Triptycene-Based Self-Assembled Monolayer as a Template for Successive Click Reactions

• Published in: Journal of physical chemistry. C Vol. 127; no. 10; pp. 5178 - 5185
• Main Authors: Das, Saunak, Ishiwari, Fumitaka, Shoji, Yoshiaki, Fukushima, Takanori, Zharnikov, Michael
• Format: Journal Article
• Language: English
• Published: American Chemical Society 16.03.2023
• Subjects: C: Physical Properties of Materials and Interfaces
• ISSN: 1932-7447; 1932-7455
• DOI: 10.1021/acs.jpcc.3c00443

Triptycene-based molecules represent a promising platform for tripodal monomolecular assembly on solid substrates. The versatility of the approach can be increased significantly if a decoration of the assembled tripods by purpose-specific functional groups will be possible. In this context, the possibility of click reaction between the 10-ethynyl-substituted 1,8,13-trimercaptomethyltriptycene monolayer (EtTripS) on Au(111) and an azide-decorated substituent is tested and additionally verified by a subsequent derivatization reaction. The primary monolayer is shown to exhibit dense molecular packing, tripodal adsorption geometry, and high orientational order, which qualify it well as a template for subsequent reactions. The characteristic spectroscopic fingerprints of the click and derivatization reactions were recorded. The overall impact of these reactions on the work function of the EtTripS-engineered substrateused as a measure of their efficiency and as an example of functional propertieswas well comparable with the effect of the analogous substitution (−CF3) for monodentate monolayers, emphasizing the high potential of the on-surface modification approach.