DataVXACS Applied Materials & InterfacesPaper
journal article·2020-02-05Open access

Tetrapodal Diazatriptycene Enforces Orthogonal Orientation in Self-Assembled Monolayers

Frank S. Benneckendorf, Valentina Rohnacher, Eric Sauter, Sabina Hillebrandt, Maybritt Münch, Can Wang, Stefano Casalini, Katharina Ihrig, Sebastian Beck, Daniel Jänsch, Jan Freudenberg, Wolfram Jaegermann, Paolo Samorì, Annemarie Pucci, Uwe H. F. Bunz, Michael Zharnikov, Klaus Müllen

ACS Applied Materials & Interfaces· Volume 12· Issue 5
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Source abstract

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.
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Research context

OpenAlex topics: Molecular Junctions and Nanostructures · Quantum Dots Synthesis And Properties · Advanced biosensing and bioanalysis techniques

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

InnovationLab, Speyerer Straße 4, 69115 Heidelberg, Germany

Kirchhoff-Institut für Physik, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 227, 69120 Heidelberg, Germany

Angewandte Physikalische Chemie, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 253, 69120 Heidelberg, Germany

Organic Semiconductor Centre, SUPA, School of Physics and Astronomy, University of St Andrews, North Haugh, St Andrews KY16 9SS, United Kingdom

Materials Science Department, Surface Science Division, TU Darmstadt, Otto-Berndt-Straße 3, 64287 Darmstadt, Germany

University of Strasbourg, CNRS, ISIS, 8 allée Gaspard Monge, 67000 Strasbourg, France

Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany

Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany

Funding

Agence Nationale de la Recherche · Bundesministerium für Bildung und Forschung · Deutsche Forschungsgemeinschaft

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