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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/25557

Title: Expanding the Scope of Diamond Surface Chemistry: Stille and Sonogashira Cross-Coupling Reactions
Authors: Raymakers, Jorne
Artemenko, Anna
Nicley, Shannon S.
Stenclova, Pavla
Kromka, Alexander
Haenen, Ken
Maes, Wouter
Rezek, Bohuslav
Issue Date: 2017
Citation: JOURNAL OF PHYSICAL CHEMISTRY C, 121(42), p. 23446-23454
Abstract: 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 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.
Notes: [Raymakers, Jorne; Nicley, Shannon S.; Haenen, Ken; Maes, Wouter] UHasselt Hasselt Univ, Inst Mat Res IMO, B-3590 Diepenbeek, Belgium. [Raymakers, Jorne; Nicley, Shannon S.; Haenen, Ken; Maes, Wouter] IMOMEC, IMEC VZW, B-3590 Diepenbeek, Belgium. [Artemenko, Anna; Stenclova, Pavla; Kromka, Alexander; Rezek, Bohuslav] Czech Acad Sci, Inst Phys, Cukrovarnicka 10, Prague 16200 6, Czech Republic. [Rezek, Bohuslav] Czech Tech Univ, Fac Elect Engn, Tech 2, Prague 16625 6, Czech Republic.
URI: http://hdl.handle.net/1942/25557
DOI: 10.1021/acs.jpcc.7b06426
ISI #: 000414114800022
ISSN: 1932-7447
Category: A1
Type: Journal Contribution
Validation: ecoom, 2018
Appears in Collections: Research publications

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