Macromolecular Architectures of Corannulene: Synthesis, Properties, and Applications of Polymers Containing a Molecular Bowl of Carbon

Abstract

Corannulene (C20H10) is a bowl-shaped polycyclic aromatic hydrocarbon. The molecular curvature endows corannulene with a dipole moment, affinity for electrons, and the capacity to host fullerenes. Corannulene can also act as a guest in the cavity of gamma cyclodextrin. Corannulene is thus an appealing building block for polymer synthesis. It is envisaged that the multifaceted properties of corannulene can be combined with the modularity of synthetic polymers to access functional soft materials. Indeed, these efforts are now a decade old and some corannulene polymers have already been tested in real-life devices. In this perspective, we will contemplate the motivation behind these efforts, progress made within the past decade, and future prospects of the field.

Recent advances in supramolecular fullerene chemistry

“…345 The binding was found to be on the order of 10 3 M À1 (toluene) and a host-guest ratio of up to 3 : 1 was confirmed by NMR spectroscopy and ITC titrations. Apart from corannulene derivatives, [359][360][361] Nabeshima and colleagues developed a series of chiral concave p-systems comprising phosphorus atoms, 343,347 which bind C 60 due to the concaveconvex interactions. In addition to buckybowls, [362][363][364][365] a bowlshaped nanobelt reported by Wu and coworkers, which could selectively capture C 70 with a large binding constant (log(K a ) E 5; in toluene) from a mixture of C 60 /C 70 due to size and shape complementarity.…”

Thiol-epoxy ‘click’ chemistry: a focus on molecular attributes in the context of polymer chemistry

“…18,19 Corannulene is a molecular bowl of carbon that can be envisaged as the cap-region of fullerene C 60 . [20][21][22][23][24] This molecule is a curved and rigid polycyclic aromatic hydrocarbon. Its rigidity and bulk near the polymer backbone presents synthetic challenges especially at a homopolymer level.…”

Enhancing NIR Electrochromism with Twisted Copolymer Films of Corannulene-Carbazole and 3,4-Ethylenedioxythiophene

“…Corannulene, a nonplanar π molecule, comprises five fused aromatic rings. Researchers who are interested in its unique bowl-shaped structure and electron density distribution have studied corannulene-based functional materials − in optoelectronics, − solar cells, , photodynamic therapy, and energy storage. , Furthermore, corannulene is considered as a twisted surface, which is promising for creating space in polymer films. A previous report has investigated the preparation of polycorannulene film, indicating that polycorannulene was a wavy-graphene sheet with a large average distance between two polycorannulene layers .…”