Hiding and Recovering Electrons in a Dimetallic Endohedral Fullerene: Air-Stable Products from Radical Additions

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10292889" target="_blank" >RIV/00216208:11310/15:10292889 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1021/ja509956y" target="_blank" >http://dx.doi.org/10.1021/ja509956y</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/ja509956y" target="_blank" >10.1021/ja509956y</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Hiding and Recovering Electrons in a Dimetallic Endohedral Fullerene: Air-Stable Products from Radical Additions

Popis výsledku v původním jazyce

Fullerenyl radicals can be generated by addition of a free radical to a fullerene surface, by nucleophilic addition followed by one-electron oxidation, or by thermal dissociation of singly bonded fullerene dimers. However, fullerenyl radicals are usuallyvery reactive and generally cannot be isolated. On the contrary, we have found that the reactions of the dimetallic endofullerenes, La-2@I-h-C-80 and La-2@D-5h-C-80, with 3-chloro-5,6-diphenyltriazine resulted in mono-addition of the triazinyl radical to the fullerene cages to yield isolable fullerenyl radicals. The unusual stability of these fullerenyl radicals arises from the confinement of the unpaired electron to an internal, metalmetal bonding orbital. Accordingly, the fullerene cage protects theradical center from other reactive species. Furthermore, we demonstrate that the fullerenyl radical adduct of La-2@I-h-C-80 reacts with toluene to afford additional benzylation. Interestingly, the benzylated derivative is diamagnetic in s

Název v anglickém jazyce

Hiding and Recovering Electrons in a Dimetallic Endohedral Fullerene: Air-Stable Products from Radical Additions

Popis výsledku anglicky

Fullerenyl radicals can be generated by addition of a free radical to a fullerene surface, by nucleophilic addition followed by one-electron oxidation, or by thermal dissociation of singly bonded fullerene dimers. However, fullerenyl radicals are usuallyvery reactive and generally cannot be isolated. On the contrary, we have found that the reactions of the dimetallic endofullerenes, La-2@I-h-C-80 and La-2@D-5h-C-80, with 3-chloro-5,6-diphenyltriazine resulted in mono-addition of the triazinyl radical to the fullerene cages to yield isolable fullerenyl radicals. The unusual stability of these fullerenyl radicals arises from the confinement of the unpaired electron to an internal, metalmetal bonding orbital. Accordingly, the fullerene cage protects theradical center from other reactive species. Furthermore, we demonstrate that the fullerenyl radical adduct of La-2@I-h-C-80 reacts with toluene to afford additional benzylation. Interestingly, the benzylated derivative is diamagnetic in s

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CF - Fyzikální chemie a teoretická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of the American Chemical Society

ISSN

0002-7863

e-ISSN

—

Svazek periodika

137

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

232-238

Kód UT WoS článku

000348483500050

EID výsledku v databázi Scopus

2-s2.0-84921058882