Di‐ and Dodeca‐Mitsunobu Reactions on C<sub>60</sub> Derivatives: Post‐Functionalization of Fullerene Mono‐ and Hexakis‐Adducts

Pierrat, Philippe; Réthoré, Céline; Müller, Thierry; Bräse, Stefan

doi:10.1002/chem.200902141

Cited by 31 publications

(15 citation statements)

References 26 publications

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“…The CO loss infers epoxy group inside the molecule, which is a common phenomenon in mass spectrometry analysis of fullerene epoxide [4]. 1 HNMR analysis supports the existence of phenyl groups in the two molecules and hydroxyl group in C 60 Ph 9 OH (Fig. 4).…”

Section: Nmr Spectramentioning

confidence: 82%

“…Chemical modifications provide ways to solve these problems. Richly functionalized fullerenes not only furnish aesthetically appealing molecular entities, but also show even better promising applications than pure parents or mono-functionalized ones for improved biological compatibility and photoelectric properties [1][2][3]. There are many approaches for fullerene multiple modifications [4,5], among them it is an efficient way by using chlorofullerene C 60 Cl 6 as precursor to get useful fullerene derivatives [6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

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Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

et al. 2015

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fullerenes have better compatibility and application possibility than parent or mono-modificated C 60 . Friedel-Crafts reaction of chlorofullerene is a low-cost way to acquire useful multifunctional [60]fullerenes, yet products obtained by which bearing more than six function groups are rarely involved owing to their low yields. Herein chlorofullerene oligomer (CFO), a by-product during C 60 Cl 6 synthesis, was used for fullerene phenylation by a facile solvothermal method and the insoluble CFO was converted completely into highly phenylated fullerenes with good solubility in common organic solvents. Two phenylfullerenes among the product, C 60-Ph 9 OH and C 60 Ph 12 O 2 , were isolated for spectroscopic characterizations. The electrochemical properties of the two compounds were as well investigated for the first time which exhibit electroreductions with distinct negative potential shifts relative to C 60 . So the solvothermal approach provides convenient production of polyfunctional fullerenes and paves the way for their promising application investigation in material science.Electronic supplementary material The online version of this article (

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Section: Nmr Spectramentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

et al. 2015

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“…10, 13–18 Recently Sun and co‐workers developed an alternative method for the synthesis of T h ‐symmetrical hexakisadducts 19. 20 Using a significantly increased amount of CBr 4 , no DMA was necessary in the synthesis of a variety of hexakisadducts 21–26. So far only a few water‐soluble hexakisadducts involving an octahedral addition pattern have been reported.…”

Section: Introductionmentioning

confidence: 99%

“…[19,20] Using a significantly increased amount of CBr 4 , no DMA was necessary in the synthesis of a variety of hexakisadducts. [21][22][23][24][25][26] So far only a few water-soluble hexakisadducts involving an octahedral addition pattern have been reported. Examples are mixed [3:3]hexakisadducts containing ammonium or carboxylic acid termini [10,27,28] or amphiphilic [5:1]hexakisadducts leading to the formation of shape-persistent micelles.…”

Section: Introductionmentioning

confidence: 99%

Giant Fullerene Polyelectrolytes Composed of C₆₀ Building Blocks with an Octahedral Addition Pattern and Discovery of a New Cyclopropanation Reaction Involving Dibromomalonates

Hörmann

Hirsch

2013

Chemistry A European J

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We report here on the facile synthetic access of a new family of bis-, tetra-, hexa-, and heptafullerenes (prototypes I-IV), which can be easily converted into very water soluble polyelectrolytes with up to 60 charges located on their periphery. Their very regioselective formation is based on the use of C(2v)-symmetrical pentakisadducts 3 and hexakisadducts 2 as key intermediates. All fullerene moieties incorporated in these macromolecular structures involve a complete or partial octahedral addition pattern. Tripod-shaped tetrafullerenes 9a,b (type II), which can accumulate up to thirty positive or negative charges, are very soluble in acidic or basic water, respectively. Hexafullerenes 13a,b (type III) were synthesized via isoxazolinofullerenes 10 followed by photolytic cleavage of the isoxazoline group. The giant heptafullerene 1b (type IV) representing the anionic counterpart of the previously synthesized polyelectrolyte 1a can store up to 60 negative charges on its periphery within a defined three-dimensional structure. We also discovered a new cyclopropanation reaction of C(60) involving dibromomalonates and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). This reaction allows even for the highly regioselective formation of hexakisadducts with an octahedral addition pattern without requiring activation with reversibly binding addends such as 9,10-dimethylanthracene (DMA).

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“…Over the years, different methods for the functionalization of the fullerene core have appeared1516171819202122. Chiral fullerene adducts are either generated through an inherent chiral addition pattern, through chiral addends or a combination of both 10c .…”

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confidence: 99%

Soccer goes BOXing: Synthetic access to novel [6:0] hexakis[(bisoxazolinyl)methano]fullerenes

Seifermann

Réthoré

Müller

et al. 2013

Sci Rep

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The syntheses of [6:0] hexakis[(bisoxazolinyl)methano]fullerenes are presented. Two derivatives could be directly obtained using conditions developed by the Sun group. For the remaining products, a two stage protocol had to be developed. All compounds we obtained in synthetically useful scales and were purified via column chromatography with standard achiral phase. These new fullerene adducts bear six metal-chelation sites which are aligned in the three orthogonal space directions and are disposed on a completely rigid scaffold. First experiments indicate that the generation of six-fold metal-complexes is possible with these structures. This makes them very appealing as ligands in asymmetric catalysis and as building blocks in higher supra-molecular assemblies.

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Di‐ and Dodeca‐Mitsunobu Reactions on C₆₀ Derivatives: Post‐Functionalization of Fullerene Mono‐ and Hexakis‐Adducts

Cited by 31 publications

References 26 publications

Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

Giant Fullerene Polyelectrolytes Composed of C₆₀ Building Blocks with an Octahedral Addition Pattern and Discovery of a New Cyclopropanation Reaction Involving Dibromomalonates

Soccer goes BOXing: Synthetic access to novel [6:0] hexakis[(bisoxazolinyl)methano]fullerenes

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Di‐ and Dodeca‐Mitsunobu Reactions on C60 Derivatives: Post‐Functionalization of Fullerene Mono‐ and Hexakis‐Adducts

Cited by 31 publications

References 26 publications

Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

Convenient Fullerene Derivatization: A Solvothermal Method for the Acquisition of Polyarylated Fullerenes with Aryl Group Number Above Five

Giant Fullerene Polyelectrolytes Composed of C60 Building Blocks with an Octahedral Addition Pattern and Discovery of a New Cyclopropanation Reaction Involving Dibromomalonates

Soccer goes BOXing: Synthetic access to novel [6:0] hexakis[(bisoxazolinyl)methano]fullerenes

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Di‐ and Dodeca‐Mitsunobu Reactions on C₆₀ Derivatives: Post‐Functionalization of Fullerene Mono‐ and Hexakis‐Adducts

Giant Fullerene Polyelectrolytes Composed of C₆₀ Building Blocks with an Octahedral Addition Pattern and Discovery of a New Cyclopropanation Reaction Involving Dibromomalonates