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Construction of Giant Dendrimers Using a Tripodal Building Block

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Contribution from the Laboratoire de Chimie Organique et Organométallique, UMR CNRS No. 5802, Laboratoire de Physico-Chimie Moléculaire, UMR CNRS 5803, Laboratoire de Chimie des Polymères Organiques, UMR CNRS 5629, Université Bordeaux I, 33405 Talence Cedex, France, and Laboratoire de Chimie Structurale Organique et Biologique, UMR CNRS No. 7613, Université Paris VI, 4 Place Jussieu, 75252 Paris, France
Cite this: J. Am. Chem. Soc. 2003, 125, 24, 7250–7257
Publication Date (Web):May 21, 2003
https://doi.org/10.1021/ja021147o
Copyright © 2003 American Chemical Society
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    Abstract

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    Giant pentane-soluble organo-silicon dendrimers have been synthesized using a triallylphenol brick according to a new divergent construction that uses a hydrosilylation−nucleophilic substitution sequence up to the ninth generation (G9). All the reactions were monitored by 1H, 13C, and 29Si NMR until G9, indicating that they were clean at the NMR accuracy until this last generation. MALDI TOF mass spectra were recorded for G1 to G4 and show the nature and amounts of defects that are intrinsic to the divergent construction. This technique and SEC (recorded up to G5) confirm the monodispersity (1.00 to 1.02) from G1 to G5. HRTEM and AFM images recorded for the high generations disclose the expected smooth dendrimer size progression and the globular shape. At G9, the theoretical number of termini (TNT) is 177 407 branches (abbreviation:  G9-177 047). It is estimated that more than 105 terminal branches are actually present in the G9 dendrimer, far beyond the De Gennes “dense-packing” limit (6000 branches), and it is believed that the branch termini turn inside the dendrimer toward the core. This is corroborated by lower reaction rates and yields for the highest generation numbers presumably due to intradendritic reactions. It is probable that the dendritic construction is limited by the density of branches inside the dendrimer, i.e., far beyond the dense-packing limit.

    †

     LCOO, Université Bordeaux I.

    ‡

     LPCM, Université Bordeaux I.

    §

     LPCO, Université Bordeaux I.

    ⊥

     LCSOB, Université Paris VI.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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    400 MHz 1H, 100.6 MHz 13C, and 59.6 MHz 29Si NMR spectra for all generations (G1 to G9) of dendrimers, G0-SiCH2OH and 1H NMR spectrum of a mixture of G2-81-allyl and G0-SiCH2OH, and MALDI TOF mass spectrum of G1-27-allyl. This material is available free of charge via the Internet at http://pubs.acs.org.

