Prato, Maurizio

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orcid::0000-0002-8869-8612
  • Prato, Maurizio (4)
  • Prato, M (2)
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Author's Bibliography

Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics

Milić, Dragana; Prato, Maurizio

(Wiley-V C H Verlag Gmbh, Weinheim, 2010)

TY  - JOUR
AU  - Milić, Dragana
AU  - Prato, Maurizio
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1044
AB  - Two classes of unsymmetrical, orthogonally protected bis-fulleropyrrohdine amino acids have been prepared as models for fullerene-based peptidomimetics with the carbon sphere inserted into the peptide backbone Two successive [3+2] cycloadditions of azomethine ylides (thermally generated from formaldehyde and the corresponding orthogonally protected glycino-amines and -acids) to C(60) afforded NHFmoc/CO(2)tBu and NHBoc/CO(2)Me fulleropyrrolidine couples, offering the possibility of selective deprotection under both acidic and basic conditions In both classes of unsymmetrical bis-adducts, the distribution of all the trans (t(1)-t(4)) and equatorial (e' and e '') isomers was quite similar except. for the t(3) NHBoc/CO(2)Me compound, which rapidly decomposed during chromatography All compounds were characterized by UV/Vis, (1)H and (13)C NMR spectroscopy, and mass spectrometry
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics
IS  - 3
SP  - 476
EP  - 483
DO  - 10.1002/ejoc.200900791
ER  - 
@article{
author = "Milić, Dragana and Prato, Maurizio",
year = "2010",
abstract = "Two classes of unsymmetrical, orthogonally protected bis-fulleropyrrohdine amino acids have been prepared as models for fullerene-based peptidomimetics with the carbon sphere inserted into the peptide backbone Two successive [3+2] cycloadditions of azomethine ylides (thermally generated from formaldehyde and the corresponding orthogonally protected glycino-amines and -acids) to C(60) afforded NHFmoc/CO(2)tBu and NHBoc/CO(2)Me fulleropyrrolidine couples, offering the possibility of selective deprotection under both acidic and basic conditions In both classes of unsymmetrical bis-adducts, the distribution of all the trans (t(1)-t(4)) and equatorial (e' and e '') isomers was quite similar except. for the t(3) NHBoc/CO(2)Me compound, which rapidly decomposed during chromatography All compounds were characterized by UV/Vis, (1)H and (13)C NMR spectroscopy, and mass spectrometry",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics",
number = "3",
pages = "476-483",
doi = "10.1002/ejoc.200900791"
}
Milić, D.,& Prato, M.. (2010). Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(3), 476-483.
https://doi.org/10.1002/ejoc.200900791
Milić D, Prato M. Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics. in European Journal of Organic Chemistry. 2010;(3):476-483.
doi:10.1002/ejoc.200900791 .
Milić, Dragana, Prato, Maurizio, "Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics" in European Journal of Organic Chemistry, no. 3 (2010):476-483,
https://doi.org/10.1002/ejoc.200900791 . .
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Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene-peralkylated ferrocene dyad

Campidelli, Stephane; Severac, Marjorie; Scanu, David; Deschenaux, Robert; Vazquez, Ester; Milić, Dragana; Prato, Maurizio; Carano, Maurizio; Marcaccio, Massimo; Paolucci, Francesco; Rahman, G. M. Aminur; Guldi, Dirk M.

(Royal Soc Chemistry, Cambridge, 2008)

