Corannulene Chalcogenides

Abstract

The introduction of chalcogen atoms into a polycyclic aromatic hydrocarbon structure is an established method to tune material properties. In the context of corannulene (C20H10), a fragment of fullerene C60, such structural adjustments have given rise to an emerging class of functional and responsive molecular materials. In this minireview, our aim is to discuss the synthesis and properties of such chalcogen (sulfur, selenium, and tellurium) derivatives of corannulene.

Self-Resetting Bistable Redox Molecular Machines for Fullerene Recognition

“… 10 , 11 The variety of protocols to include the S–S motif, either chemically or electrochemically, in synthetic compounds is widespread 12 , 13 and has been successfully applied in a variety of outstanding concepts. 14 , 15 Corannulene chalcogenides, 16 especially those bearing sulfur as the distinctive heteroatom, have been extensively studied due to their special electronic features when compared to the parent buckybowl, leading to materials with distinctive properties. 17 − 20 One of the most interesting characteristics is their electron donation ability to form stable adducts with fullerenes.…”

“…The model we propose herein, again driven by nature’s inspirational influence, is based on the formation and cleavage of disulfide (S–S) bridges . It is well-known that this motif is present in a vast assortment of biomolecules, especially in proteins, whose function is to provide stability to the molecule favoring the maturation (correct folding) progress toward their native state. , The variety of protocols to include the S–S motif, either chemically or electrochemically, in synthetic compounds is widespread , and has been successfully applied in a variety of outstanding concepts. , Corannulene chalcogenides, especially those bearing sulfur as the distinctive heteroatom, have been extensively studied due to their special electronic features when compared to the parent buckybowl, leading to materials with distinctive properties. − One of the most interesting characteristics is their electron donation ability to form stable adducts with fullerenes. − …”

Five‐fold‐symmetric Pentabromo‐ and Pentaiodo‐corannulenes: Useful Precursors of Heteroatom‐substituted Corannulenes

“…Another milestone was reported in 2012, featuring pentakis(pinacolatoboryl)corannulene 2 [7h] by regioselective iridium‐catalyzed borylation reaction. Various kinds of sym ‐penta‐substituted corannulene derivatives can be prepared from these materials, [7] including pentaaryl‐, [7b,i] pentaalkynyl‐, [7b,d,e] pentaoxy‐, [7b] pentafluoro‐, [7l] pentathio‐, [7a–c,j,k,n] pentaselenyl‐corannulenes [7m,n] . Yet, other kinds of quintuply substituted corannulenes such as pentaphosphinyl‐, pentaphosphoryl‐, and pentaamino‐corannulenes have not been explored.…”

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

“…Corannulene can be imagined as the smallest curved fragment of fullerene C 60 . − Interestingly, however, Barth and Lawton synthesized it nearly two decades before the discovery of C 60 . At the time of the first synthesis, it was unclear whether corannulene would adopt a planar or a nonplanar geometry.…”