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Title: Endohedral fullerenes: Synthesis, isolation, mono- and bis -functionalization

Abstract

Here, in this paper, we present a short overview of the contribution of our research group to the discovery, functionalization and characterization of unprecedented endohedral fullerenes. We also report a comprehensive study of regioselective bis-1,3-dipolar cycloadditions to cluster endohedral fullerenes M3N@Ih-C80 (M = Lu, Y and Er) and the spectroscopic characterization of the new bis-adducts obtained.

Authors:
 [1];  [2];  [3];  [4]
  1. University of Texas at El Paso, El Paso, TX (United States). Department of Chemistry; Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States). Physical and Life Sciences
  2. University of Texas at El Paso, El Paso, TX (United States); Istituto Italiano di Tecnologia (Italy). Nano Carbon Materials Laboratory; University of Genova (Italy). Department of Chemistry and Industrial Chemistry
  3. Indiana-Purdue University at Fort Wayne, Fort Wayne, IN (United States). Department of Chemistry
  4. University of Texas at El Paso, El Paso, TX (United States). Department of Chemistry
Publication Date:
Research Org.:
Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1409946
Report Number(s):
LLNL-JRNL-720246
Journal ID: ISSN 0020-1693
Grant/Contract Number:  
AC52-07NA27344
Resource Type:
Accepted Manuscript
Journal Name:
Inorganica Chimica Acta
Additional Journal Information:
Journal Volume: 468; Journal Issue: C; Journal ID: ISSN 0020-1693
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY

Citation Formats

Cerón, Maira R., Maffeis, Viviana, Stevenson, Steven, and Echegoyen, Luis. Endohedral fullerenes: Synthesis, isolation, mono- and bis -functionalization. United States: N. p., 2017. Web. doi:10.1016/j.ica.2017.03.040.
Cerón, Maira R., Maffeis, Viviana, Stevenson, Steven, & Echegoyen, Luis. Endohedral fullerenes: Synthesis, isolation, mono- and bis -functionalization. United States. https://doi.org/10.1016/j.ica.2017.03.040
Cerón, Maira R., Maffeis, Viviana, Stevenson, Steven, and Echegoyen, Luis. Wed . "Endohedral fullerenes: Synthesis, isolation, mono- and bis -functionalization". United States. https://doi.org/10.1016/j.ica.2017.03.040. https://www.osti.gov/servlets/purl/1409946.
@article{osti_1409946,
title = {Endohedral fullerenes: Synthesis, isolation, mono- and bis -functionalization},
author = {Cerón, Maira R. and Maffeis, Viviana and Stevenson, Steven and Echegoyen, Luis},
abstractNote = {Here, in this paper, we present a short overview of the contribution of our research group to the discovery, functionalization and characterization of unprecedented endohedral fullerenes. We also report a comprehensive study of regioselective bis-1,3-dipolar cycloadditions to cluster endohedral fullerenes M3N@Ih-C80 (M = Lu, Y and Er) and the spectroscopic characterization of the new bis-adducts obtained.},
doi = {10.1016/j.ica.2017.03.040},
journal = {Inorganica Chimica Acta},
number = C,
volume = 468,
place = {United States},
year = {Wed Mar 29 00:00:00 EDT 2017},
month = {Wed Mar 29 00:00:00 EDT 2017}
}

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Works referenced in this record:

C60: Buckminsterfullerene
journal, November 1985

  • Kroto, H. W.; Heath, J. R.; O'Brien, S. C.
  • Nature, Vol. 318, Issue 6042
  • DOI: 10.1038/318162a0

Solid C60: a new form of carbon
journal, September 1990

  • Krätschmer, W.; Lamb, Lowell D.; Fostiropoulos, K.
  • Nature, Vol. 347, Issue 6291
  • DOI: 10.1038/347354a0

Electrochemical detection of C606- and C706-: Enhanced stability of fullerides in solution
journal, May 1992

  • Xie, Qingshan; Perez-Cordero, Eduardo; Echegoyen, Luis
  • Journal of the American Chemical Society, Vol. 114, Issue 10
  • DOI: 10.1021/ja00036a056

Electrochemically-reversible, single-electron oxidation of C60 and C70
journal, October 1993

  • Xie, Qingshan; Arias, Francisco; Echegoyen, Luis
  • Journal of the American Chemical Society, Vol. 115, Issue 21
  • DOI: 10.1021/ja00074a066

Reversible Fullerene Electrochemistry: Correlation with the HOMO-LUMO Energy Difference for C60, C70, C76, C78, and C84
journal, July 1995

  • Yang, Yifan; Arias, Francisco; Echegoyen, Luis
  • Journal of the American Chemical Society, Vol. 117, Issue 29
  • DOI: 10.1021/ja00134a027