TY  - JOUR
AU  - Campidelli, Stephane
AU  - Severac, Marjorie
AU  - Scanu, David
AU  - Deschenaux, Robert
AU  - Vazquez, Ester
AU  - Milić, Dragana
AU  - Prato, Maurizio
AU  - Carano, Maurizio
AU  - Marcaccio, Massimo
AU  - Paolucci, Francesco
AU  - Rahman, G. M. Aminur
AU  - Guldi, Dirk M.
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/925
AB  - Two fullerene-peralkylated ferrocene derivatives were synthesized: (1) a liquid-crystalline dyad (compound 1) was obtained by introduction of nonamethyl ferrocene into a liquid-crystalline fullerene derivative and (2) a reference compound (compound 2) was synthesized by attachment of nonamethyl ferrocene to a fulleropyrrolidine. The liquid-crystalline dyad displayed an enantiotropic smectic A phase from 57 to 155 degrees C. Oxidation and reduction processes were investigated by cyclic voltammetry, and were in agreement with the electrochemical characteristics of the redox-active units (peralkylated ferrocene, fullerene, dendrimer). Photoinduced electron transfer from ferrocene derivative to fullerene was identified.
PB  - Royal Soc Chemistry, Cambridge
T2  - Journal of Materials Chemistry
T1  - Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene-peralkylated ferrocene dyad
VL  - 18
IS  - 13
SP  - 1504
EP  - 1509
DO  - 10.1039/b716806c
ER  - 
@article{
author = "Campidelli, Stephane and Severac, Marjorie and Scanu, David and Deschenaux, Robert and Vazquez, Ester and Milić, Dragana and Prato, Maurizio and Carano, Maurizio and Marcaccio, Massimo and Paolucci, Francesco and Rahman, G. M. Aminur and Guldi, Dirk M.",
year = "2008",
abstract = "Two fullerene-peralkylated ferrocene derivatives were synthesized: (1) a liquid-crystalline dyad (compound 1) was obtained by introduction of nonamethyl ferrocene into a liquid-crystalline fullerene derivative and (2) a reference compound (compound 2) was synthesized by attachment of nonamethyl ferrocene to a fulleropyrrolidine. The liquid-crystalline dyad displayed an enantiotropic smectic A phase from 57 to 155 degrees C. Oxidation and reduction processes were investigated by cyclic voltammetry, and were in agreement with the electrochemical characteristics of the redox-active units (peralkylated ferrocene, fullerene, dendrimer). Photoinduced electron transfer from ferrocene derivative to fullerene was identified.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Journal of Materials Chemistry",
title = "Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene-peralkylated ferrocene dyad",
volume = "18",
number = "13",
pages = "1504-1509",
doi = "10.1039/b716806c"
}
Campidelli, S., Severac, M., Scanu, D., Deschenaux, R., Vazquez, E., Milić, D., Prato, M., Carano, M., Marcaccio, M., Paolucci, F., Rahman, G. M. A.,& Guldi, D. M.. (2008). Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene-peralkylated ferrocene dyad. in Journal of Materials Chemistry
Royal Soc Chemistry, Cambridge., 18(13), 1504-1509.
https://doi.org/10.1039/b716806c
Campidelli S, Severac M, Scanu D, Deschenaux R, Vazquez E, Milić D, Prato M, Carano M, Marcaccio M, Paolucci F, Rahman GMA, Guldi DM. Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene-peralkylated ferrocene dyad. in Journal of Materials Chemistry. 2008;18(13):1504-1509.
doi:10.1039/b716806c .
Campidelli, Stephane, Severac, Marjorie, Scanu, David, Deschenaux, Robert, Vazquez, Ester, Milić, Dragana, Prato, Maurizio, Carano, Maurizio, Marcaccio, Massimo, Paolucci, Francesco, Rahman, G. M. Aminur, Guldi, Dirk M., "Photophysical, electrochemical, and mesomorphic properties of a liquid-crystalline [60]fullerene-peralkylated ferrocene dyad" in Journal of Materials Chemistry, 18, no. 13 (2008):1504-1509,
https://doi.org/10.1039/b716806c . .
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Liquid-crystalline bisadducts of [60]fullerene

Campidelli, Stephane; Vazquez, Ester; Milić, Dragana; Lenoble, Julie; Castellanos, Carmen Atienza; Sarova, Ginka; Guldi, Dirk M.; Deschenaux, Robert; Prato, Maurizio

(Amer Chemical Soc, Washington, 2006)

