Chemical Modification of Endohedral Metallofullerene La@C<sub>82</sub> with 3-chloro-3-phenyldiazirine

Ishitsuka, Midori O.; Enoki, Haruka; Tsuchiya, Takahiro; Slanina, Zdenêk; Mizorogi, Naomi; Nagase, Shigeru; Liu, Michael T. H.; Akasaka, Takeshi

doi:10.1080/10426501003773464

Cited by 8 publications

(4 citation statements)

References 20 publications

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“…In other words, the encaged metal atom has a directional effect controlling the reactivity of the cage Chlorophenyldiazirine 148 was applied for the functionalization of La@C 2v (9)-C 82 . 362 EPR spectrum of the purified product suggested the existence of two inseparable isomers in a ratio of 57:43. By analogy with Ad: addition to La@C 2v (9)-C 82 , the site of addition was proposed to be the same position (C(1)−C(2) site) with 270a−274a.…”

Section: Endohedral Metallofullerenesmentioning

confidence: 97%

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Carbene Additions to Fullerenes

2013

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CONTENTS 1. Introduction 7209 2. Carbene Addition to Empty Fullerenes 7210 2.1. Dihalocarbenes 7210 2.1.1. Dihalocarbene Additions to C 60 7210 2.1.2. Dihalocarbene Additions to C 70 7212 2.1.3. Dihalocarbene Additions to Fullerene Fragments 7213 2.2. Decomposition of Diazo Compounds 7215 2.2.1. Thermolysis of Diazo Compounds 7215 2.2.2. Photolysis of Diazo Compounds 7223 2.2.3. In-Situ Generation of Diazo Compounds 7223 2.2.4. Isomerization of Fulleroids to Methanofullerenes 7228 2.3. Decomposition of Diazirines 7233 2.3.1. Chemical Probe 7233 2.3.2. Photoaffinity Labeling 7237 2.3.3. Fullerene Sugars 7237 2.3.4. Addition−Elimination Reaction 7238 2.4. Decomposition of Diazonium Salts 7238 2.5. Alkoxycarbenes 7238 2.6. Vinylcarbenes 7239 2.7. Basic Treatment of Malonates in the Presence of Iodine 7240 2.8. Photolysis of Benzocyclobutenediones 7240 2.9. α-Ketocarbenes 7240 2.10. Fischer Carbene Complexes 7241 2.11. Heterocyclic Carbenes 7242 2.12. Zwitterionic Intermediates 7244 2.13. Si and Ge Analogues of Carbenes 7244 2.13.1. Silylene Addition to C 60 7244 2.13.2. Silylene Addition to C 707245 2.13.3. Germylene Addition to C 60 7245 3. Carbene Additions to Endohedral Metallofullerenes 7245 3.1. Endohedral Metallofullerenes 7245 3.2. M@C 2v (9)-C 82 7246 3.2.1. Photolysis of Diazirines 7246 3.2.2. Thermolysis of Diazomethanes 7248 3.2.3. In-Situ Generation of Diazo Compounds 7248 3.2.4. Metal-Catalyzed Reactions 7248 3.2.5. Zwitterionic Intermediates 7248 3.3. M@C s (6)-C 82 7249 3.4. M 2 @I h (7)-C 80 7249 3.4.1. Photolysis of Diazirines 7249 3.4.2. In-Situ Generation of Diazo Compounds 7251 3.5. M 2 @D 3h (5)-C 78 7251 3.5.1. Photolysis of Diazirines 7251 3.5.2. Thermolysis of Diazirines 7252 3.6. M 2 @D 2 (10611)-C 72 7252 3.7. M 3 N@I h( 7)-C 80 7252 3.7.1. In-Situ Generation of Diazo Compounds 7252 3.7.2. Silylenes 7253 3.8. Sc 2 C 2 @C 3v (8)-C 82 7254 3.9. Sc 2 C 2 @C 2v (5)-C 80 7254 3.10. Sc 3 C 2 @I h (7)-C 80 7255 3.11. Li@C 60 7255 4. Concluding Remarks 7256 Author Information 7257 Corresponding Author 7257 Notes 7257 Biographies 7257 Acknowledgments 7258 References 7258

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Section: Endohedral Metallofullerenesmentioning

confidence: 97%

“…Chlorophenyldiazirine 148 was applied for the functionalization of La@ C 2 v (9)-C 82 . EPR spectrum of the purified product suggested the existence of two inseparable isomers in a ratio of 57:43.…”

Section: Carbene Additions To Endohedral Metallofullerenesmentioning

confidence: 99%

Carbene Additions to Fullerenes

2013

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“…The reaction of La@C 2v -C 82 (Ad) with phenylchlorocarbene, which is formed by irradiation of 3-chloro-3-phenyldiazirine, also has the corresponding monoadducts. 38 The reaction of La@C s -C 82 with adamantylidene was also performed. 39 Because La@C s -C 82 has 44 non-equivalent carbons, its reactions might produce a larger number of regioisomers than those of La@C 2v -C 82 .…”

Section: Functionalization Of M@c 82mentioning

confidence: 99%

Current progress on the chemical functionalization and supramolecular chemistry of M@C82

Maeda

Tsuchiya

et al. 2011

Nanoscale

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Since the first discovery of fullerenes in 1985, the insertion of one or more atoms into a hollow fullerene cage has been attempted. Furthermore, synthesis and extraction of metallofullerene, La@C(n), were reported in 1991. Recent successful isolation and purification of metallofullerenes have facilitated the investigation of their chemical properties. This mini-review presents a summary of the recent progress of chemical functionalization and supramolecular chemistry of M@C(82). Selective functionalization and successful structural analysis of derivatives have revealed their chemical features arising from endohedral metal doping.

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“…We explored the reactivity of EMFs and found that reactions of EMFs with electrophilic carbenes proceed smoothly to afford the formation of corresponding EMF derivatives quantitatively [ 20 , 21 , 22 , 23 ]. These results encouraged us to synthesize functionalized EMF conjugates by such carbene addition.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition

et al. 2011

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Endohedral metallofullerene glycoconjugates were synthesized under mild conditions by carbene addition using appropriate glycosylidene-derived diazirine with La2@Ih-C80. NMR spectroscopic studies revealed that the glycoconjugate consists of two diastereomers of [6,6]-open mono-adducts. The electronic properties were characterized using Vis/NIR absorption spectroscopy and electrochemical measurements. This study demonstrates that glycosylidene carbene is useful to incorporate carbohydrate moieties onto endohedral metallofullerene surfaces.

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Chemical Modification of Endohedral Metallofullerene La@C₈₂ with 3-chloro-3-phenyldiazirine

Cited by 8 publications

References 20 publications

Carbene Additions to Fullerenes

Carbene Additions to Fullerenes

Current progress on the chemical functionalization and supramolecular chemistry of M@C82

Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition

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Chemical Modification of Endohedral Metallofullerene La@C82 with 3-chloro-3-phenyldiazirine

Cited by 8 publications

References 20 publications

Carbene Additions to Fullerenes

Carbene Additions to Fullerenes

Current progress on the chemical functionalization and supramolecular chemistry of M@C82

Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition

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Chemical Modification of Endohedral Metallofullerene La@C₈₂ with 3-chloro-3-phenyldiazirine