Stepwise Adsorption of Alkoxy‐Pyrene Derivatives onto a Lamellar, Non‐Porous Naphthalenediimide‐Template on HOPG

Abstract

The development of new strategies for the preparation of multicomponent supramolecular assemblies is a major challenge on the road to complex functional molecular systems. Here we present the use of a non‐porous self‐assembled monolayer from uC ₃₃‐NDI‐uC ₃₃ , a naphthalenediimide symmetrically functionalized with unsaturated 33 carbon‐atom‐chains, to prepare bicomponent supramolecular surface systems with a series of alkoxy‐pyrene ( PyrOR) derivatives at the liquid/HOPG interface. While previous attempts at directly depositing many of these PyrOR units at the liquid/HOPG interface failed, the multicomponent approach through the uC ₃₃‐NDI‐uC ₃₃ template enabled control over molecular interactions and facilitated adsorption. The PyrOR deposition restructured the initial uC ₃₃‐NDI‐uC ₃₃ monolayer, causing an expansion in two dimensions to accommodate the guests. As far as we know, this represents the first example of a non‐porous or non‐metal complex‐bearing monolayer that allows the stepwise formation of multicomponent supramolecular architectures on surfaces.

Abstract

Supramolecular surface systems: A non‐porous monolayer of a long‐carbon chain naphthalenediimide serves as template for the stepwise adsorption of a series of alkoxy‐pyrene derivatives at the liquid/HOPG interface. Depositing the guests onto the template causes a severe reorganization of the initial monolayer, as visualized by scanning tunneling microscopy.