Reaction of fullerene with benzocyclobutene homologs

Tago, Tetsuya; Minowa, Toshiyuki; Okada, Yukihiro; Nishimura, Jun

doi:10.1016/s0040-4039(00)61359-x

Cited by 51 publications

(25 citation statements)

References 15 publications

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“…1) at room temperature, apparently indicating that the flipping motion around these rings is highly restricted by the tether. 27,28 In Figure 1 we can also observe that in bisadducts 9 and 10 one of the methylene protons of cyclohexene rings is shifted to a considerably high field (doublets at d 3.44 and 3.26 ppm, respectively) which is in agreement with a structure of e isomers. 20 …”

Section: Lysine Derivativessupporting

confidence: 68%

Synthesis of [60]fullerene-based α-amino acid derivatives

Enes¹,

Tomé²,

Cavaleiro³

2005

Tetrahedron

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Section: Lysine Derivativessupporting

confidence: 68%

Synthesis of [60]fullerene-based α-amino acid derivatives

Enes¹,

Tomé²,

Cavaleiro³

2005

Tetrahedron

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“…We have examined several dihydrocyclobutaarenes 1 as a precursor of o ‐quinodimethane species and found that they underwent thermally allowed conrotatory electrocyclic ring opening and gave stable adducts such as 2 [Eq. (1)] 6,7. In these adducts, the aromatic rings are connected with [60]fullerene through a cyclohexene ring and located close to the fullerene surface so that some electronic interaction can arise.…”

Section: Functionalization Of Fullerenesmentioning

confidence: 99%

“…As described above, several o ‐quinodimethane adducts 2 having various aromatic rings (naphthalene, phenanthrene, pyrene, and so forth) were synthesized 6,7. Cyclic voltammetry (CV) of each adduct showed three reversible reduction waves, whose potentials were almost equal among the adducts and more negative than that of [60]fullerene itself 7.…”

Section: Properties Of Fullerene Adductsmentioning

confidence: 99%

“…Since 1992, we have been interested in the exohedral functionalization of [60]fullerene by using covalent bondings, mainly by o ‐quinodimethanes and related species, and in the properties of the resulting adducts,6–10 because of the availability of their precursors and the high stability of the adducts 11–13. In the course of our study, we have been especially engaged in the chemistry of bisadducts and their applications 14.…”

Section: Introductionmentioning

confidence: 99%

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Exohedral functionalization of fullerenes and supramolecular chemistry

Nakamura

Kato

2011

The Chemical Record

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We have investigated the exohedral functionalization of [60]fullerene, especially bisaddition; we have revealed the regioselectivity of bisaddition and the properties of obtained bisadducts. The bisaddition without any restriction generally shows low regioselectivity. The electronic and photophysical properties of bisadducts mainly depend on the addition patterns and are almost independent of the nature of addends. We have also attained the regioselective synthesis of bisadducts by controlling the distance and orientation between two reactive species with suitable covalent templates and their application into some functional materials. The synthesis of fullerene-containing interlocked molecules, such as catenanes and rotaxanes, was accomplished by using a noncovalent interaction, mainly a donor-acceptor interaction, in addition to the covalent functionalization. The bistable rotaxanes, which can serve as a molecular shuttle or switch, were also successfully prepared.

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“…C6o was easily converted to its derivatives by treatment with benzocyclobutene homologs using the thermally allowed conrotatory [tr 2 +~2] electrocyclic ring opening of the benzocyclobutene homologs (figure 63) (Tago et al 1993). Reaction of C6o with benzocyclobutenol 242 and its methoxy ether gave 1,9-dihydrofullerene cycloadduct 243 in high yields (figure 64).…”

Section: An Overview Of Fullerene Chemistrymentioning

confidence: 99%