Spontaneous assembly of silylethane-thiol derivatives on Au(111): a chemically robust thiol protecting group as the precursor for the direct formation of aromatic gold thiolate monolayers

Claude Niebel (1) , François Calard (1) , Thibaut Jarrosson (1) , Jean-Pierre Lère-Porte (1) , Tony Breton (2) , Françoise Serein-Spirau (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 MOLTECH-Anjou

Self-assembled monolayers (SAMs) on gold were obtained by the direct absorption of a fully conjugated phenylenethienylene derivative (4) presenting robust silylethane-thiol protecting groups as anchoring agents. The thiol deprotection and SAM formation have been evidenced by quartz crystal microbalance (QCM) measurements and X-ray photoelectron spectroscopy (XPS), and have been compared to the SAM obtained from its thioacetate analog (5). The chemically robust silylethane-thiol protecting group appeared as a surprisingly effective anchoring agent for the preparation of aromatic SAMs on Au(111), suitable for subsequent post-functionalization.

Mots clés: thiolate; thiol protecting group; monolayers

Domaines: Chimie organique; Matériaux

Claude Niebel, François Calard, Thibaut Jarrosson, Jean-Pierre Lère-Porte, Tony Breton, et al.. Spontaneous assembly of silylethane-thiol derivatives on Au(111): a chemically robust thiol protecting group as the precursor for the direct formation of aromatic gold thiolate monolayers. Chemical Communications, 2015, 51, pp.7622. ⟨10.1039/c5cc00600g⟩. ⟨hal-01144826⟩