Triptycene-based self-assembled monolayer as a template for successive click reactions
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 poss...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
1 March 2023
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| In: |
The journal of physical chemistry. C, Energy, materials, and catalysis
Year: 2023, Volume: 127, Issue: 10, Pages: 5178-5185 |
| ISSN: | 1932-7455 |
| DOI: | 10.1021/acs.jpcc.3c00443 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.jpcc.3c00443
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| Author Notes: | Saunak Das, Fumitaka Ishiwari, Yoshiaki Shoji, Takanori Fukushima, and Michael Zharnikov |
| Summary: | 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. |
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| Item Description: | Gesehen am 19.04.2023 |
| Physical Description: | Online Resource |
| ISSN: | 1932-7455 |
| DOI: | 10.1021/acs.jpcc.3c00443 |