TY  - JOUR
AU  - Campidelli, Stephane
AU  - Vazquez, Ester
AU  - Milić, Dragana
AU  - Lenoble, Julie
AU  - Castellanos, Carmen Atienza
AU  - Sarova, Ginka
AU  - Guldi, Dirk M.
AU  - Deschenaux, Robert
AU  - Prato, Maurizio
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/802
AB  - A second-generation cyanobiphenyl-based dendrimer was used as a liquid-crystalline promoter to synthesize mesomorphic bisadducts of [60]fullerene. Liquid-crystalline trans-2, trans-3, and equatorial bisadducts were obtained by condensation of the liquid-crystalline promoter, which carries a carboxylic acid function, with the corresponding bisaminofullerene derivatives. A monoadduct of fullerene was also prepared for comparative purposes. All the compounds gave rise to smectic A phases. An additional mesophase, which could not be identified, was observed for the trans-2 derivative. The supramolecular organization of the monoadduct derivative is governed by steric constraints. Indeed, for efficient space filling, adequacy between the cross-sectional areas of fullerene (similar to 100 angstrom(2)) and of the mesogenic groups (similar to 22-25 angstrom(2) per mesogenic group) is required. As a consequence, the monoadduct forms a bilayered smectic A phase. The supramolecular organization of the bisadducts is essentially governed by the nature and structure of the mesogenic groups and dendritic core. Therefore, the bisadducts form monolayered smectic A phases. The title compounds are promising supramolecular materials as they combine the self-organizing behavior of liquid crystals with the properties of fullerene.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Liquid-crystalline bisadducts of [60]fullerene
VL  - 71
IS  - 20
SP  - 7603
EP  - 7610
DO  - 10.1021/jo0609576
ER  - 
@article{
author = "Campidelli, Stephane and Vazquez, Ester and Milić, Dragana and Lenoble, Julie and Castellanos, Carmen Atienza and Sarova, Ginka and Guldi, Dirk M. and Deschenaux, Robert and Prato, Maurizio",
year = "2006",
abstract = "A second-generation cyanobiphenyl-based dendrimer was used as a liquid-crystalline promoter to synthesize mesomorphic bisadducts of [60]fullerene. Liquid-crystalline trans-2, trans-3, and equatorial bisadducts were obtained by condensation of the liquid-crystalline promoter, which carries a carboxylic acid function, with the corresponding bisaminofullerene derivatives. A monoadduct of fullerene was also prepared for comparative purposes. All the compounds gave rise to smectic A phases. An additional mesophase, which could not be identified, was observed for the trans-2 derivative. The supramolecular organization of the monoadduct derivative is governed by steric constraints. Indeed, for efficient space filling, adequacy between the cross-sectional areas of fullerene (similar to 100 angstrom(2)) and of the mesogenic groups (similar to 22-25 angstrom(2) per mesogenic group) is required. As a consequence, the monoadduct forms a bilayered smectic A phase. The supramolecular organization of the bisadducts is essentially governed by the nature and structure of the mesogenic groups and dendritic core. Therefore, the bisadducts form monolayered smectic A phases. The title compounds are promising supramolecular materials as they combine the self-organizing behavior of liquid crystals with the properties of fullerene.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Liquid-crystalline bisadducts of [60]fullerene",
volume = "71",
number = "20",
pages = "7603-7610",
doi = "10.1021/jo0609576"
}
Campidelli, S., Vazquez, E., Milić, D., Lenoble, J., Castellanos, C. A., Sarova, G., Guldi, D. M., Deschenaux, R.,& Prato, M.. (2006). Liquid-crystalline bisadducts of [60]fullerene. in Journal of Organic Chemistry
Amer Chemical Soc, Washington., 71(20), 7603-7610.
https://doi.org/10.1021/jo0609576
Campidelli S, Vazquez E, Milić D, Lenoble J, Castellanos CA, Sarova G, Guldi DM, Deschenaux R, Prato M. Liquid-crystalline bisadducts of [60]fullerene. in Journal of Organic Chemistry. 2006;71(20):7603-7610.
doi:10.1021/jo0609576 .
Campidelli, Stephane, Vazquez, Ester, Milić, Dragana, Lenoble, Julie, Castellanos, Carmen Atienza, Sarova, Ginka, Guldi, Dirk M., Deschenaux, Robert, Prato, Maurizio, "Liquid-crystalline bisadducts of [60]fullerene" in Journal of Organic Chemistry, 71, no. 20 (2006):7603-7610,
https://doi.org/10.1021/jo0609576 . .
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A dendritic fullerene-porphyrin dyad

Campidelli, Stephane; Deschenaux, Robert; Swartz, Angela; Rahman, G. M. Aminur; Guldi, Dirk M.; Milić, Dragana; Vazquez, Ester; Prato, Maurizio

(Royal Soc Chemistry, Cambridge, 2006)

