Synthesis and Properties of Fullerene-Rich Dendrimers

Owing to their peculiar electronic properties, fullerene derivatives are attractive building blocks for dendrimer chemistry. Whereas, for the main part, the fullerene-containing dendrimers reported so far have been prepared with a C60 core, dendritic structures with fullerene units at their surface or with C60 spheres in the dendritic branches have been more scarcely considered. This is mainly associated with the difficulties related to the synthesis of fullerene-rich molecules. In this review, the most recent developments on the molecular engineering of fullerene-rich dendrons and dendrimers are presented to illustrate the current state-of-the-art of fullerene chemistry for the preparation of new dendritic materials.

[1]  F. Vögtle,et al.  Fullerene-rich dendrimers: divergent synthesis and photophysical properties , 2009 .

[2]  C. Hawker,et al.  A new convergent approach to monodisperse dendritic macromolecules , 1990 .

[3]  C. Hawker,et al.  Fullerene-bound dendrimers. Soluble, isolated carbon clusters , 1993 .

[4]  A. Albrecht-Gary,et al.  Supramolecular click chemistry for the self-assembly of a stable Zn(II)-porphyrin-C60 conjugate. , 2005, Chemical communications.

[5]  J. Nierengarten,et al.  Molecular and supramolecular C60-oligophenylenevinylene conjugates. , 2007, Chemical communications.

[6]  F. Diederich,et al.  A new pyridyl-substituted methanofullerene derivative. Photophysics, electrochemistry and self-assembly with zinc(II) meso-tetraphenylporphyrin (ZnTPP) , 1999 .

[7]  A. Hirsch,et al.  Dendrimers with Carbon Rich-Cores , 2001 .

[8]  N. Armaroli,et al.  Fullerodendrimers with peripheral triethyleneglycol chains: synthesis, mass spectrometric characterization, and photophysical properties , 2002 .

[9]  P. Ceroni,et al.  Photoinduced energy transfer in a fullerene–oligophenylenevinylene conjugate , 2000 .

[10]  F. Vögtle,et al.  Dendrimers and Dendrons: Concepts, Syntheses, Applications , 2001 .

[11]  Regioselective intramolecular Pauson-Khand reactions of C60: an electrochemical study and theoretical underpinning. , 2005, Chemistry.

[12]  O. Ito,et al.  Photochemical and Photophysical Properties of C60 Dendrimers Studied by Laser Flash Photolysis , 2002 .

[13]  J. Nierengarten Chemical modification of C60 for materials science applications , 2004 .

[14]  J. Nierengarten Dendritic encapsulation of active core molecules , 2003 .

[15]  A. Hirsch,et al.  Efficient cyclopropanation of C60 starting from malonates , 1997 .

[16]  H. Imahori,et al.  Synthesis of Dendritic Branches with Peripheral Fullerene Subunits , 2006 .

[17]  M. El-Khouly,et al.  Silicon-phthalocyanine-cored fullerene dendrimers: synthesis and prolonged charge-separated states with dendrimer generations. , 2007, Chemistry.

[18]  S. Hotchandani,et al.  Electrodeposition of C60 Cluster Aggregates on Nanostructured SnO2 Films for Enhanced Photocurrent Generation , 2000 .

[19]  C. Amatore,et al.  Synthesis and electrochemical properties of fullerene-rich nanoclusters synthesized by cobalt-catalyzed cyclotrimerization of bis(aryl)alkyne fullerodendrimers. , 2007, Angewandte Chemie.

[20]  J. Nierengarten Fullerodendrimers: fullerene-containing macromolecules with intriguing properties. , 2003, Topics in current chemistry.

[21]  J. Nicoud,et al.  Methanofullerene-functionalized dendritic branches , 2000 .

[22]  Nierengarten Fullerodendrimers: a new class of compounds for supramolecular chemistry and materials science applications , 2000, Chemistry.

[23]  N. Armaroli,et al.  [60]Fullerene: a versatile photoactive core for dendrimer chemistry. , 2003, Chemistry.

[24]  C. Burger,et al.  Spherical bilayer vesicles of fullerene-based surfactants in water: a laser light scattering study. , 2001, Science.

[25]  M. Zandler,et al.  Studies on Covalently Linked Porphyrin−C60 Dyads: Stabilization of Charge-Separated States by Axial Coordination , 2002 .

[26]  P. Masson,et al.  Polarity effects on the photophysics of dendrimers with an oligophenylenevinylene core and peripheral fullerene units. , 2004, Chemistry.

[27]  N. Schore Transition metal-mediated cycloaddition reactions of alkynes in organic synthesis , 1988 .

[28]  C. Duhayon,et al.  Self-assembly of fullerene-rich nanostructures with a stannoxane core. , 2007, Chemical communications.

[29]  M. Delville,et al.  One-, two- and three-electron reduction of C60 using the electron-reservoir complex [FeI(C5H5)(C6Me6)] , 1993 .

[30]  J. Nicoud,et al.  Phenanthroline ligands substituted with fullerene-functionalized dendritic wedges and their copper(I) complexes , 1999 .

[31]  J. F. Stoddart,et al.  Stable Langmuir and Langmuir-Blodgett films of fullerene-glycodendron conjugates , 1998 .

[32]  J. Nicoud,et al.  PREPARATION OF DENDRONS WITH PERIPHERAL FULLERENE UNITS , 1999 .

[33]  Guillon,et al.  Investigations of Thin Films with Amphiphilic Dendrimers Bearing Peripheral Fullerene Subunits. , 2000, Angewandte Chemie.

[34]  T. Aida,et al.  Construction of segregated arrays of multiple donor and acceptor units using a dendritic scaffold: remarkable dendrimer effects on photoinduced charge separation. , 2006, Journal of the American Chemical Society.

[35]  H. Imahori,et al.  Dendritic Effects on Structure and Photophysical and Photoelectrochemical Properties of Fullerene Dendrimers and Their Nanoclusters , 2007 .

[36]  G. Koten,et al.  An octa-cationic core-shell dendrimer as a molecular template for the assembly of anionic fullerene derivatives , 2005 .

[37]  D. Guillon,et al.  Amphiphilic diblock dendrimers: synthesis and incorporation in Langmuir and Langmuir-Blodgett films. , 2001, Journal of the American Chemical Society.

[38]  J. Nierengarten,et al.  Supramolecular chemistry for the self-assembly of fullerene-rich dendrimers , 2007 .