Redox Characteristics of Covalent Derivatives of the Higher Fullerenes C 70 , C 76 , and C 78
journal, August 1998

  • Boudon, Corinne; Gisselbrecht, Jean-Paul; Gross, Maurice
  • Journal of the American Chemical Society, Vol. 120, Issue 31
  • DOI: 10.1021/ja981334f

Kinetic Effects in the Electrochemistry of Fullerene Derivatives at Very Negative Potentials
journal, July 1994

  • Arias, Francisco; Xie, Qingshan; Echegoyen, Luis
  • Journal of the American Chemical Society, Vol. 116, Issue 14
  • DOI: 10.1021/ja00093a045

Methanofullerenes and Methanofulleroids Have Different Electrochemical Behavior at Negative Potentials
journal, February 1995

  • Arias, Francisco; Echegoyen, Luis; Wilson, Stephen R.
  • Journal of the American Chemical Society, Vol. 117, Issue 4
  • DOI: 10.1021/ja00109a029

Walk on the Sphere:  Electrochemically Induced Isomerization of C 60 Bis-adducts by Migration of Di(alkoxycarbonyl)methano Bridges
journal, August 1998

  • Kessinger, Roland; Gómez-López, Marcos; Boudon, Corinne
  • Journal of the American Chemical Society, Vol. 120, Issue 33
  • DOI: 10.1021/ja981387x

Electrochemistry of Fullerenes and Their Derivatives
journal, September 1998

  • Echegoyen, Luis; Echegoyen, Lourdes E.
  • Accounts of Chemical Research, Vol. 31, Issue 9, p. 593-601
  • DOI: 10.1021/ar970138v

Supramolecular Fullerene Chemistry: A Comprehensive Study of Cyclophane-Type Mono- and Bis-Crown Ether Conjugates of C70
journal, July 2002


Recent progress in the synthesis of regio-isomerically pure bis -adducts of empty and endohedral fullerenes: Fullerene bis -Adducts
journal, May 2016

  • Cerón, Maira R.; Echegoyen, Luis
  • Journal of Physical Organic Chemistry, Vol. 29, Issue 11
  • DOI: 10.1002/poc.3563

A new route for the selective synthesis of [6,6]-methanofullerenes. Electrosynthesis of C61HCMe3 and C61HCN
journal, January 1996

  • Boulas, Pierre L.; Zuo, Yuhong; Echegoyen, Luis
  • Chemical Communications, Issue 13
  • DOI: 10.1039/cc9960001547

Chemistry of C84: Separation of Three Constitutional Isomers and Optical Resolution ofD2-C84 by Using the “Bingel-Retro-Bingel” Strategy
journal, June 1999


Selective Electrolytic Removal of Bis(alkoxycarbonyl)methano Addends from C60 Bis-adducts and Electrochemical Stability of C70 Derivatives
journal, June 2000


Selective Electrochemical Retro-Cycloaddition Reaction of Pyrrolidinofullerenes
journal, November 2006

  • Lukoyanova, Olena; Cardona, Claudia M.; Altable, Margarita
  • Angewandte Chemie International Edition, Vol. 45, Issue 44
  • DOI: 10.1002/anie.200602431

Lanthanum complexes of spheroidal carbon shells
journal, December 1985

  • Heath, J. R.; O'Brien, S. C.; Zhang, Q.
  • Journal of the American Chemical Society, Vol. 107, Issue 25
  • DOI: 10.1021/ja00311a102

Fullerenes with metals inside
journal, October 1991

  • Chai, Yan; Guo, Ting; Jin, Changming
  • The Journal of Physical Chemistry, Vol. 95, Issue 20
  • DOI: 10.1021/j100173a002

Erratum: Small-bandgap endohedral metallofullerenes in high yield and purity
journal, December 1999

  • Stevenson, S.; Rice, G.; Glass, T.
  • Nature, Vol. 402, Issue 6764
  • DOI: 10.1038/47282

The Large Nd3N@C2n (40≤n≤49) Cluster Fullerene Family: Preferential Templating of a C88 Cage by a Trimetallic Nitride Cluster
journal, December 2007

  • Melin, Frederic; Chaur, Manuel N.; Engmann, Sarah
  • Angewandte Chemie International Edition, Vol. 46, Issue 47
  • DOI: 10.1002/anie.200703489

New M3N@C2n Endohedral Metallofullerene Families (M=Nd, Pr, Ce;n=40–53): Expanding the Preferential Templating of the C88 Cage and Approaching the C96 Cage
journal, May 2008

  • Chaur, Manuel N.; Melin, Frederic; Elliott, Bevan
  • Chemistry - A European Journal, Vol. 14, Issue 15
  • DOI: 10.1002/chem.200800044

Lanthanum Nitride Endohedral Fullerenes La 3 N@C 2 n (43≤ n ≤55): Preferential Formation of La 3 N@C 96
journal, September 2008

