C60 Hexakisadducts with an Octahedral Addition Pattern − A New Structure Motif in Organic Chemistry

Hirsch, Andreas; Vostrowsky, O.

doi:10.1002/1099-0690(200103)2001:5<829::aid-ejoc829>3.0.co;2-v

Cited by 153 publications

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“…In particular, hexakis-adducts of [60]fullerene with a Th-symmetrical octahedral addition pattern have a unique three-dimensional structure which allows the introduction of six one-type or mixed-types addends. 10,11 Such derivatives can be obtained in one synthetic step by the addition of malonates to C60, but it has been somehow limited by the low yields resulting with bigger malonates, as the reaction is very sensitive to steric effects. 12 We have recently developed a procedure based on a click-chemistry approach which provides hexakis-adducts with twelve alkyne or azide terminal groups in high yields from simple malonates.…”

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Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

et al. 2015

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Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

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“…Die daraus gewonnenen Erkenntnisse könnten sich als nütz-lich für die Entwicklung von Wirkstofftransportsystemen erweisen. Beispiele für solche dendritischen Amphiphile sind 1) das globuläre Amphifulleren 1, [1] das in einem oktaedrischen [1:5]-Additionsmuster [4] ein Paar von Carboxy-terminierten Amiddendronen und fünf Dodecylmalonataddenden an den Fullerenkern gebunden enthält, und 2) das Calixarenderivat 2,[3] das analoge hydrophile und lipophile Bauelemente aufweist.Im Amphiphil 1 ist der Platzbedarf der hydrophilen und hydrophoben Bereiche ausbalanciert, und es herrscht freie konformative Beweglichkeit, was eine Bandbreite energetisch günstiger Packungsmotive sowohl für micellare Strukturen als auch für ausgedehnte liposomale Doppelschichtstrukturen gewährleistet. Das tatsächliche Vorliegen unterschiedlicher Aggregationsformen wurde durch elektronenmikroskopische Untersuchungen bestätigt.…”

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Schaltbare supramolekulare Organisation strukturdefinierter Micellen basierend auf einem amphiphilen Fulleren

et al. 2005

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Wir untersuchen seit einiger Zeit die Synthese und supramolekulare Organisation von dendritischen Amphiphilen, die als Kernbausteine Fullerene oder Calixarene enthalten. [1][2][3] Dabei interessiert uns neben der Herstellung von strukturpersistenten Micellen besonders der Aufbau von funktionalisierbaren Micellen oder Liposomen, deren Aggregationsverhalten durch einen externen Stimulus gesteuert werden kann. Die daraus gewonnenen Erkenntnisse könnten sich als nütz-lich für die Entwicklung von Wirkstofftransportsystemen erweisen. Beispiele für solche dendritischen Amphiphile sind 1) das globuläre Amphifulleren 1, [1] das in einem oktaedrischen [1:5]-Additionsmuster [4] ein Paar von Carboxy-terminierten Amiddendronen und fünf Dodecylmalonataddenden an den Fullerenkern gebunden enthält, und 2) das Calixarenderivat 2,[3] das analoge hydrophile und lipophile Bauelemente aufweist.Im Amphiphil 1 ist der Platzbedarf der hydrophilen und hydrophoben Bereiche ausbalanciert, und es herrscht freie konformative Beweglichkeit, was eine Bandbreite energetisch günstiger Packungsmotive sowohl für micellare Strukturen als auch für ausgedehnte liposomale Doppelschichtstrukturen gewährleistet. Das tatsächliche Vorliegen unterschiedlicher Aggregationsformen wurde durch elektronenmikroskopische Untersuchungen bestätigt.[2a] Im Unterschied dazu haben wir das Amphiphil 2 so konstruiert, dass eine relativ starre T-förmige Struktur vorliegt, [3] die keine Packung zu sehr ausgedehnten Überstrukturen wie Liposomen gewährleistet. In der Tat haben wir zeigen können, dass bei der supramolekularen Organisation von 2 ausschließlich sehr kleine, stark gekrümmte Aggregate entstehen, die das erste

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“…Therefore, estimation of the average number of the amine molecules added to fullerenes is always troublesome [2]. We took this into account when choosing the experimental methods in this study.Importantly, studies of the regioselectivity of the addition to C 60 [13] showed that energetically allowed are reactions between the reagent and the most reactive carbon atoms (C3C bonds between two hexa- …”

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“…Importantly, studies of the regioselectivity of the addition to C 60 [13] showed that energetically allowed are reactions between the reagent and the most reactive carbon atoms (C3C bonds between two hexa-…”

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confidence: 99%

Synthesis and Polar and Electrooptical Properties of a Butylamine Derivative of Fullerene C60

et al. 2005

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A butylamine derivative of fullerene was prepared by the reaction of butylamine with fullerene C 60 .The experimental electrooptical and dipole characteristics of the derivative were compared with the corresponding calculated PM3 data. The reaction product proved to be inhomogeneous in the number of the amine molecules added; it contains polar multiadducts of C 60 with noncentrosymmetric distribution of covalently bound amino groups over the fullerene core.The molecular characteristics and synthesis methods for fullerene derivatives attract much attention of materials scientists, as usually only chemical modification allows practical application of the unique properties of the framework forms of molecular carbon [1]. By contrast to fullerenes C 60 and C 70 , their amino derivatives are well soluble in organic solvents [2] and surpass unmodified fullerenes in photophysical properties [3]. A large potential of fullerenecontaining materials and easy preparation of fullerene compounds with amines stimulated in recent years synthesis of various amine derivatives of C 60 and C 70 [235], including water-soluble derivatives suitable for studying the biological activity [6]. It was noted that ÄÄÄÄÄÄÄÄÄÄÄÄ the reaction products of fullerenes with amines include regioisomers with different numbers of amine molecules added [2, 7310] and also that the composition and properties of amine derivatives of fullerenes are strongly dependent on the synthesis conditions [7].The mechanism of covalent addition of primary amines to fullerenes C 60 and C 70 was studied by various spectral methods [2,4, 8310]. These studies showed that the reactions go in two steps, namely, oneelectron transfer from the electron donor (amine) to electron acceptor (fullerene), yielding a radical anion C 60 ! . (C 70 ! . ) and a radical cation RNH 2 +. , which further recombine in the second step by the following scheme:In this study, the reaction product (A3C 60 ) of butylamine (A) with fullerene C 60 (C 60 ) was examined by the methods of dielectric polarization of molecules [11] and electrooptical Kerr effect [12] in toluene.As already mentioned, reactions of primary amines with fullerenes, depending on the conditions, yield virtually inseparable multiadducts with difficult-tocontrol number of the amine molecules added. Therefore, estimation of the average number of the amine molecules added to fullerenes is always troublesome [2]. We took this into account when choosing the experimental methods in this study.Importantly, studies of the regioselectivity of the addition to C 60 [13] showed that energetically allowed are reactions between the reagent and the most reactive carbon atoms (C3C bonds between two hexa-

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C60 Hexakisadducts with an Octahedral Addition Pattern − A New Structure Motif in Organic Chemistry

Cited by 153 publications

References 49 publications

Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

Schaltbare supramolekulare Organisation strukturdefinierter Micellen basierend auf einem amphiphilen Fulleren

Synthesis and Polar and Electrooptical Properties of a Butylamine Derivative of Fullerene C60

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