Synthesis of Functionalized Mono-, Bis-, and Trisethynyltriptycenes for One-Dimensional Self-Assembly on Surfaces

Abstract

This paper describes the synthesis of triptycene-based building blocks that are able to interact through hydrogen bonds to form one-dimensional self-assembled motifs on surfaces. We designed 9,10-diethynyltriptycene derivatives functionalized at the ethynyl end groups by a variety of hydrogen-bonding groups for homomolecular recognition and complementary building blocks for heteromolecular recognition. We also present the synthesis of bis- and trisethynyltriptycenes with terminal alkyne functional groups available for on-surface azide-alkyne cycloaddition reaction to expand the potential of the triptycene building block.

Keywords: Sonogashira coupling; alkynes; anthracenes; hydrogen bonds; triptycenes.