2D Supramolecular Structures of a Shape-Persistent Macrocycle and Co-deposition with Fullerene on HOPG

Abstract

Two 2D supramolecular structures of macrocycle 1 and 1/C60 have been obtained on HOPG by self-assembly under ambient conditions and investigated by high-resolution STM. The monolayers of 1 are characterized by structures with perfect ordering over relatively large areas. In the case of 1/C60, the size of the macrocycle 1 and the presence of two individual bithiophene units per ring lead in the final superstructure to a 1:2 stoichiometry. The fullerenes are not trapped at the graphite surface inside the macrocyclic holes but are located around the periphery of the bithiophene units. This clearly shows that the donor-acceptor interaction between C60 and the electron-rich units of the ring is the dominant factor for the structure formation.

Shape‐Switchable Azo‐Macrocycles

“…Shape persistent macrocycles comprising similar polyalkyl substituents have already been reported by Höger et al. [104][106][184] [196]- [198] Increased adsorption properties of these macrocycles with an increasing number of alkyl chains were observed. The driving force for the adsorption of the macrocycles at the surface is the nonspecific attractive van der Waals (vdW) interaction of the rigid and the flexible ring parts, including the alkyl chains, with the graphite surface.…”

Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules

“…42) was used to build supramolecular structures with C 60 [105]. Trichlorobenzene solutions of 1 or 1 plus fullerene were deposited in solution on HOPG.…”

All‐Carbon Scaffolds by Rational Design

“…[23] Today, molecular-resolution imaging by scanning tunneling microscopy (STM) enables the monitoring of the assembly of macrocyclic p-systems on surfaces. [32][33][34] Most importantly, the inspiration provided by the 2D networks 2 and 3 has led to a renaissance of annulene chemistry, half a century after the seminal work by Sondheimer and co-workers. [35][36][37][38][39][40] In fact, a variety of benzannellated dehydro [12]-and [18] annulene-derived substructures of graphyne [30,41] and graphdiyne [42][43][44] have been prepared, such as 4-9 ( Fig.…”