross-coupling reactions.
Journal of Physical Chemistry C. Roč. 121, č. 42 (2017), s. 23446-23454. ISSN 1932-7447. E-ISSN 1932-7455
R&D Projects: GA ČR GA15-01809S
Institutional support: RVO:68378271
Keywords : functionalization * diamond * cross-coupling
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 4.484, year: 2017
Method of publishing: Limited access
https://doi.org/10.1021/acs.jpcc.7b06426

Well-defined covalent surface functionalization of diamond is a crucial, yet nontrivial, matter because of diamond’s intrinsic chemical inertness and stability. Herein, we demonstrate a two-step functionalization approach for H-terminated borondoped NCD films, which can lead to significant advances in the field of diamond hybrid photovoltaics. Primary diamond functionalization is performed via electrochemical diazonium grafting of in situ diazotized 4-iodoaniline. The freshly grafted iodophenyl functional moieties are then employed to couple a layer of thiophene molecules to the diamond surface via two well-established Pd-catalyzed cross-coupling reactions. XPS analysis indicates a dense coverage and successful cross-coupling. We find that the Stille reaction is accompanied by severe surface contamination, in spite of process optimization and thorough rinsing. Sonogashira cross-coupling provides a clean, high quality functionalization over a broad range of reaction conditions.

Permanent Link: http://hdl.handle.net/11104/0302684