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    79. Didier Astruc, Jaime Ruiz. Organoiron-mediated dendrimer syntheses with 1→3 connectivity and applications. Tetrahedron 2010, 66 (10) , 1769-1785. https://doi.org/10.1016/j.tet.2009.11.116
    80. Didier Astruc, Cátia Ornelas, Jaime Ruiz. Dendritic Molecular Electrochromic Batteries Based on Redox‐Robust Metallocenes. Chemistry – A European Journal 2009, 15 (36) , 8936-8944. https://doi.org/10.1002/chem.200901294
    81. Jérémy Camponovo, Jaime Ruiz, Eric Cloutet, Didier Astruc. New Polyalkynyl Dendrons and Dendrimers: “Click” Chemistry with Azidomethylferrocene and Specific Anion and Cation Electrochemical Sensing Properties of the 1,2,3‐Triazole‐Containing Dendrimers. Chemistry – A European Journal 2009, 15 (12) , 2990-3002. https://doi.org/10.1002/chem.200801999
    82. Elodie Boisselier, Anita Chan Kam Shun, Jaime Ruiz, Eric Cloutet, Colette Belin, Didier Astruc. Ferrocenyl dendronized polymers. New Journal of Chemistry 2009, 33 (2) , 246. https://doi.org/10.1039/b819604d
    83. Didier Astruc. Electron-reservoir complexes and other redox-robust reagents: functions and applications. New Journal of Chemistry 2009, 33 (6) , 1191. https://doi.org/10.1039/b903188j
    84. Elodie Boisselier, Cátia Ornelas, Isabelle Pianet, Jaime Ruiz Aranzaes, Didier Astruc. Four Generations of Water-Soluble Dendrimers with 9 to 243 Benzoate Tethers: Synthesis and Dendritic Effects on Their Ion Pairing with Acetylcholine, Benzyltriethylammonium, and Dopamine in Water. Chemistry - A European Journal 2008, 14 (18) , 5577-5587. https://doi.org/10.1002/chem.200701607
    85. Sylvain Nlate, Lauriane Plault, François-Xavier Felpin, Didier Astruc. Fast and Scalable Route to Aryl Polyallyl Dendrons and Dendrimers. Advanced Synthesis & Catalysis 2008, 350 (9) , 1419-1424. https://doi.org/10.1002/adsc.200800163
    86. Iván Dorado, Román Andrés, Ernesto de Jesús, Juan Carlos Flores. Palladium(II) complexes of phosphane ligands with ammonium-functionalized carbosilane substituents. Journal of Organometallic Chemistry 2008, 693 (12) , 2147-2152. https://doi.org/10.1016/j.jorganchem.2008.03.015
    87. Cátia Ornelas, Jaime Ruiz, Lionel Salmon, Didier Astruc. Sulphonated “Click” Dendrimer-Stabilized Palladium Nanoparticles as Highly Efficient Catalysts for Olefin Hydrogenation and Suzuki Coupling Reactions Under Ambient Conditions in Aqueous Media. Advanced Synthesis & Catalysis 2008, 350 (6) , 837-845. https://doi.org/10.1002/adsc.200700584
    88. Alexander Trujillo, Sourisak Sinbandhit, Loïc Toupet, David Carrillo, Carolina Manzur, Jean-René Hamon. Organometallic–Inorganic Conjugated Unsymmetrical Schiff-Base Hybrids. Synthesis, Characterization, Electrochemistry and X-ray Crystal Structures of Functionalized Trinuclear Iron–Nickel–Ruthenium Dipolar Chromophores. Journal of Inorganic and Organometallic Polymers and Materials 2008, 18 (1) , 81-99. https://doi.org/10.1007/s10904-007-9181-9
    89. Didier Astruc, Catia Ornelas, Jaime Ruiz Aranzaes. Ferrocenyl-terminated Dendrimers: Design for Applications in Molecular Electronics, Molecular Recognition and Catalysis. Journal of Inorganic and Organometallic Polymers and Materials 2008, 18 (1) , 4-17. https://doi.org/10.1007/s10904-007-9191-7
    90. Cátia Ornelas, Jaime Ruiz Aranzaes, Lionel Salmon, Didier Astruc. “Click” Dendrimers: Synthesis, Redox Sensing of Pd(OAc) 2 , and Remarkable Catalytic Hydrogenation Activity of Precise Pd Nanoparticles Stabilized by 1,2,3-Triazole-Containing Dendrimers. Chemistry - A European Journal 2008, 14 (1) , 50-64. https://doi.org/10.1002/chem.200701410
    91. Jaime Ruiz Aranzaes, Didier Astruc. Simple synthesis of organo-iron complexes from iron-sandwich raw materials using visible light. Inorganica Chimica Acta 2008, 361 (1) , 1-4. https://doi.org/10.1016/j.ica.2007.07.030
    92. Jonathan V. M. Weaver, Richard T. Williams, Brodyck J. L. Royles, Paul H. Findlay, Andrew I. Cooper, Steven P. Rannard. pH-Responsive branched polymer nanoparticles. Soft Matter 2008, 4 (5) , 985. https://doi.org/10.1039/b718118c
    93. Elodie Boisselier, Abdou K. Diallo, Lionel Salmon, Jaime Ruiz, Didier Astruc. Gold nanoparticles synthesis and stabilization via new “clicked” polyethyleneglycol dendrimers. Chemical Communications 2008, 120 (39) , 4819. https://doi.org/10.1039/b808987f
    94. N. Jayaraman. Dendrimers and Their Use as Nanoscale Sensors. 2007, 249-297. https://doi.org/10.1002/9783527611362.ch8
    95. Cátia Ornelas, Jaime Ruiz Aranzaes, Eric Cloutet, Sandra Alves, Didier Astruc. Click Assembly of 1,2,3-Triazole-Linked Dendrimers, Including Ferrocenyl Dendrimers, Which Sense Both Oxo Anions and Metal Cations. Angewandte Chemie 2007, 119 (6) , 890-895. https://doi.org/10.1002/ange.200602858
    96. Cátia Ornelas, Jaime Ruiz Aranzaes, Eric Cloutet, Sandra Alves, Didier Astruc. Click Assembly of 1,2,3-Triazole-Linked Dendrimers, Including Ferrocenyl Dendrimers, Which Sense Both Oxo Anions and Metal Cations. Angewandte Chemie International Edition 2007, 46 (6) , 872-877. https://doi.org/10.1002/anie.200602858
    97. Cátia Ornelas, Elodie Boisselier, Victor Martinez, Isabelle Pianet, Jaime Ruiz Aranzaes, Didier Astruc. New water-soluble polyanionic dendrimers and binding to acetylcholine in water by means of contact ion-pairing interactions. Chemical Communications 2007, 18 (47) , 5093. https://doi.org/10.1039/b710391c
    98. Govindasamy Jayamurugan, Narayanaswamy Jayaraman. Synthesis of large generation poly(propyl ether imine) (PETIM) dendrimers. Tetrahedron 2006, 62 (41) , 9582-9588. https://doi.org/10.1016/j.tet.2006.07.094
    99. Denise Méry, Didier Astruc. Dendritic catalysis: Major concepts and recent progress. Coordination Chemistry Reviews 2006, 250 (15-16) , 1965-1979. https://doi.org/10.1016/j.ccr.2005.11.012
    100. Jaime Ruiz Aranzaes, Colette Belin, Didier Astruc. Assembly of Dendrimers with Redox-Active [{CpFe(μ3-CO)}4] Clusters at the Periphery and Their Application to Oxo-Anion and Adenosine-5′-Triphosphate Sensing. Angewandte Chemie 2006, 118 (1) , 138-142. https://doi.org/10.1002/ange.200502291
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