Solid state photochemistry for fullerene functionalization: Solid state photoinduced electron transfer in the Diels-Alder reaction with anthracenes

Mikami, Kōichi; Matsumoto, Shoji; Tonoi, Takayuki; Okubo, Yasutaka; Suenobu, Tomoyoshi; Fukuzumi, Shunichi

doi:10.1016/s0040-4039(98)00572-3

Cited by 43 publications

(20 citation statements)

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“…[19,22] So far, a solid-state reaction using a ªvibrating millº (vm)-technique gave the best yield of 3 (55 %). [22c] Solid-state reactions were also explored in order to prepare the two related monoadducts 6 [24] and 7, [22c] either with the vm-technique (7, 62%) [22c] or by photochemistry (6, 30 %). [24] We report here on the efficient preparation of seven monoadducts of anthracenes and [60]fullerene (1, C 60 ) by addition reactions of the dienophilic electrophile 1 and seven anthracenes in solution and at ambient or lower temperature.…”

Section: Resultsmentioning

confidence: 99%

“…[22c] Solid-state reactions were also explored in order to prepare the two related monoadducts 6 [24] and 7, [22c] either with the vm-technique (7, 62%) [22c] or by photochemistry (6, 30 %). [24] We report here on the efficient preparation of seven monoadducts of anthracenes and [60]fullerene (1, C 60 ) by addition reactions of the dienophilic electrophile 1 and seven anthracenes in solution and at ambient or lower temperature. Particularly high yields were obtained in several cases by direct crystallization (precipitation) of the monoadducts from the reaction mixtures, thereby inhibiting further addition reactions and thermolytic decomposition (see Table 1 and Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

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Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

2001

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The efficient preparation of monoadducts of [60]fullerene and seven anthracenes (anthracene, 1-methylanthracene, 2-methylanthracene, 9-methylanthracene, 9,10-dimethylanthracene, 2,3,6,7-tetramethylanthracene, and 2,6-di-tert-butylanthracene) by cycloaddition in solution is described. The seven mono-adducts of [60]fullerene and the anthracenes were characterized spectroscopically and were obtained in good yields as crystalline solids. The monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 2-methylanthracene and 9,10-dimethylanthracene crystallized directly from the reaction mixture. The thermolytic decomposition at 180 degrees C of the crystalline monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 9-methylanthracene and 9,10-dimethylanthracene all gave rise to the specific formation of a roughly 1:1 mixture of [60]fullerene and the corresponding antipodal bisadducts ("trans-1"-bisadducts) of [60]fullerene and the anthracenes. In contrast, the crystalline monoadducts of [60]fullerene and the anthracene derivatives 2-methylanthracene, 2,3,6,7-tetramethylanthracene and 2,6-di-tert-butylanthracene all decomposed to [60]fullerene and anthracenes (without detectable formation of bisadducts) upon heating in the solid state to temperatures of 180 to 240 degrees C. The formation of the antipodal bisadducts from thermolytic decomposition of crystalline samples of the monoadducts was rationalized by topochemical control.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

2001

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“…151 A well-ground mixture of the reactants was irradiated, producing 30% of the mono-adduct 83 (Fig. 5) and 19% of a bis-adduct, the exact isomer of which was not identified.…”

Section: Additions To 9-substituted Anthracenementioning

confidence: 99%

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

2003

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“…This offers the possibility of stabilizing electron donor molecules. This property can be exploited in a donor-acceptor system where fullerenes promote charge separation and reduce the recombination, as for example photovoltaics [415], photochemistry [416], photobiology [417], [418], and medicine [419]. Referring to this last sector, nanomedicine is based on the development of new nanosized multifunctional platforms [420].…”

Section: Fullerenesmentioning

confidence: 99%

Functionalization of Carbon Nanomaterials for Biomedical Applications

Liu

Speranza

2019

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Over the past decade, carbon nanostructures (CNSs) have been widely used in a variety of biomedical applications. Examples are the use of CNSs for drug and protein delivery or in tools to locally dispense nucleic acids to fight tumor affections. CNSs were successfully utilized in diagnostics and in noninvasive and highly sensitive imaging devices thanks to their optical properties in the near infrared region. However, biomedical applications require a complete biocompatibility to avoid adverse reactions of the immune system and CNSs potentials for biodegradability. Water is one of the main constituents of the living matter. Unfortunately, one of the disadvantages of CNSs is their poor solubility. Surface functionalization of CNSs is commonly utilized as an efficient solution to both tune the surface wettability of CNSs and impart biocompatible properties. Grafting functional groups onto the CNSs surface consists in bonding the desired chemical species on the carbon nanoparticles via wet or dry processes leading to the formation of a stable interaction. This latter may be of different nature as the van Der Waals, the electrostatic or the covalent, the π-π interaction, the hydrogen bond etc. depending on the process and on the functional molecule at play. Grafting is utilized for multiple purposes including bonding mimetic agents such as polyethylene glycol, drug/protein adsorption, attaching nanostructures to increase the CNSs opacity to selected wavelengths or provide magnetic properties. This makes the CNSs a very versatile tool for a broad selection of applications as medicinal biochips, new high-performance platforms for magnetic resonance (MR), photothermal therapy, molecular imaging, tissue engineering, and neuroscience. The scope of this work is to highlight up-to-date using of the functionalized carbon materials such as graphene, carbon fibers, carbon nanotubes, fullerene and nanodiamonds in biomedical applications.

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Solid state photochemistry for fullerene functionalization: Solid state photoinduced electron transfer in the Diels-Alder reaction with anthracenes

Cited by 43 publications

References 20 publications

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes

Functionalization of Carbon Nanomaterials for Biomedical Applications

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