Synthesis and Electrochemical Properties of New C60-Acceptor and -Donor Dyads

Synthesis and fluorescence properties of [60] and [70]fullerene–coumarin dyads: Efficient dipole–dipole resonance energy transfer from coumarin to fullerene

“…The covalent functionalization of the fullerenes has developed rapidly in the last few years to the extent that now C 60 , which is by far the most studied fullerene, can be considered a versatile building block in organic chemistry. 1 Over the past decade, a large number of C 60 -based donor-acceptor dyads and more complex polyads, in which C 60 is covalently linked to photoactive groups, were obtained, aiming at exploring their excited-state donor-acceptor interactions, including photoinduced electron [1][2][3][4][5][6][7][8][9] and energy [9][10][11][12][13][14][15][16][17][18][19][20][21][22] transfer.…”

“…7,[23][24][25][26] For this purpose, several synthetic methodologies have been developed which allow covalent linkages of C 60 with other photo-and electro-active molecules. 3,4 Different donors and linkers to C 60 have been used. In fact, the length, chemical constitution or the presence of rigid or saturated hydrocarbon bridges is known to play an important role in the electronic coupling between the donor and the acceptor chromophores.…”

Instability of [60]fullerene anions in dichloromethane: a synthetic avenue to C60>(CH2)n methanofullerenes

“…Notes and references † Electrochemistry: details of the experimental electrochemical set-up for the CV, OSWV and bulk electrolysis measurements have been described elsewhere. 14 Briefly, electrochemical measurements were performed using a BAS 100W Electrochemical Analyzer (Bioanalytical systems). An electrochemical cell designed to carry out CV, OSWV and bulk electrolysis under high vacuum was used.…”

Adduct removal from methanofullerenes via reductive electrochemistry

“…Further reaction of 2-diazoindan-1,3-dione with C 60 in ODCB (o-dichlorobenzene) at 120 °C for 4 h afforded spiromethanofullerene 3 10 in 33% yield (62% based on consumed C 60 ). Compound 3 showed the presence of the carbonyl groups as a single signal at d 191.7 in the 13 C NMR spectrum, which shows the presence of 17 signals, suggesting a C 2v symmetry. Spiromethanofullerene 4 was obtained from diphenylcyclopropenone in two steps, by formation of the tosylhydrazone and further in situ generation of the intermediate diazo compound under basic conditions, 11 which reacted with C 60 by heating in ODCB to lead to 4 in 20% yield (46% based on consumed C 60 ).…”

“…2 and Table 1). 12,13 The methanofullerenes 1 and 2 both exhibit, besides several reversible electrochemical processes, an irreversible electrochemical reduction wave between the first and third reductions. Compound 3 undergoes a two-electron reduction, followed by two one- electron reductions.…”