  • Chaur, Manuel N.; Melin, Frederic; Ashby, Jarryd
  • Chemistry - A European Journal, Vol. 14, Issue 27
  • DOI: 10.1002/chem.200800881

Electronic Structure and Redox Properties of Metal Nitride Endohedral Fullerenes M 3 N@C 2 n (M=Sc, Y, La, and Gd; 2 n =80, 84, 88, 92, 96)
journal, September 2009

  • Valencia, Ramón; Rodríguez-Fortea, Antonio; Clotet, Anna
  • Chemistry - A European Journal, Vol. 15, Issue 41
  • DOI: 10.1002/chem.200900728

Different Extraction Behaviors between Divalent and Trivalent Endohedral Metallofullerenes
journal, March 2004

  • Lian, Yongfu; Shi, Zujin; Zhou, Xihuang
  • Chemistry of Materials, Vol. 16, Issue 9
  • DOI: 10.1021/cm0344156

Structural and electronic properties of endohedral metallofullerenes
journal, April 2012


Selective Extraction and Purification of Endohedral Metallofullerene from Carbon Soot
journal, November 2006

  • Tsuchiya, Takahiro; Wakahara, Takatsugu; Lian, Yongfu
  • The Journal of Physical Chemistry B, Vol. 110, Issue 45
  • DOI: 10.1021/jp0650679

Partial separation of fullerenes by gradient sublimation
journal, September 1993

  • Yeretzian, Chahan; Wiley, John B.; Holczer, Karoly
  • The Journal of Physical Chemistry, Vol. 97, Issue 39
  • DOI: 10.1021/j100141a033

Improved Production and Separation Processes for Gadolinium Metallofullerenes
journal, May 2008

  • Raebiger, James W.; Bolskar, Robert D.
  • The Journal of Physical Chemistry C, Vol. 112, Issue 17
  • DOI: 10.1021/jp076437b

Purification of Trimetallic Nitride Templated Endohedral Metallofullerenes by a Chemical Reaction of Congeners with Eutectic 9-Methylanthracene
journal, June 2008

  • Angeli, Clairette D.; Cai, Ting; Duchamp, James C.
  • Chemistry of Materials, Vol. 20, Issue 15
  • DOI: 10.1021/cm800795q

Rapid Removal of D 5 h Isomer Using the “Stir and Filter Approach” and Isolation of Large Quantities of Isomerically Pure Sc 3 N@C 80 Metallic Nitride Fullerenes
journal, May 2007

  • Stevenson, Steven; Mackey, Mary A.; Coumbe, Curtis E.
  • Journal of the American Chemical Society, Vol. 129, Issue 19
  • DOI: 10.1021/ja070795a

Nonchromatographic “Stir and Filter Approach” (SAFA) for Isolating Sc 3 N@C 80 Metallofullerenes
journal, July 2006

  • Stevenson, Steven; Harich, Kim; Yu, Hua
  • Journal of the American Chemical Society, Vol. 128, Issue 27
  • DOI: 10.1021/ja060752e

Selective Complexation and Reactivity of Metallic Nitride and Oxometallic Fullerenes with Lewis Acids and Use as an Effective Purification Method
journal, November 2009

  • Stevenson, Steven; Mackey, Mary A.; Pickens, Jane E.
  • Inorganic Chemistry, Vol. 48, Issue 24
  • DOI: 10.1021/ic9017147

A reinvestigation of the electrochemical behavior of Sc3N@C80
journal, March 2008

  • Plonska-Brzezinska, Marta E.; Athans, Andreas J.; Paige Phillips, J.
  • Journal of Electroanalytical Chemistry, Vol. 614, Issue 1-2
  • DOI: 10.1016/j.jelechem.2007.11.013

A Simple Isomeric Separation of D 5 h and I h Sc 3 N@C 80 by Selective Chemical Oxidation
journal, August 2005

  • Elliott, Bevan; Yu, Lei; Echegoyen, Luis
  • Journal of the American Chemical Society, Vol. 127, Issue 31
  • DOI: 10.1021/ja052446r

An Efficient Method to Separate Sc 3 N@C 80 I h and D 5 h Isomers and Sc 3 N@C 78 by Selective Oxidation with Acetylferrocenium [Fe(COCH 3 C 5 H 4 )Cp] +
journal, April 2013

  • Cerón, Maira R.; Li, Fang-Fang; Echegoyen, Luis
  • Chemistry - A European Journal, Vol. 19, Issue 23
  • DOI: 10.1002/chem.201204219

The stability of the fullerenes Cn, with n = 24, 28, 32, 36, 50, 60 and 70
journal, October 1987


