Expanding the Scope of Diamond Surface Chemistry: Stille and Sonogashira Cross-Coupling Reactions

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68407700%3A21230%2F17%3A00315078" target="_blank" >RIV/68407700:21230/17:00315078 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/68378271:_____/17:00512102

Výsledek na webu

<a href="http://dx.doi.org/10.1021/acs.jpcc.7b06426" target="_blank" >http://dx.doi.org/10.1021/acs.jpcc.7b06426</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jpcc.7b06426" target="_blank" >10.1021/acs.jpcc.7b06426</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Expanding the Scope of Diamond Surface Chemistry: Stille and Sonogashira Cross-Coupling Reactions

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Expanding the Scope of Diamond Surface Chemistry: Stille and Sonogashira Cross-Coupling Reactions

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Physical Chemistry C

ISSN

1932-7447

e-ISSN

—

Svazek periodika

121

Číslo periodika v rámci svazku

42

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

23446-23454

Kód UT WoS článku

000414114800022

EID výsledku v databázi Scopus

2-s2.0-85032744815