61,61‐Bis(trimethylsilylbutadiinyl)‐1,2‐dihydro‐1,2‐methanofulleren[60]: Kristallstruktur bei 100 K und elektrochemische Umwandlung in ein leitfähiges Polymer

Anderson, Harry L.; Boudon, Corinne; Diederich, François; Gisselbrecht, Jean‐Paul; Gross, Maurice; Seiler, Paul

doi:10.1002/ange.19941061524

Cited by 26 publications

(2 citation statements)

References 34 publications

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“…~~-OM~ (I) The increased bond length between the two bridged C atoms, C1 and C2, of 1.597 (4)A, is in good agreement with comparable bond lengths found for methanofullerenes [1.574 (3)-1.614 (7) A (Anderson, Boudon, Diederich, Gisselbrecht, Gross & Seiler, 1994;Osterodt, Nieger & V6gtle, 1994;Paulus & Bingel, 1995 (Johnson, 1971) drawing of the asymmetric unit showing the crystallographic numbering scheme (50% probability displacement ellipsoids). All five-and six-membered rings of the C60 sphere, except those containing C1 and C2, are planar, with average distances of the atoms from the least-squares planes of 0.005 (2) and 0.006 (2) ,~, respectively.…”

Section: H~/~~~ Cs2supporting

confidence: 75%

1,2-[3,4-Dihydro-2-(4-methoxyphenyl)-2H-pyrrolo][60]fullerene Carbon Disulfide

Ramm¹,

Luger²,

Averdung³

et al. 1996

Acta Crystallogr C

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Section: H~/~~~ Cs2supporting

confidence: 75%

1,2-[3,4-Dihydro-2-(4-methoxyphenyl)-2H-pyrrolo][60]fullerene Carbon Disulfide

Ramm¹,

Luger²,

Averdung³

et al. 1996

Acta Crystallogr C

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“…[32] By contrast, in CH 2 Cl 2 (vs SCE) the first reduction of both Si ± C 60 (À 0.520 V, rev) and the fullerene units of Si-C 60 -Cu (À 0.6 V, irrev) appear in the range typical of C 60 monoadducts. [6,33] As previously observed for various bis(butadiynyl)methanofullerene derivatives, [34] Si-C 60 -Cu undergoes reductive electrochemical polymerization during iterative cyclic voltammetry to give an insoluble, insulating film on the platinum cathode surface.…”

Section: Electrochemistrymentioning

confidence: 79%

A Copper( I )‐Complexed Rotaxane with Two Fullerene Stoppers: Synthesis, Electrochemistry, and Photoinduced Processes

Armaroli

Diederich

Dietrich‐Buchecker

et al. 1998

Chemistry A European J

140

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A rotaxane made from a bisphenanthroline Cu I complex and two C 60 units acting as stoppers has been synthesized. Electrochemical, spectroscopic and photophysical properties of the individual components, a methanofullerene and a Cu I catenate, were determined. The properties of the methanofullerene were also compared with those of plain C 60 and rationalized with the aid of semiempirical calculations. The changes in the photophysical properties detected in the rotaxane with respect to the models were assigned to the occurrence of intramolecular processes. The excited singlet state localized on the fullerene and the MLCT excited state centred on the Cu I complex are both quenched. Deactivation of the fullerene excited singlet state occurs by energy transfer to the Cu I -complex moiety, which competes with intersystem crossing to triplet fullerene, whereas the Cu I -complex excited state is mainly quenched by electron transfer to form the charge-separated state consisting of the oxidized metal centre [Cu(phen) 2 ] 2 and the fullerene radical anion. The fullerene triplet, formed in reduced yield with respect to the model, is also quenched by electron transfer to the same charge-separated state. The ability of both model components to sensitize singlet oxygen is completely suppressed in the rotaxane. The occurrence of a fast back-electron-transfer reaction is postulated, as spectroscopic detection of the charge-separated state has not been achieved.

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Elektrochemische Synthese eines redoxaktiven Polymers aus Buckminsterfullerenepoxid

et al. 1995

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ZUSCHRIFTEN die begiinstigte si-Kupplung rnit 4 festgehalten. Die Diastereoselektivitat mit dem Auxiliar B und C ist gering, offenbar ist hier die Carbonylgruppe und nicht der Benzylrest des Auxiliars synstlndig zum radikalischen C-Atom orientiert, so daB sich hier die Seitendifferenzierung kaum ausbilden kann. Erwartungsge-mlB steigt die Diastereoselektivitiit der Kupplung mit zunehmender GroBe des Coradikals an (Nr. 7 < 8 < 9 < 10).Da radikalische Kupplungen sehr s~h n e l l~~'~, d. h. mit sehr kleiner Aktivierungsenergie, ablaufen, ist nach dem Hammond-Prinzip ein sehr fruher Ubergangszustand zu erwarten, in dem die sterische Wechselwirkung zwischen den Radikalen 3 und 4 noch wenig ausgepragt ist. Trotzdem lassen sich rnit den in rddikalischen Additionen bewahrten Auxiliaren und voluminosen Coradikalen auch in intermolekularen radikalischen Kupplungen bemerkenswerte Diastereoselektivitaten erreichen. ExprrimentellesSk,6k:203mg(0.568mmol) Ihund660mg(5.68mmol)2cwurdenin 10-13mL wasserfreiem Methanol gelost. nut 0.31 mL 1 M KOH-Losung in wasserfreiem Methanol zu 5 % neutralisiert und in einer Umlaufzelle rnit einer Stahlkathode, einer Platinanode (4 em2) (Elektrodenabstand: 0.5 mm) bei einer Stromdichte von 600 rnAcrn-, und einer Temperatur von 30-35 "C elektrolysiert. Mit dem Erreichen des pH-Werts X 9 wurde die Elektrolyse abgebrochen, das Losungsmittel abdestilliert, der Ruckstand in Diethylether aufgenommen, mit gesiittigter Natriumhydrogencarbonat-L6sung gewaschen und getrocknet (MgSO,). Der Diastereomerenuberschufl wurde im Ruckstand durch Kapillargaschromatographie bestimmt und die Diastereomere flashchromatographisch und iiber HPLC isoliert.

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61,61‐Bis(trimethylsilylbutadiinyl)‐1,2‐dihydro‐1,2‐methanofulleren[60]: Kristallstruktur bei 100 K und elektrochemische Umwandlung in ein leitfähiges Polymer

Cited by 26 publications

References 34 publications

1,2-[3,4-Dihydro-2-(4-methoxyphenyl)-2H-pyrrolo][60]fullerene Carbon Disulfide

1,2-[3,4-Dihydro-2-(4-methoxyphenyl)-2H-pyrrolo][60]fullerene Carbon Disulfide

A Copper( I )‐Complexed Rotaxane with Two Fullerene Stoppers: Synthesis, Electrochemistry, and Photoinduced Processes

Elektrochemische Synthese eines redoxaktiven Polymers aus Buckminsterfullerenepoxid

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