Endohedral fullerenes: the importance of electronic, size and shape complementarity between the carbon cages and the corresponding encapsulated clusters: ENDOHEDRAL FULLERENES
journal, January 2014

  • Cerón, Maira R.; Li, Fang-Fang; Echegoyen, Luis A.
  • Journal of Physical Organic Chemistry, Vol. 27, Issue 4
  • DOI: 10.1002/poc.3245

Aromaticity as the driving force for the stability of non-IPR endohedral metallofullerene Bingel–Hirsch adducts
journal, January 2013

  • Garcia-Borràs, Marc; Osuna, Sílvia; Swart, Marcel
  • Chemical Communications, Vol. 49, Issue 78
  • DOI: 10.1039/c3cc44505d

Maximum Aromaticity as a Guiding Principle for the Most Suitable Hosting Cages in Endohedral Metallofullerenes
journal, July 2013

  • Garcia-Borràs, Marc; Osuna, Sílvia; Swart, Marcel
  • Angewandte Chemie International Edition, Vol. 52, Issue 35
  • DOI: 10.1002/anie.201303636

Reactivity differences of Sc 3 N@C 2n (2n = 68 and 80). Synthesis of the first methanofullerene derivatives of Sc 3 N@D 5h -C 80
journal, January 2016

  • Cerón, Maira R.; Izquierdo, Marta; Alegret, Núria
  • Chemical Communications, Vol. 52, Issue 1
  • DOI: 10.1039/C5CC07416A

Isolation and Structural Characterization of the Endohedral Fullerene Sc3N@C78
journal, April 2001


Sc3N@C68: Folded Pentalene Coordination in an Endohedral Fullerene that Does Not Obey the Isolated Pentagon Rule
journal, February 2003

  • Olmstead, Marilyn M.; Lee, Hon Man; Duchamp, James C.
  • Angewandte Chemie International Edition, Vol. 42, Issue 8
  • DOI: 10.1002/anie.200390237

Structure and Enhanced Reactivity Rates of the D 5 h Sc 3 N@C 80 and Lu 3 N@C 80 Metallofullerene Isomers:  The Importance of the Pyracylene Motif
journal, July 2006

  • Cai, Ting; Xu, Liaosa; Anderson, Mark R.
  • Journal of the American Chemical Society, Vol. 128, Issue 26
  • DOI: 10.1021/ja0615573

A single crystal X-ray diffraction study of a fully ordered cocrystal of pristine Sc3N@D3h(5)–C78
journal, July 2013


Recent progress in the chemistry of endohedral metallofullerenes
journal, January 2014

  • Lu, Xing; Bao, Lipiao; Akasaka, Takeshi
  • Chem. Commun., Vol. 50, Issue 94
  • DOI: 10.1039/C4CC05164E

Metal Sulfide in a C 82 Fullerene Cage: A New Form of Endohedral Clusterfullerenes
journal, April 2010

  • Dunsch, Lothar; Yang, Shangfeng; Zhang, Lin
  • Journal of the American Chemical Society, Vol. 132, Issue 15
  • DOI: 10.1021/ja909580j

Endohedral Clusterfullerenes: Future Perspectives
journal, January 2017

  • Cai, Wenting; Murillo, Jesse; Echegoyen, Luis
  • ECS Journal of Solid State Science and Technology, Vol. 6, Issue 6
  • DOI: 10.1149/2.0081706jss

Gd 3 N@C 2 n ( n = 40, 42, and 44):  Remarkably Low HOMO−LUMO Gap and Unusual Electrochemical Reversibility of Gd 3 N@C 88
journal, November 2007

  • Chaur, Manuel N.; Melin, Frederic; Elliott, Bevan
  • Journal of the American Chemical Society, Vol. 129, Issue 47
  • DOI: 10.1021/ja075930y

Is the Isolated Pentagon Rule Merely a Suggestion for Endohedral Fullerenes? The Structure of a Second Egg-Shaped Endohedral Fullerene—Gd 3 N@ C s (39663)-C 82
journal, June 2008

  • Mercado, Brandon Q.; Beavers, Christine M.; Olmstead, Marilyn M.
  • Journal of the American Chemical Society, Vol. 130, Issue 25
  • DOI: 10.1021/ja8032263

Large Metal Ions in a Relatively Small Fullerene Cage: The Structure of Gd 3 N@ C 2 (22010)-C 78 Departs from the Isolated Pentagon Rule
journal, July 2009

  • Beavers, Christine M.; Chaur, Manuel N.; Olmstead, Marilyn M.
  • Journal of the American Chemical Society, Vol. 131, Issue 32
  • DOI: 10.1021/ja903741r

Relevance of Thermal Effects in the Formation of Endohedral Metallofullerenes: The Case of Gd 3 N@ C s (39663)-C 82 and Other Related Systems
journal, January 2013

