Configurations of a Calix[8]arene and a C₆₀/Calix[8]arene Complex on a Au(111) Surface

Abstract

Calixarenes and fullerenes have novel properties that make them ideal materials for nanoscale electronic devices. [1][2][3][4] If fullerenes can be placed within a calixarene to form an ordered array, it could be possible to operate them and fabricate nanoscale circuits. As an essential prerequisite, the configurations of calixarenes and fullerenes included within calixarene units at a solid surface must be understood to construct the nanoscalar architecture. Calixarenes have a highly flexible molecular conformation, which is important in various chemical reactions and host-guest chemistry. [5,6] To understand the variety of molecular conformations that exist, resolution at the atomic or submolecular level is important, and is a challenging research activity in calixarene studies.Herein, we report the results of the construction and investigation of a calix[8]arene derivative, OBOCMC8 (C 104 H 128 O 24 ), [7] and the inclusion of C 60 in OBOCMC8 (C 60 / OBOCMC8). Scheme 1 a illustrates the chemical insertion of the buckyball into the calix structure, [8,9] and the structures of the calixarene and the inclusion complex are shown in Scheme 1 b and c, respectively. Well-ordered arrays of OBOCMC8 and C 60 /OBOCMC8 can be constructed on a Au(111) surface, and are clearly observed by scanning tunneling microscopy (STM). The results directly demonstrate a stable conformation of OBOCMC8 and the possibility of C 60 inclusion.The electrochemical behavior of the Au(111) surface in a solution containing OBOCMC8 and C 60 /OBOCMC8 was investigated by cyclic voltammetry. Cyclic voltammograms (CVs) were recorded in 0.1m HClO 4 using the so-called hanging meniscus method. After recording the standard CV of a bare Au(111) surface, a small amount of OBOCMC8 solution was added into the electrochemical cell. As a result, the oxidation peak, which is found at þ1.3 V for Au (111) [*] Prof.

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

“…44) supported on the Au(111) surface was investigated by electrochemical STM [109], leading to submolecular resolution of the self-assembly of calyxarenes molecules. Calyxarenes are suitable to fabricate nanoscale electronic devices because of their ability to host fullerene molecules.…”

“…The latter is an interesting approach to improve the electronic properties of organic films. Indeed, it has been recently demonstrated that the electron field-effect [109]. © (2003) Wiley mobility in C 60 films grown on a pentacene buffer layer is 4-5 times higher compared to when the buffer layer is absent [113].…”

Mesoscopic self-organization of a self-assembled supramolecular rectangle on highly oriented pyrolytic graphite and Au(111) surfaces

“…These processes will play a critical role in the so-called ''bottom-up'' strategy of nanofabrication. Therefore, understanding the organization of molecules on solid surfaces is important, both from a fundamental and applied perspective, for the construction of surface molecular nanostructures and nanodevices (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). A self-organized molecular pattern with control of structure and derived concomitant function could provide promising materials for the construction of nanodevices that cannot be prepared by conventional microfabrication.…”

Two-dimensional self-assemblies of telechelic organic compounds: structure and surface host–guest chemistry

“…The size and/or shape complement between the host cavity and the guest molecules is frequently proposed as a key factor responsible for the formation of the desired pattern assembly. Until now, various two-dimensional molecular templates as well as designed host-guest systems have been constructed on solid supports and studied at the molecular scale by means of scanning tunnelling microscopy (STM) [36][37][38][39]. Steered by two-dimensional molecular templates, the desired patterns of C 60 , porphyrin and phthalocyanine derivatives, and many other functional molecules, have been accomplished [26,38,39].…”

“…In recent years, surface host-guest chemistry has received great attention [14,26,[36][37][38][39]. Welldefined molecular networks with appropriate nanopatterns can serve as surface molecular templates to drive the selected molecular organization of guest molecules in a precisely controlled position, orientation and interdistance [36].…”