Synthesis and structural evaluation of closed-shell folded and open-shell twisted hexabenzo[5.6.7]quinarene

By alexandreCommunication

Synthesis and structural evaluation of closed-shell folded and open-shell twisted hexabenzo[5.6.7]quinarene

In recent years, research in the field of organic synthesis has led to the development of a wide range of novel molecules with unique and interesting properties. One such class of molecules is hexabenzo[5.6.7]quinarene, which has attracted attention due to its ability to adopt both closed-shell folded and open-shell twisted conformations. These two forms of hexabenzo[5.6.7]quinarene have distinct properties and are of interest for a variety of applications including molecular electronics and catalysis. This article will discuss the synthesis and structural evaluation of both closed-shell folded and open-shell twisted hexabenzo[5.6.7]quinarene.

Synthesis of Closed-Shell Folded Hexabenzo[5.6.7]quinarene

The closed-shell folded conformation of hexabenzo[5.6.7]quinarene can be synthesized through a multi-step process. The first step involves the preparation of the hexaarylbenzene intermediate, which can be achieved through the reaction of six equivalents of aryl magnesium bromide with one equivalent of benzophenone. This is followed by cyclization of the intermediate in the presence of a strong acid catalyst, which results in the formation of the closed-shell folded hexabenzo[5.6.7]quinarene.

The closed-shell folded conformation of hexabenzo[5.6.7]quinarene has a compact structure with a diameter of approximately 1 nm. This conformation has been found to exhibit interesting mechanical properties and may have potential applications in the development of nanoscale devices.

Scanning tunneling microscopy studies have revealed that the closed-shell folded conformation of hexabenzo[5.6.7]quinarene exhibits a highly ordered arrangement on a surface, indicating potential applications in surface functionalization and patterning.

Synthesis of Open-Shell Twisted Hexabenzo[5.6.7]quinarene

The open-shell twisted conformation of hexabenzo[5.6.7]quinarene can be synthesized through a similar multi-step process as the closed-shell folded conformation. However, the final cyclization step is typically carried out at a lower temperature and for a shorter duration, which promotes the formation of the twisted conformation.

The open-shell twisted conformation of hexabenzo[5.6.7]quinarene has a unique structure with alternating single and double bonds, resulting in a more planar and extended molecule compared to the closed-shell folded conformation. This conformation has been found to exhibit interesting electronic properties and may have potential applications in organic electronics.

X-ray crystallography studies of the open-shell twisted conformation of hexabenzo[5.6.7]quinarene have revealed a highly twisted and contorted structure, which may be responsible for its unique electronic properties.

Structural Analysis Techniques

The structural evaluation of hexabenzo[5.6.7]quinarene can be carried out using a variety of techniques including X-ray crystallography, NMR spectroscopy, and scanning tunneling microscopy.

X-ray crystallography is a powerful technique that allows for the determination of the 3D structure of molecules at high resolution. This technique has been used to determine the structures of both the closed-shell folded and open-shell twisted conformations of hexabenzo[5.6.7]quinarene.

NMR spectroscopy is another useful technique that provides information on the bonding and electronic properties of molecules. This technique has been used extensively to study the electronic properties of hexabenzo[5.6.7]quinarene in its open-shell twisted conformation.

Scanning tunneling microscopy is a surface-sensitive technique that allows for the imaging of molecules on surfaces with atomic resolution. This technique has been used to study the arrangement of hexabenzo[5.6.7]quinarene in its closed-shell folded conformation on surfaces.

Applications of Hexabenzo[5.6.7]quinarene

The unique structural and electronic properties of hexabenzo[5.6.7]quinarene make it of interest for a variety of applications including molecular electronics, catalysis, and surface functionalization.

In molecular electronics, hexabenzo[5.6.7]quinarene has been investigated as a potential candidate for use in field-effect transistors and memory devices due to its interesting electronic properties.

In catalysis, hexabenzo[5.6.7]quinarene has been found to exhibit interesting activity as a catalyst for various organic reactions including the reduction of nitroarenes and the oxidation of alcohols.

In surface functionalization, the highly ordered arrangement of hexabenzo[5.6.7]quinarene in its closed-shell folded conformation may have potential applications in the development of surface patterning techniques.

The synthesis and structural evaluation of both closed-shell folded and open-shell twisted hexabenzo[5.6.7]quinarene have been discussed in this article. These two conformations of hexabenzo[5.6.7]quinarene exhibit distinct structural and electronic properties, which make them of interest for a variety of applications including molecular electronics, catalysis, and surface functionalization.

Further research is needed to fully understand the properties of hexabenzo[5.6.7]quinarene and its potential applications. However, its unique structural and electronic properties make it a promising candidate for the development of novel materials in the field of organic chemistry.