  • Mulet-Gas, Marc; Rodríguez-Fortea, Antonio; Echegoyen, Luis
  • Inorganic Chemistry, Vol. 52, Issue 4
  • DOI: 10.1021/ic302239e

Isolation and Crystallographic Characterization of Gd 3 N@ D 2 (35)-C 88 through Non-Chromatographic Methods
journal, September 2015


Pyramidalization of Gd3N inside a C80 cage. The synthesis and structure of Gd3N@C80
journal, January 2004

  • Stevenson, Steven; Phillips, J. Paige; Reid, Jon E.
  • Chemical Communications, Issue 24
  • DOI: 10.1039/b412338g

Synthesis of a new endohedral fullerene family, Sc2S@C2n (n = 40–50) by the introduction of SO2
journal, January 2010

  • Chen, Ning; Chaur, Manuel N.; Moore, Cheryl
  • Chemical Communications, Vol. 46, Issue 26
  • DOI: 10.1039/c0cc00835d

The Shape of the Sc 22 -S) Unit Trapped in C 82 : Crystallographic, Computational, and Electrochemical Studies of the Isomers, Sc 22 -S)@ C s (6)-C 82 and Sc 22 -S)@ C 3 v (8)-C 82
journal, May 2011

  • Mercado, Brandon Q.; Chen, Ning; Rodríguez-Fortea, Antonio
  • Journal of the American Chemical Society, Vol. 133, Issue 17
  • DOI: 10.1021/ja200289w

La@C 72 Having a Non-IPR Carbon Cage
journal, November 2006

  • Wakahara, Takatsugu; Nikawa, Hidefumi; Kikuchi, Takashi
  • Journal of the American Chemical Society, Vol. 128, Issue 44
  • DOI: 10.1021/ja064751y

Disclosure of the Elusive C 2 v -C 72 Carbon Cage
journal, December 2010

  • Ziegler, Karolin; Mueller, Andreas; Amsharov, Konstantin Yu.
  • Journal of the American Chemical Society, Vol. 132, Issue 48
  • DOI: 10.1021/ja108470p

C 72 Cl 4 : A Pristine Fullerene with Favorable Pentagon-Adjacent Structure
journal, December 2010

  • Tan, Yuan-Zhi; Zhou, Ting; Bao, Jian
  • Journal of the American Chemical Society, Vol. 132, Issue 48
  • DOI: 10.1021/ja108860y

Chemical Understanding of a Non-IPR Metallofullerene: Stabilization of Encaged Metals on Fused-Pentagon Bonds in La 2 @C 72
journal, June 2008

  • Lu, Xing; Nikawa, Hidefumi; Nakahodo, Tsukasa
  • Journal of the American Chemical Society, Vol. 130, Issue 28
  • DOI: 10.1021/ja8019577

Sc 2 S@ C s (10528)-C 72 : A Dimetallic Sulfide Endohedral Fullerene with a Non Isolated Pentagon Rule Cage
journal, April 2012

  • Chen, Ning; Beavers, Christine M.; Mulet-Gas, Marc
  • Journal of the American Chemical Society, Vol. 134, Issue 18
  • DOI: 10.1021/ja300765z

Sc 2 S@C 2 (7892)–C 70 : a metallic sulfide cluster inside a non-IPR C 70 cage
journal, January 2013

  • Chen, Ning; Mulet-Gas, Marc; Li, Yu-Yang
  • Chem. Sci., Vol. 4, Issue 1
  • DOI: 10.1039/C2SC21101G

Which Do Endohedral Ti 2 C 80 Metallofullerenes Prefer Energetically:  Ti 2 @C 80 or Ti 2 C 2 @C 78 ? A Theoretical Study
journal, November 2005

  • Yumura, Takashi; Sato, Yuta; Suenaga, Kazutomo
  • The Journal of Physical Chemistry B, Vol. 109, Issue 43
  • DOI: 10.1021/jp0519767

Ti2C80 is more likely a titanium carbide endohedral metallofullerene (Ti2C2)@C78
journal, January 2005


Direct imaging of intracage structure in titanium-carbide endohedral metallofullerene
journal, May 2006


Production, Isolation, and EELS Characterization of Ti 2 @C 84 Dititanium Metallofullerenes
journal, September 2002

  • Cao, Baopeng; Suenaga, Kazutomo; Okazaki, Toshiya
  • The Journal of Physical Chemistry B, Vol. 106, Issue 36
  • DOI: 10.1021/jp026013b

An endohedral titanium(iii) in a clusterfullerene: putting a non-group-III metal nitride into the C80-Ih fullerene cage
journal, January 2009

  • Yang, Shangfeng; Chen, Chuanbao; Popov, Alexey A.
  • Chemical Communications, Issue 42
  • DOI: 10.1039/b911267g

