Expanding the Scope of Diamond Surface Chemistry - Stille and Sonogashira Cross-Coupling Reactions
At a Glance
Section titled āAt a Glanceā| Metadata | Details |
|---|---|
| Publication Date | 2017-10-06 |
| Journal | The Journal of Physical Chemistry C |
| Authors | Jorne Raymakers, Anna Artemenko, Shannon S. Nicley, Pavla Å tenclovĆ”, Alexander Kromka |
| Institutions | Czech Academy of Sciences, Institute of Physics, Czech Technical University in Prague |
| Citations | 19 |
Abstract
Section titled āAbstractāWell-defined covalent surface functionalization of diamond is a crucial, yet nontrivial, matter because of diamondās intrinsic chemical inertness and stability. Herein, we demonstrate a two-step functionalization approach for H-terminated boron doped diamond thin films, which can lead to significant advances in the field of diamond hybrid photovoltaics. Primary diamond surface 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, i.e., Stile and Sonogashira. X-ray photoelectron spectroscopy analysis indicates a dense coverage and successful cross-coupling in both cases. However, we find that the Stille reaction is generally accompanied by severe surface contamination, in spite of process optimization and thorough rinsing. Sonogashira cross-coupling on the other hand provides a clean, high quality functionalization over a broad range of reaction conditions. The protocols employing Sonogashira reactions thus appear to be the method of choice toward future fabrication of high-performance dye-functionalized diamond electrodes for photovoltaic applications.