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Title: Expanding the Scope of Diamond Surface Chemistry: Stille and Sonogashira Cross-Coupling Reactions
Authors: RAYMAKERS, Jorne 
Artemenko, Anna
NICLEY, Shannon 
Stenclova, Pavla
Kromka, Alexander
MAES, Wouter 
Rezek, Bohuslav
Issue Date: 2017
Source: 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.
Keywords: Chemistry, Physical; Nanoscience & Nanotechnology; Materials Science, Multidisciplinary
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ISSN: 1932-7447
e-ISSN: 1932-7455
DOI: 10.1021/acs.jpcc.7b06426
ISI #: 000414114800022
Rights: © 2017 American Chemical Society
Category: A1
Type: Journal Contribution
Validations: ecoom 2018
Appears in Collections:Research publications

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