Ti2S@D3h(24109)-C78: a sulfide cluster metallofullerene containing only transition metals inside the cage
journal, January 2013

  • Li, Fang-Fang; Chen, Ning; Mulet-Gas, Marc
  • Chemical Science, Vol. 4, Issue 9
  • DOI: 10.1039/c3sc51124c

A Scandium Carbide Endohedral Metallofullerene: (Sc2C2)@C84
journal, January 2001


Clusters Encapsulated in Endohedral Metallofullerenes: How Strained Are They?
journal, March 2014

  • Deng, Qingming; Popov, Alexey A.
  • Journal of the American Chemical Society, Vol. 136, Issue 11
  • DOI: 10.1021/ja4122582

A Bent Tb 2 C 2 Cluster Encaged in a C S (6)-C 82 Cage: Synthesis, Isolation and X-ray Crystallographic Study
journal, January 2014


Beyond the Butterfly: Sc 2 C 2 @ C 2 v (9)-C 86 , an Endohedral Fullerene Containing a Planar, Twisted Sc 2 C 2 Unit with Remarkable Crystalline Order in an Unprecedented Carbon Cage
journal, August 2015

  • Chen, Chia-Hsiang; Ghiassi, Kamran B.; Cerón, Maira R.
  • Journal of the American Chemical Society, Vol. 137, Issue 32
  • DOI: 10.1021/jacs.5b06425

Zigzag Sc 2 C 2 Carbide Cluster inside a [88]Fullerene Cage with One Heptagon, Sc 2 C 2 @ C s (hept)-C 88 : A Kinetically Trapped Fullerene Formed by C 2 Insertion?
journal, September 2016

  • Chen, Chia-Hsiang; Abella, Laura; Cerón, Maira R.
  • Journal of the American Chemical Society, Vol. 138, Issue 39
  • DOI: 10.1021/jacs.6b07912

Bottom-up formation of endohedral mono-metallofullerenes is directed by charge transfer
journal, December 2014

  • Dunk, Paul W.; Mulet-Gas, Marc; Nakanishi, Yusuke
  • Nature Communications, Vol. 5, Issue 1
  • DOI: 10.1038/ncomms6844

The First Fulleropyrrolidine Derivative of Sc 3 N@C 80 :  Pronounced Chemical Shift Differences of the Geminal Protons on the Pyrrolidine Ring
journal, June 2005

  • Cardona, Claudia M.; Kitaygorodskiy, Alex; Ortiz, Angy
  • The Journal of Organic Chemistry, Vol. 70, Issue 13
  • DOI: 10.1021/jo0503456

Trimetallic Nitride Endohedral Fullerenes: Experimental and Theoretical Evidence for the M 3 N 6+ @C 2 n 6− model
journal, February 2009

  • Chaur, Manuel N.; Valencia, Ramón; Rodríguez‐Fortea, Antonio
  • Angewandte Chemie International Edition, Vol. 48, Issue 8
  • DOI: 10.1002/anie.200802777

Trimetallic Nitride Endohedral Metallofullerenes:  Reactivity Dictated by the Encapsulated Metal Cluster
journal, July 2005

  • Cardona, Claudia M.; Kitaygorodskiy, Alex; Echegoyen, Luis
  • Journal of the American Chemical Society, Vol. 127, Issue 29
  • DOI: 10.1021/ja052153y

X-Ray crystallographic and EPR spectroscopic characterization of a pyrrolidine adduct of Y3N@C80
journal, January 2006

  • Echegoyen, Luis; Chancellor, Christopher J.; Cardona, Claudia M.
  • Chemical Communications, Issue 25
  • DOI: 10.1039/b604011j

Dancing on a Fullerene Surface: Isomerization of Y3N@(N-Ethylpyrrolidino-C80) from the 6,6 to the 5,6 Regioisomer
journal, December 2006

  • Rodríguez-Fortea, Antonio; Campanera, Josep M.; Cardona, Claudia M.
  • Angewandte Chemie International Edition, Vol. 45, Issue 48
  • DOI: 10.1002/anie.200604052

Prato Reaction of M 3 N@ I h -C 80 (M = Sc, Lu, Y, Gd) with Reversible Isomerization
journal, December 2012

  • Aroua, Safwan; Yamakoshi, Yoko
  • Journal of the American Chemical Society, Vol. 134, Issue 50
  • DOI: 10.1021/ja309550z

Retro-Cycloaddition Reaction of Pyrrolidinofullerenes
journal, January 2006

  • Martín, Nazario; Altable, Margarita; Filippone, Salvatore
  • Angewandte Chemie International Edition, Vol. 45, Issue 1
  • DOI: 10.1002/anie.200502556

“Open Rather than Closed” Malonate Methano-Fullerene Derivatives. The Formation of Methanofulleroid Adducts of Y 3 N@C 80
journal, August 2007

