Single and multiple post-polymerization modifications of poly(glycidyl methacrylate) scaffold through the nucleophilic ring-opening reactions of the pendent epoxide groups are described.
Corannulene (C 20 H 10) is a polycyclic hydrocarbon in which five six-membered rings surround a central five-membered ring to construct a bowl-like aromatic structure. Here we examine the development of synthetic strategies that allow for the growth of the peripheral aromatic rings as a means to extend the aromatic area of the central corannulene nucleus and provide access to unique nanocarbon molecules. s p 2-hybridised structures of carbon have fascinated the research community for a very long time. In 1985, buckminsterfullerene, otherwise known as C 60 , was discovered (Fig. 1a) 1. In this ball-shaped molecule, the curvature in the structure stems from the presence of fivemembered rings. In 1991, carbon nanotubes arrived on the scene 2. Here, the structure is cylindrical and composed of only rolled-up six-membered rings. In 2004, a sheet-like single layer from graphite-graphene-was isolated 3. All of these materials were shown to have extraordinary electronic and mechanical properties due to their unique curved or planar sp 2-hybridised aromatic structures. Inspired by these discoveries, chemists have been developing strategies to access such aromatic hydrocarbons through rational ('bottom-up') synthetic approaches. Scott's 12-step chemical synthesis of fullerene C 60 from a rationally designed precursor is a testament to the ingenuity and resourcefulness of organic chemists 4. In planar structures, nanographenes (well-defined cutouts of graphene with nano-scale dimensions) can now be prepared on a regular basis with a very diverse portfolio 5. It is expected that combining the planar structure of graphene with the curvature of fullerenes may produce hybrid materials with interesting properties 6-8. To induce non-planarity into nanographenes, a practical approach would be to introduce a fivemembered ring such as in the case of fullerene, C 60. A perfect building block that allows for such a structural arrangement to happen is corannulene (1)-a molecule in which five six-membered rings surround a central five-membered ring to give a bowl-like structure (Fig. 1b) 9-20. Corannulene also offers many beneficial features as a molecular building block. It has high solubility in common organic solvents. It can be derivatized in a well-defined manner. Due to synthetic ease, the derivatives can be prepared on a multigram scale. These attributes are important as they allow for the scalable preparation of carefully designed corannulene-based building blocks and the subsequent synthesis, purification and structural analysis of the larger (fused) aromatic systems. Recently, therefore, there has been a surge in employment of corannulene as a core molecule in the synthesis of extended aromatic structures. Our aim in this review article is to discuss
have been a fantastic support group for the occasionally much needed comic relief in the lab as well as sounding boards when it came to my queries. Additionally, group members from Asst Prof Felipe Garcia's research group namely Sim Ying, Davin and Asst Prof Garcia himself, thank you for the time and effort you have offered my way to teach me a branch of chemistry that was so foreign to me. I would also like to extend my gratitude to Ms Seow Ai Hua, Ms Charlene Poo, Ms Goh Ee Ling and Dr Li Yongxin for their help with the equipment and facilities I have utilised during my research.
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