Synthesis and properties of pyrazolino[60]fullerene-donor systems

The Isoindazole Nucleus as a Donor in Fullerene-Based Dyads. Evidence for Electron Transfer

“…Four of them ( E 1 red , E 2 red , E 4 red , and E 6 red ) are quasi-reversible, corresponding to the fullerene core, while the other two irreversible CV peaks such as E 3 red are assigned to the p -nitrophenyl moiety and E 5 red to the isoindazole group by comparison with those of the starting hydrazones 3a − c . Similar to other pyrazolino[60]fullerene derivatives, , the first reduction potentials ( E 1 red ) are analogous to that of pure C 60 and shifted to more positive values in comparison to other fullerene derivatives due to the − I effect of the pyrazoline ring. The first reduction potential is more shifted toward a positive value in 4c (30 mV with respect to C 60 ) as a consequence of the presence of the electron-withdrawing cyano group.…”

The Isoindazole Nucleus as a Donor in Fullerene-Based Dyads. Evidence for Electron Transfer

“…Four of them ( E 1 red , E 2 red , E 4 red , and E 6 red ) are quasi-reversible, corresponding to the fullerene core, while the other two irreversible CV peaks such as E 3 red are assigned to the p -nitrophenyl moiety and E 5 red to the isoindazole group by comparison with those of the starting hydrazones 3a − c . Similar to other pyrazolino[60]fullerene derivatives, , the first reduction potentials ( E 1 red ) are analogous to that of pure C 60 and shifted to more positive values in comparison to other fullerene derivatives due to the − I effect of the pyrazoline ring. The first reduction potential is more shifted toward a positive value in 4c (30 mV with respect to C 60 ) as a consequence of the presence of the electron-withdrawing cyano group.…”

Through-space communication in a TTF–C 60 –TTF triad

“…5b It was deduced that the charge separation process This journal is c the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2007 took place via the 3 C 60 * moiety in these solvents. 5b On the other hand, TTF-(spacer)-PzC 60 -(spacer)-TTF (7), in the present study, showed faster fluorescence quenching rates in non-polar and less-polar solvents rather than in highly polar solvents. Therefore, the charge separation process of triad 7 takes place predominantly via the 1 C 60 * moiety, not via the 3 C 60 * moiety.…”

Self-Assembly-Directed Organization of a Fullerene–Bisporphyrin into Supramolecular Giant Donut Structures for Excited-State Charge Stabilization

“…Figure a shows representative CVs of compounds 1 and C 60 in o -dichloro­benzene:acetonitrile (4:1 v/v), and the measured redox potentials are summarized in Table S4 along with additional CVs and OSWVs. Both compounds 1 and 2 exhibit two reduction and two oxidation processes within the accessible potential window, displaying slightly better electron affinities ( E 1 red = −1.01 V for 1 and −1.00 V for 2 ) than pristine C 60 (−1.03 V) as described for other pyrazolino­fullerene derivatives . In the anodic side of the voltammograms, the first oxidation process is associated with the porphyrin moieties and appears at +0.29 and +0.30 V for 1 and 2 , respectively.…”

The Isoindazole Nucleus as a Donor in Fullerene-Based Dyads. Evidence for Electron Transfer

“…Four of them ( E 1 red , E 2 red , E 4 red , and E 6 red ) are quasi-reversible, corresponding to the fullerene core, while the other two irreversible CV peaks such as E 3 red are assigned to the p -nitrophenyl moiety and E 5 red to the isoindazole group by comparison with those of the starting hydrazones 3a − c . Similar to other pyrazolino[60]fullerene derivatives, , the first reduction potentials ( E 1 red ) are analogous to that of pure C 60 and shifted to more positive values in comparison to other fullerene derivatives due to the − I effect of the pyrazoline ring. The first reduction potential is more shifted toward a positive value in 4c (30 mV with respect to C 60 ) as a consequence of the presence of the electron-withdrawing cyano group.…”

Through-space communication in a TTF–C 60 –TTF triad

“…5b It was deduced that the charge separation process This journal is c the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2007 took place via the 3 C 60 * moiety in these solvents. 5b On the other hand, TTF-(spacer)-PzC 60 -(spacer)-TTF (7), in the present study, showed faster fluorescence quenching rates in non-polar and less-polar solvents rather than in highly polar solvents. Therefore, the charge separation process of triad 7 takes place predominantly via the 1 C 60 * moiety, not via the 3 C 60 * moiety.…”

Self-Assembly-Directed Organization of a Fullerene–Bisporphyrin into Supramolecular Giant Donut Structures for Excited-State Charge Stabilization

“…Figure a shows representative CVs of compounds 1 and C 60 in o -dichloro­benzene:acetonitrile (4:1 v/v), and the measured redox potentials are summarized in Table S4 along with additional CVs and OSWVs. Both compounds 1 and 2 exhibit two reduction and two oxidation processes within the accessible potential window, displaying slightly better electron affinities ( E 1 red = −1.01 V for 1 and −1.00 V for 2 ) than pristine C 60 (−1.03 V) as described for other pyrazolino­fullerene derivatives . In the anodic side of the voltammograms, the first oxidation process is associated with the porphyrin moieties and appears at +0.29 and +0.30 V for 1 and 2 , respectively.…”

The Isoindazole Nucleus as a Donor in Fullerene-Based Dyads. Evidence for Electron Transfer

“…Four of them ( E 1 red , E 2 red , E 4 red , and E 6 red ) are quasi-reversible, corresponding to the fullerene core, while the other two irreversible CV peaks such as E 3 red are assigned to the p -nitrophenyl moiety and E 5 red to the isoindazole group by comparison with those of the starting hydrazones 3a − c . Similar to other pyrazolino[60]fullerene derivatives, , the first reduction potentials ( E 1 red ) are analogous to that of pure C 60 and shifted to more positive values in comparison to other fullerene derivatives due to the − I effect of the pyrazoline ring. The first reduction potential is more shifted toward a positive value in 4c (30 mV with respect to C 60 ) as a consequence of the presence of the electron-withdrawing cyano group.…”

Through-space communication in a TTF–C 60 –TTF triad

“…5b It was deduced that the charge separation process This journal is c the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2007 took place via the 3 C 60 * moiety in these solvents. 5b On the other hand, TTF-(spacer)-PzC 60 -(spacer)-TTF (7), in the present study, showed faster fluorescence quenching rates in non-polar and less-polar solvents rather than in highly polar solvents. Therefore, the charge separation process of triad 7 takes place predominantly via the 1 C 60 * moiety, not via the 3 C 60 * moiety.…”

Self-Assembly-Directed Organization of a Fullerene–Bisporphyrin into Supramolecular Giant Donut Structures for Excited-State Charge Stabilization

“…Figure a shows representative CVs of compounds 1 and C 60 in o -dichloro­benzene:acetonitrile (4:1 v/v), and the measured redox potentials are summarized in Table S4 along with additional CVs and OSWVs. Both compounds 1 and 2 exhibit two reduction and two oxidation processes within the accessible potential window, displaying slightly better electron affinities ( E 1 red = −1.01 V for 1 and −1.00 V for 2 ) than pristine C 60 (−1.03 V) as described for other pyrazolino­fullerene derivatives . In the anodic side of the voltammograms, the first oxidation process is associated with the porphyrin moieties and appears at +0.29 and +0.30 V for 1 and 2 , respectively.…”