  • Lukoyanova, Olena; Cardona, Claudia M.; Rivera, José
  • Journal of the American Chemical Society, Vol. 129, Issue 34
  • DOI: 10.1021/ja071733n

Bingel−Hirsch Reactions on Non-IPR Gd 3 N@C 2 n (2 n = 82 and 84)
journal, December 2010

  • Alegret, Núria; Chaur, Manuel N.; Santos, Eva
  • The Journal of Organic Chemistry, Vol. 75, Issue 23
  • DOI: 10.1021/jo101620b

Synthesis and Electrochemical Studies of Bingel-Hirsch Derivatives of M3N@Ih-C80 (M=Sc, Lu)
journal, March 2010

  • Pinzón, Julio R.; Zuo, Tianming; Echegoyen, Luis
  • Chemistry - A European Journal, Vol. 16, Issue 16
  • DOI: 10.1002/chem.200903155

The Regioselectivity of Bingel-Hirsch Cycloadditions on Isolated Pentagon Rule Endohedral Metallofullerenes
journal, January 2016

  • Garcia-Borràs, Marc; Cerón, Maira R.; Osuna, Sílvia
  • Angewandte Chemie International Edition, Vol. 55, Issue 7
  • DOI: 10.1002/anie.201509057

The influence of cage size on the reactivity of trimetallic nitride metallofullerenes: a mono- and bis-methanoadduct of Gd3N@C80 and a monoadduct of Gd3N@C84
journal, January 2008

  • Chaur, Manuel N.; Melin, Frederic; Athans, Andreas J.
  • Chemical Communications, Issue 23
  • DOI: 10.1039/b804847a

Buckyball maracas: exploring the inside and outside properties of endohedral fullerenes: BUCKYBALL MARACAS: ENDOHEDRAL FULLERENES
journal, August 2012

  • Rivera-Nazario, Danisha M.; Pinzón, Julio R.; Stevenson, Steven
  • Journal of Physical Organic Chemistry, Vol. 26, Issue 2
  • DOI: 10.1002/poc.3009

Reactivity of Metallic Nitride Endohedral Metallofullerene Anions: Electrochemical Synthesis of a Lu 3 N@ I h -C 80 Derivative
journal, March 2011

  • Li, Fang-Fang; Rodríguez-Fortea, Antonio; Poblet, Josep M.
  • Journal of the American Chemical Society, Vol. 133, Issue 8
  • DOI: 10.1021/ja110160j

Electrosynthesis of a Sc 3 N@ I h -C 80 Methano Derivative from Trianionic Sc 3 N@ I h -C 80
journal, April 2012

  • Li, Fang-Fang; Rodríguez-Fortea, Antonio; Peng, Ping
  • Journal of the American Chemical Society, Vol. 134, Issue 17
  • DOI: 10.1021/ja3008038

Endohedral fullerenes for organic photovoltaic devices
journal, February 2009

  • Ross, Russel B.; Cardona, Claudia M.; Guldi, Dirk M.
  • Nature Materials, Vol. 8, Issue 3
  • DOI: 10.1038/nmat2379

Diphenylmethanofullerenes: New and Efficient Acceptors in Bulk-Heterojunction Solar Cells
journal, December 2005

  • Riedel, I.; von Hauff, E.; Parisi, J.
  • Advanced Functional Materials, Vol. 15, Issue 12
  • DOI: 10.1002/adfm.200500097

The Origin of the High Voltage in DPM12/P3HT Organic Solar Cells
journal, July 2010

  • Sánchez-Díaz, Antonio; Izquierdo, Marta; Filippone, Salvatore
  • Advanced Functional Materials, Vol. 20, Issue 16
  • DOI: 10.1002/adfm.201000549

Polymer solar cells based on diphenylmethanofullerenes with reduced sidechain length
journal, January 2011

  • Bolink, Henk J.; Coronado, Eugenio; Forment-Aliaga, Alicia
  • J. Mater. Chem., Vol. 21, Issue 5
  • DOI: 10.1039/C0JM01160F

Origin of the Open Circuit Voltage of Plastic Solar Cells
journal, October 2001


[5,6]-Open Methanofullerene Derivatives of I h -C 80
journal, September 2013

  • Izquierdo, Marta; Cerón, Maira R.; Olmstead, Marilyn M.
  • Angewandte Chemie International Edition, Vol. 52, Issue 45
  • DOI: 10.1002/anie.201305476

Sc3N@C80-Ferrocene Electron-Donor/Acceptor Conjugates as Promising Materials for Photovoltaic Applications
journal, May 2008

  • Pinzón, Julio R.; Plonska-Brzezinska, Marta E.; Cardona, Claudia M.
  • Angewandte Chemie International Edition, Vol. 47, Issue 22
  • DOI: 10.1002/anie.200800473

