Unlike typical polycyclic aromatic hydrocarbons, such as coronene, which are flat and planar, corannulene is a molecular bowl of carbon. It can be imagined as the cap region of fullerene C₆₀ or an end of a single-walled carbon nanotube. This structural distinction manifests itself in unique properties. For example, corannulene exhibits bowl-flipping dynamics, electron accepting capability, and formation of a ball-in-socket type of interaction with C₆₀. These varied properties allow for application of corannulene in a myriad of disciplines ranging from organic electronics and sensing to energy storage and self-assembly. In this feature article, our goal is to discuss the major synthetic developments in corannulene chemistry which allow the scientific community access to this beautiful molecule in a practical fashion, the unique properties of the corannulene nucleus that sets it apart from the planar polynuclear aromatic hydrocarbons, and lastly its applications in the arena of materials chemistry.

Single and multiple post-polymerization modifications of poly(glycidyl methacrylate) scaffold through the nucleophilic ring-opening reactions of the pendent epoxide groups are described.

In this study, we probe various aspects of a post-polymerization double-modification strategy involving sequential thiol–epoxy and esterification reactions for the preparation of dual-functional homopolymers. For this, a general reactive scaffold, poly(glycidyl methacrylate), carrying an aromatic end-group was prepared through an atom transfer radical polymerization (ATRP) process. The glycidyl side-chains of this polymer were subjected to a base-catalyzed ring opening reaction with the thiol nucleophiles. A systematic variation in the catalyst type, catalyst loading, reaction medium, reaction temperature, and reaction time suggested that the choice and amount of catalyst had a significant impact on the outcome of the thiol–epoxy reaction. End-group analysis by ¹H-NMR spectroscopy was employed to quantify the degree of the epoxy group conversion into the corresponding thio-ether moiety. The secondary hydroxyl groups generated as a result of the first functionalization reaction were then employed in the anchoring of a second functional group to the polymer repeat unit through an esterification reaction. Quantification studies suggested that an excess of the activated acid molecules was necessary to observe quantitative functional group transformation. Elemental analysis confirmed the chemical composition of the functionalized polymers. The obtained bi-functionalized polymers could be converted into a water soluble amphipathic structure in which each polymer repeat unit was substituted with a hydrophilic ammonium cation and a hydrophobic alkyl chain. Besides these, a carefully planned model compound study was also conducted to examine the regio-chemical aspects of the prepared polymers.