A Conjugated Figure‐of‐Eight Oligoparaphenylene Nanohoop with Adaptive Cavities Derived from Cyclooctatetrathiophene Core

Abstract

Af ully conjugated figure-of-eight nanohoop is presented with facile synthesis.T he moleculesl emniscular skeleton features the combination of two strained oligoparaphenylene loops and af lexible cyclooctatetrathiophenec ore.Its rigid yet guest-adaptive cavities enable the formation of the peanut-like 1:2h ost-guest complexes with C 60 or C 70 ,w hich have been confirmed by X-ray crystallography and characterizedi ns olution. Further computational studies suggest notable geometric variations and non-covalent interactions of the cavities upon binding with different fullerenes,a sw ell as overall conjugation comparable to cycloparaphenylenes.

Modular synthesis, host–guest complexation and solvation-controlled relaxation of nanohoops with donor–acceptor structures

“…Note that the single crystal of the complex was easier to achieve than the free-standing 6a, suggesting that C60 serves as a template for the crystal growth. 34 As shown in Figure 3a, a 1:1 host-guest complex formed with the C60 sited in the center of the nanohoop. The intermolecular distances of the host and the guest were in the range of 3.4-3.7 Å, indicating a dominant vdW interaction.…”

Successive Diels–Alder Cycloadditions of Cyclopentadiene to [10]CPP⊃C60: A Computational Study

“… 46 Same type of interactions are key in the synthesis of [10]cycloparaphenylene-fullerene [2]rotaxanes 47 and in the recently synthesized figure-of-eight nanohoop that forms peanut-like 1:2 host–guest complexes with C 60 or C 70 . 48 …”

“…46 Same type of interactions are key in the synthesis of [10]cycloparaphenylene-fullerene [2]rotaxanes 47 and in the recently synthesized figure-of-eight nanohoop that forms peanut-like 1:2 host−guest complexes with C 60 or C 70 . 48 Very recently, Ribas et al 49 reported the synthesis of a threeshell, matryoshka-like complex in which C 60 inside a [10]CPP is in turn encapsulated inside a self-assembled nanocapsule. Bingel cyclopropanation to this matryoshka-like complex leads to the selective formation of a particular fullerene bisadduct.…”

“…The first [10]­CPP macrocycle stabilizes the binding of the second by maximizing π–π, CH−π, and attractive London dispersion interactions . Same type of interactions are key in the synthesis of [10]­cycloparaphenylene-fullerene [2]­rotaxanes and in the recently synthesized figure-of-eight nanohoop that forms peanut-like 1:2 host–guest complexes with C 60 or C 70 …”

Composition‐selective full inclusion host–guest interaction of azobenzene‐containing photoresponsive nanoring with fullerene C60

“…Currently, the development of host‐guest systems involving fullerenes has attracted much attention for chemical sensor, 1,2 supramolecular and electric materials, 3,4 nanoscale mechanics 5,6 and separation of specific fullerenes 7 . Carbon nanorings (CNRs) 8–14 and ligand–metal ring are two most popular hosts for fullerenes 15,16 . It is known that the selective and efficient encapsulation for the fullerene guests is an essential property in design of stable host‐guest supramolecular systems.…”