Complexation of Sc 3 N@C 80 Endohedral Fullerene with Cyclic Zn-Bisporphyrins: Solid State and Solution Studies
journal, May 2011

  • Hernández-Eguía, Laura P.; Escudero-Adán, Eduardo C.; Pinzón, Julio R.
  • The Journal of Organic Chemistry, Vol. 76, Issue 9
  • DOI: 10.1021/jo200154d

Syntheses and Structures of Phenyl-C 81 -Butyric Acid Methyl Esters (PCBMs) from M 3 N@C 80
journal, March 2009

  • Shu, Chunying; Xu, Wei; Slebodnick, Carla
  • Organic Letters, Vol. 11, Issue 8
  • DOI: 10.1021/ol9002527

Endohedral Metallofullerenes-Filled Fullerene Derivatives towards Multifunctional Reaction Center Mimics
journal, March 2012

  • Rudolf, Marc; Wolfrum, Silke; Guldi, Dirk M.
  • Chemistry - A European Journal, Vol. 18, Issue 17
  • DOI: 10.1002/chem.201102844

Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M 3 N@ I h -C 80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control
journal, September 2015

  • Cerón, Maira R.; Izquierdo, Marta; Garcia-Borràs, Marc
  • Journal of the American Chemical Society, Vol. 137, Issue 36
  • DOI: 10.1021/jacs.5b07207

Endohedral Metal-Induced Regioselective Formation of Bis-Prato Adduct of Y 3 N@ I h -C 80 and Gd 3 N@ I h -C 80
journal, December 2014

  • Aroua, Safwan; Garcia-Borràs, Marc; Bölter, Marc Florian
  • Journal of the American Chemical Society, Vol. 137, Issue 1
  • DOI: 10.1021/ja511008z

Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology
journal, February 2012

  • Mishra, Amaresh; Bäuerle, Peter
  • Angewandte Chemie International Edition, Vol. 51, Issue 9
  • DOI: 10.1002/anie.201102326

Tethered Bisadducts of C 60 and C 70 with Addends on a Common Hexagonal Face and a 12-Membered Hole in the Fullerene Cage
journal, June 2015

  • Cerón, Maira R.; Izquierdo, Marta; Aghabali, Amineh
  • Journal of the American Chemical Society, Vol. 137, Issue 23
  • DOI: 10.1021/jacs.5b03768

Tether-Directed Bisfunctionalization Reactions of C 60 and C 70
journal, April 2015

  • Cerón, Maira R.; Izquierdo, Marta; Pi, Yunhong
  • Chemistry - A European Journal, Vol. 21, Issue 21
  • DOI: 10.1002/chem.201500206

Unexpected Isomerism in cis -2 Bis(pyrrolidino)[60]Fullerene Diastereomers
journal, October 2013

  • Izquierdo, Marta; Cerón, Maira R.; Alegret, Núria
  • Angewandte Chemie International Edition, Vol. 52, Issue 49
  • DOI: 10.1002/anie.201306957

Chemical, Electrochemical, and Structural Properties of Endohedral Metallofullerenes
journal, September 2009

  • Chaur, Manuel N.; Melin, Frederic; Ortiz, Angy L.
  • Angewandte Chemie International Edition, Vol. 48, Issue 41
  • DOI: 10.1002/anie.200901746

Effect of Water and Solvent Selection on the SAFA Purification Times for Metallic Nitride Fullerenes
journal, January 2014

  • Stevenson, Steven; Rose, Coralie B.; Robson, Alyssa A.
  • Fullerenes, Nanotubes and Carbon Nanostructures, Vol. 22, Issue 1-3
  • DOI: 10.1080/1536383X.2013.798725

Works referencing / citing this record:

All‐Fullerene Electron Donor–Acceptor Conjugates
journal, March 2019

  • Izquierdo, Marta; Platzer, Benedikt; Stasyuk, Anton J.
  • Angewandte Chemie, Vol. 131, Issue 21
  • DOI: 10.1002/ange.201901863

All‐Fullerene Electron Donor–Acceptor Conjugates
journal, May 2019

  • Izquierdo, Marta; Platzer, Benedikt; Stasyuk, Anton J.
  • Angewandte Chemie International Edition, Vol. 58, Issue 21
  • DOI: 10.1002/anie.201901863

Nitrogen centered inverse coordination complexes. A survey of molecular topologies
journal, October 2018


Far infrared spectroscopy and other spectral and thermal properties of [Li@C 60 ]PF 6
journal, June 2019

  • Cataldo, Franco; García-Hernández, D. Aníbal; Manchado, Arturo
  • Fullerenes, Nanotubes and Carbon Nanostructures, Vol. 27, Issue 9
  • DOI: 10.1080/1536383x.2019.1633521