TY  - JOUR
AU  - Campidelli, Stephane
AU  - Deschenaux, Robert
AU  - Swartz, Angela
AU  - Rahman, G. M. Aminur
AU  - Guldi, Dirk M.
AU  - Milić, Dragana
AU  - Vazquez, Ester
AU  - Prato, Maurizio
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/816
AB  - We describe the synthesis, characterization and photophysical properties of a fullerene derivative whose structure includes a Zn-porphyrin and a second generation liquid-crystalline (LC) dendrimer. The size of the fullerene and porphyrin units with respect to the size of the LC dendrimer prevents the formation of liquid-crystalline phases. However, this system gives interesting photoinduced electron transfer phenomena. Compound I has been investigated by steady state and time resolved fluorescence as well as transient absorption spectroscopy in polar and apolar solvents. We demonstrate that the fluorescence of the porphyrin unit in I is quenched compared to the Zn-tetraphenylporphyrin used as reference. Femto- and picosecond transient absorption permit to identify the formation of a radical ion pair while nanosecond experiments allowed the determination of the charge recombination lifetimes.
PB  - Royal Soc Chemistry, Cambridge
T2  - Photochemical and Photobiological Sciences
T1  - A dendritic fullerene-porphyrin dyad
VL  - 5
IS  - 12
SP  - 1137
EP  - 1141
DO  - 10.1039/b610881d
ER  - 
@article{
author = "Campidelli, Stephane and Deschenaux, Robert and Swartz, Angela and Rahman, G. M. Aminur and Guldi, Dirk M. and Milić, Dragana and Vazquez, Ester and Prato, Maurizio",
year = "2006",
abstract = "We describe the synthesis, characterization and photophysical properties of a fullerene derivative whose structure includes a Zn-porphyrin and a second generation liquid-crystalline (LC) dendrimer. The size of the fullerene and porphyrin units with respect to the size of the LC dendrimer prevents the formation of liquid-crystalline phases. However, this system gives interesting photoinduced electron transfer phenomena. Compound I has been investigated by steady state and time resolved fluorescence as well as transient absorption spectroscopy in polar and apolar solvents. We demonstrate that the fluorescence of the porphyrin unit in I is quenched compared to the Zn-tetraphenylporphyrin used as reference. Femto- and picosecond transient absorption permit to identify the formation of a radical ion pair while nanosecond experiments allowed the determination of the charge recombination lifetimes.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Photochemical and Photobiological Sciences",
title = "A dendritic fullerene-porphyrin dyad",
volume = "5",
number = "12",
pages = "1137-1141",
doi = "10.1039/b610881d"
}
Campidelli, S., Deschenaux, R., Swartz, A., Rahman, G. M. A., Guldi, D. M., Milić, D., Vazquez, E.,& Prato, M.. (2006). A dendritic fullerene-porphyrin dyad. in Photochemical and Photobiological Sciences
Royal Soc Chemistry, Cambridge., 5(12), 1137-1141.
https://doi.org/10.1039/b610881d
Campidelli S, Deschenaux R, Swartz A, Rahman GMA, Guldi DM, Milić D, Vazquez E, Prato M. A dendritic fullerene-porphyrin dyad. in Photochemical and Photobiological Sciences. 2006;5(12):1137-1141.
doi:10.1039/b610881d .
Campidelli, Stephane, Deschenaux, Robert, Swartz, Angela, Rahman, G. M. Aminur, Guldi, Dirk M., Milić, Dragana, Vazquez, Ester, Prato, Maurizio, "A dendritic fullerene-porphyrin dyad" in Photochemical and Photobiological Sciences, 5, no. 12 (2006):1137-1141,
https://doi.org/10.1039/b610881d . .
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Liquid-crystalline fullerene-ferrocene dyads

Campidelli, S; Vazquez, E; Milić, Dragana; Prato, M; Barbera, J; Guldi, DM; Marcaccio, M; Paolucci, D; Paolucci, F; Deschenaux, R

(Royal Soc Chemistry, Cambridge, 2004)

