Tetrapodal diazatriptycene enforces orthogonal orientation in self-assembled monolayers

Frank S. Benneckendorf, Valentina Rohnacher, Eric Sauter, Sabina Hillebrandt, Maybritt Muench, Can Wang, Stefano Casalini, Katharina Ihrig, Sebastian Beck, Daniel Jaensch, Jan Freudenberg, Wolfram Jaegermann, Paolo Samori, Annemarie Pucci, Uwe H. F. Bunz, Michael Zharnikov, Klaus Muellen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Conformationally rigid multipodal molecules should control the orientation and packing density of functional head groups upon self-assembly on solid supports. Common tripods frequently fail in this regard because of inhomogeneous bonding configuration and stochastic orientation. These issues are circumvented by a suitable tetrapodal diazatriptycene moiety, bearing four thiol-anchoring groups, as demonstrated in the present study. Such molecules form well-defined self-assembled monolayers (SAMs) on Au(111) substrates, whereby the tetrapodal scaffold enforces a nearly upright orientation of the terminal head group with respect to the substrate, with at least three of the four anchoring groups providing thiolate-like covalent attachment to the surface. Functionalization by condensation chemistry allows a large variety of functional head groups to be introduced to the tetrapod, paving the path toward advanced surface engineering and sensor fabrication.Functionalization by condensation chemistry allows a large variety of functional head groups to be introduced to the tetrapod, paving the path toward advanced surface engineering and sensor fabrication.

Original languageEnglish
Pages (from-to)6565-6572
Number of pages8
JournalACS Applied Materials & Interfaces
Volume12
Issue number5
Early online date11 Dec 2019
DOIs
Publication statusPublished - 5 Feb 2020

Keywords

  • Self-assembled monolayers
  • Orthogonal orientation
  • Dipole
  • Triptycene
  • Surface modification
  • Platform
  • Tetrapod

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