Onion‐Type Complexation Based on Carbon Nanorings and a Buckminsterfullerene

Kawase, Takeshi; Tanaka, Kenji; Shiono, Nami; Seirai, Yohko; Oda, Masaji

doi:10.1002/anie.200353517

Cited by 151 publications

(106 citation statements)

References 42 publications

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“…18,19 In the case of [6]CPPA, this molecule takes C 60 in the cavity to form [6]CPPA*C 60 . 20 [4]CC 2,8 having two hexyl groups at 6 and 12 positions strongly encapsulates C 60 with an extremely high binding constant (log K a = 11.5 in toluene), and C 60 rolls anisotropically in a bearing at the molecular scale. 3).…”

Section: Oligophenylene Macrocyclesmentioning

confidence: 99%

Multifunctional π-expanded oligothiophene macrocycles

2015

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This tutorial review summarizes recent progress in the design, synthesis, and multifunctional properties of fully conjugated macrocyclic π-systems. We focus on the π-expanded oligothiophene macrocycles after a short survey of macrocyclic conjugated loops and belts such as [n]cycloparaphenylenes, cyclic[n]para-phenylacetylenes, [4]cyclo-2,8-crysenylenes, and cyclo[n]thiophenes. Fully conjugated π-expanded oligothiophene macrocycles possess shape-persistent but sometimes pliable π-frames, and the electronic and optoelectronic properties of the macrocycles largely depend on the π-systems inserted into the oligothiophene macrocycles. Among them, the π-expanded oligothiophene macrocycle composed of 2,5-thienylenes, ethynylenes, and vinylenes is one of the most widely applicable macrocycles for constructing multifunctional π-systems. These π-expanded oligothiophene macrocycles from small to very large ring sizes can be prepared via a short step procedure, and their various solid state structures can be determined by X-ray analysis. Since these macrocycles have inner and outer domains, specific information concerning structural, electronic, and optical properties is expected. Furthermore, π-expanded oligothiophene macrocycles with alkyl substituents exhibit various morphologies depending on nanophase separation of molecules, and a morphological change is observed for the molecular switch.

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Section: Oligophenylene Macrocyclesmentioning

confidence: 99%

Multifunctional π-expanded oligothiophene macrocycles

2015

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“…The distributions of the frontier orbitals depend on the complex;t he HOMO and LUMO, as wella st he HOMOÀ1a nd LUMO + 1, are located in different CPPs in [11]CPP' [6]CPP,a nd interlayer orbital interactions are observed for the LUMO and LUMO + 1i n [12]CPP' [7]CPP and [13]CPP' [8]CPP.D espite the differences in the distributions of the frontier orbitals, significant modulations of the HOMO and LUMO orbitale nergies are observed in all cases (see the Supporting Information for details). The results are consistent with the presence of interlayer interactions observeda nd suggested in multiwalled CNTs, including double-walled CNTs.…”

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confidence: 99%

“…Kawase further reported aternary complex composed of C 60 and two cycloparaphenyleneacetylenes of different sizes (Figure 1a). [6] Sygula reported am olecular tweezer with two corannulene units that encapsulated C 60 ; [7] the structure of the complex can be regarded as am odel structure of the focal point of bucky onions.…”

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confidence: 99%

“…The size-selective interaction between CPPs was first examined by mixing [6]CPP,a saguest, with an equimolar mixture of [8] HNMR titration experiments,d emonstratingt he exergonicc omplex formation,w ith a DG value of À18 kJ mol À1 (Table 1). This value is significantly smaller than that (À110kJmol )o btained by DFT calculations at the wB97X-D/6-31G(d)l evel, but this difference is attributable to the effect of the solvent.…”

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Shortest Double‐Walled Carbon Nanotubes Composed of Cycloparaphenylenes

et al. 2017

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The host-guest chemistry of cycloparaphenylenes (CPPs) of different sizes is described.[n]CPPs (n = 5, 6, 7, 8, and 10) selectively interactw ith [n + 5]CPPs,f orming complexes [n + 5]CPP'[n]CPP,w hich are the shortestd ouble-walled armchair carbon nanotubes. The size selectivity is dictated by the difference in diameters of the CPPs (that is, 0.34-0.35 nm), which maximizes attractivev an derW aals interactions. Theoretical calculations suggest that the orbital energies of the CPPs become perturbedu pon complex formation, and orbital mixing between the two CPPs is predicted for large CPP pairs. The association constants in 1,1,2,2-[D 2 ]tetrachloroethane, estimated by 1

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“…Besides Aida's work on macrocyclic structures, several molecular tweezers featuring porphyrins as binding motifs have also been reported [52,53], spearheaded by the work by Boyd and Reed on their "jaws" receptors [54][55][56]. More recently, concave recognition motifs [57,58], complementary to the convex surface of the fullerenes, like corannulene [59][60][61], or cyclophenyleneacetylenes, have been explored [62][63][64][65].…”

Section: Historical Notes On the Noncovalent Chemistry Of Fullerenesmentioning

confidence: 95%

Energy, supramolecular chemistry, fullerenes, and the sky

Pérez

2010

Pure and Applied Chemistry

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The search for cleaner and more abundant sources of energy is one of the major scientific challenges of the 21 st century. Owing to its privileged position as the central science, chemistry is bound to play a leading role in this quest. Within the search for new materials for organic photovoltaics, some of the work we have carried out concerning the supramolecular chemistry of electron donor and acceptor molecules is presented.

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Onion‐Type Complexation Based on Carbon Nanorings and a Buckminsterfullerene

Cited by 151 publications

References 42 publications

Multifunctional π-expanded oligothiophene macrocycles

Multifunctional π-expanded oligothiophene macrocycles

Shortest Double‐Walled Carbon Nanotubes Composed of Cycloparaphenylenes

Energy, supramolecular chemistry, fullerenes, and the sky

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