TY  - JOUR
AU  - Campidelli, S
AU  - Vazquez, E
AU  - Milić, Dragana
AU  - Prato, M
AU  - Barbera, J
AU  - Guldi, DM
AU  - Marcaccio, M
AU  - Paolucci, D
AU  - Paolucci, F
AU  - Deschenaux, R
PY  - 2004
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/634
AB  - The 1,3-dipolar cycloaddition reaction was used to assemble fullerene, ferrocene and a second-generation liquid-crystalline cyanobiphenyl-based dendrimer. The targeted compound displayed an enantiotropic smectic A phase from 40 to 135degreesC. The d-layer spacing was determined by X-ray diffraction, and was found to be independent of temperature with a value of 95 Angstrom. Molecular modeling and structural considerations suggested partial bilayer organization of the mesogenic molecular units within the smectic layers. Oxidation or reduction processes of the basic components (ferrocene, fullerene, dendrimer) were investigated by electrochemical techniques, and were in agreement with the structure. Photoinduced electron transfer from ferrocene to fullerene was identified, most likely with a "through space" mechanism.
PB  - Royal Soc Chemistry, Cambridge
T2  - Journal of Materials Chemistry
T1  - Liquid-crystalline fullerene-ferrocene dyads
VL  - 14
IS  - 8
SP  - 1266
EP  - 1272
DO  - 10.1039/b316085h
ER  - 
@article{
author = "Campidelli, S and Vazquez, E and Milić, Dragana and Prato, M and Barbera, J and Guldi, DM and Marcaccio, M and Paolucci, D and Paolucci, F and Deschenaux, R",
year = "2004",
abstract = "The 1,3-dipolar cycloaddition reaction was used to assemble fullerene, ferrocene and a second-generation liquid-crystalline cyanobiphenyl-based dendrimer. The targeted compound displayed an enantiotropic smectic A phase from 40 to 135degreesC. The d-layer spacing was determined by X-ray diffraction, and was found to be independent of temperature with a value of 95 Angstrom. Molecular modeling and structural considerations suggested partial bilayer organization of the mesogenic molecular units within the smectic layers. Oxidation or reduction processes of the basic components (ferrocene, fullerene, dendrimer) were investigated by electrochemical techniques, and were in agreement with the structure. Photoinduced electron transfer from ferrocene to fullerene was identified, most likely with a "through space" mechanism.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Journal of Materials Chemistry",
title = "Liquid-crystalline fullerene-ferrocene dyads",
volume = "14",
number = "8",
pages = "1266-1272",
doi = "10.1039/b316085h"
}
Campidelli, S., Vazquez, E., Milić, D., Prato, M., Barbera, J., Guldi, D., Marcaccio, M., Paolucci, D., Paolucci, F.,& Deschenaux, R.. (2004). Liquid-crystalline fullerene-ferrocene dyads. in Journal of Materials Chemistry
Royal Soc Chemistry, Cambridge., 14(8), 1266-1272.
https://doi.org/10.1039/b316085h
Campidelli S, Vazquez E, Milić D, Prato M, Barbera J, Guldi D, Marcaccio M, Paolucci D, Paolucci F, Deschenaux R. Liquid-crystalline fullerene-ferrocene dyads. in Journal of Materials Chemistry. 2004;14(8):1266-1272.
doi:10.1039/b316085h .
Campidelli, S, Vazquez, E, Milić, Dragana, Prato, M, Barbera, J, Guldi, DM, Marcaccio, M, Paolucci, D, Paolucci, F, Deschenaux, R, "Liquid-crystalline fullerene-ferrocene dyads" in Journal of Materials Chemistry, 14, no. 8 (2004):1266-1272,
https://doi.org/10.1039/b316085h . .
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Synthesis and water solubility of novel fullerene bisadduct derivatives

Bosi, S; Feruglio, L; Milić, Dragana; Prato, M

(Wiley-V C H Verlag Gmbh, Weinheim, 2003)

TY  - JOUR
AU  - Bosi, S
AU  - Feruglio, L
AU  - Milić, Dragana
AU  - Prato, M
PY  - 2003
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/164
AB  - The synthesis of four classes of bisadduct derivatives of C-60 is reported. The solubility of the new compounds in aqueous solvents is enhanced and is among the highest ever reported for fullerene derivatives. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Synthesis and water solubility of novel fullerene bisadduct derivatives
IS  - 24
SP  - 4741
EP  - 4747
DO  - 10.1002/ejoc.200300494
ER  - 
@article{
author = "Bosi, S and Feruglio, L and Milić, Dragana and Prato, M",
year = "2003",
abstract = "The synthesis of four classes of bisadduct derivatives of C-60 is reported. The solubility of the new compounds in aqueous solvents is enhanced and is among the highest ever reported for fullerene derivatives. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Synthesis and water solubility of novel fullerene bisadduct derivatives",
number = "24",
pages = "4741-4747",
doi = "10.1002/ejoc.200300494"
}
Bosi, S., Feruglio, L., Milić, D.,& Prato, M.. (2003). Synthesis and water solubility of novel fullerene bisadduct derivatives. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(24), 4741-4747.
https://doi.org/10.1002/ejoc.200300494
Bosi S, Feruglio L, Milić D, Prato M. Synthesis and water solubility of novel fullerene bisadduct derivatives. in European Journal of Organic Chemistry. 2003;(24):4741-4747.
doi:10.1002/ejoc.200300494 .
Bosi, S, Feruglio, L, Milić, Dragana, Prato, M, "Synthesis and water solubility of novel fullerene bisadduct derivatives" in European Journal of Organic Chemistry, no. 24 (2003):4741-4747,
https://doi.org/10.1002/ejoc.200300494 . .
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