Fullerene Wires Assembled Inside Carbon Nanohoops

Abstract

Carbon-nanohoop structures featuring one or more roundshaped cavities represent ideal supramolecular hosts for spherical fullerenes, with potential to form host-guest complexes that perform as organic semiconductors in the solid state. Due to the tight complexation between the shapecomplementary hosts and guests, carbon nanohoops have the potential to shield fullerenes from water and oxygen, known to perturb the electron-transport process. Many nanohoop receptors have been found to form host-guest complexes with fullerenes. However, there is only a little or no control over the long-range order of encapsulated fullerenes in the solid state. Consequently, the potential of these complexes to perform as organic semiconductors is rarely evaluated. Herein, we present a survey of all known nanohoop-fullerene complexes, for which the solid-state structures were obtained. We discuss and propose instances where the inclusion fullerene guests form discrete supramolecular wires, which might open up possibilities for their use in electronic devices.

Redox-switchable host–guest complexes of metallocenes and [8]cycloparaphenylene

“…15 Furthermore, host-guest complexes are often employed to template the synthesis of molecules with topological and mechanical entanglements, known as mechanical bonds, 16 which have played an essential role in the design and synthesis of artificial molecular machines. 17,18 Cycloparaphenylenes (CPPs) are fully π-conjugated macrocyclic hydrocarbon semiconductors that have emerged in recent years as promising nanomaterials for optoelectronic [19][20][21][22] and supramolecular [23][24][25] applications. First synthesized by Jasti 26 in 2008, nCPPs are now prepared on multigram scales and carried ( [5]CPP- [12]CPP) by commercial suppliers.…”

“…First synthesized by Jasti 26 in 2008, nCPPs are now prepared on multigram scales and carried ( [5]CPP- [12]CPP) by commercial suppliers. 27 In addition to binding many fullerenes via π-π interactions, 25 [n]CPPs and other carbon nanorings can be driven to form CH-π stabilized host-guest complexes, including a macrocyclic oligoanthracene-fullerene complex, 28 nested [n]CPPs, 29,30 pyri-dinium⊂dimethoxy- [8]CPP, 31 corannulene⊂ [4]cyclochrysenylene, 32 diquat⊂ [9]CPP, 33 triquinoline⊂ [12]CPP, 34 and a variety of polycyclic aromatic hydrocarbon (PAH)-[n]CPP complexes. 35 CH-π bonding is common in molecular crystals 36 and protein folding, 37 but not often the main interaction stabilizing a hostguest complex.…”

“…Cycloparaphenylenes (CPPs) are fully π-conjugated macrocyclic hydrocarbon semiconductors that have emerged in recent years as promising nanomaterials for optoelectronic 19–22 and supramolecular 23–25 applications. First synthesized by Jasti 26 in 2008, n CPPs are now prepared on multigram scales and carried ([5]CPP–[12]CPP) by commercial suppliers.…”

Fullerene-containing pillar[n]arene hybrid composites

“…[104][105][106] Research on other diverse cyclophanes with fullerene as the guest should particularly be paid attention to. [107][108][109][110][111][112][113]…”

Tuning Solid‐State Emission Behavior of Janus‐Type Anthracenes by Addition of Shielding Bridges

“…Not only does the spacer assist π‐π interactions with the Si⋅⋅⋅π interaction, [14] but it also fixes the conformation of the bridges as a clip shape to afford recognition. Suitable intermolecular fitting of the structures is essential for stabilizing the supramolecules of hydrocarbons [15] and crystals of multiply arylated compounds [16] by integrating weak dispersion interactions. The clips may embrace another clip and the anthracene ring so that three competitive interactions are expected in the condensed phase (Figure 1): clip‐clip, clip‐anthracene (ant), and ant‐ant.…”