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Dendrimers: Towards Catalytic, Material and Biomedical Uses

ISBN: 978-1-119-97757-5
456 pages
August 2011
Dendrimers: Towards Catalytic, Material and Biomedical Uses (1119977576) cover image
This book will be mainly focussed on the properties and uses of dendrimers and dendrons. The aim of this book is to be the reference book about dendrimers applications. It will not describe all details, but it will give the reader a unique overview of what has currently been done with dendrimers, with numerous references and illustrations. It will be divided in four main parts: Part 1) Generalities, syntheses, characterizations and properties; Part 2) Applications in catalysis; Part 3) Applications for the elaboration or modification of materials; and Part 4) Applications in biology/medicine. The role of the nanometric size and the multiple functions of dendrimers on the properties will be emphasized.
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Preface xv

Part 1 Generalities, Syntheses, Characterizations, and Physicochemical Properties 1

1 Syntheses of Dendrimers and Dendrons 3
Anne-Marie Caminade

1.1 Introduction: What Are Dendrimers and Dendrons? 3

1.2 Syntheses of Poly(propyleneimine) Dendrimers (PPI) 5

1.3 Synthesis of Poly(amidoamine) Dendrimers (PAMAM) 5

1.4 Syntheses of Poly(ether) Dendrimers 7

1.5 Syntheses of Poly(ester) Dendrimers 10

1.6 Synthesis of Poly(lysine) Dendrimers 14

1.7 Syntheses of Silicon-Containing Dendrimers 15

1.8 Syntheses of Phosphorus-Containing Dendrimers 16

1.9 Syntheses of Carbon-Based Dendrimers 17

1.10 Syntheses of Dendrimers Constituted of Nitrogen Heterocycles 19

1.11 Syntheses by Self-Assembly 21

1.12 Accelerated Syntheses 26

1.13 Conclusion 30

References 30

2 Methods of Characterization of Dendrimers 35
Anne-Marie Caminade

2.1 Introduction 35

2.2 Spectroscopy and Spectrometry 36

2.2.1 Nuclear Magnetic Resonance (NMR) 36

2.2.2 Mass Spectrometry 40

2.2.3 X-ray Diffraction 41

2.2.4 Infrared (IR) and Raman Spectroscopy 42

2.2.5 Ultraviolet–Visible (UV–vis) Spectroscopy 43

2.2.6 Fluorescence 44

2.2.7 Chirality, Optical Rotation, and Circular Dichroism (CD) 45

2.2.8 Electron Paramagnetic Resonance (EPR) 45

2.2.9 Electrochemistry 46

2.2.10 Magnetometry 46

2.2.11 Mössbauer Spectroscopy 46

2.2.12 X-ray Spectroscopies 47

2.3 Scattering Techniques 47

2.3.1 Laser Light Scattering (LLS) 47

2.3.2 Small-Angle Neutron Scattering (SANS) 47

2.3.3 Small-Angle X-ray Scattering (SAXS) and

Wide-Angle X-ray Scattering (WAXS) 48

2.4 Microscopy 48

2.4.1 Transmission Electron Microscopy (TEM) 49

2.4.2 Atomic Force Microscopy (AFM) 49

2.4.3 Polarizing Optical Microscopy (POM) 50

2.5 Rheology and Physical Characterizations 50

2.5.1 Intrinsic Viscosity 50

2.5.2 Differential Scanning Calorimetry (DSC) 50

2.5.3 Dielectric Spectroscopy (DS) 51

2.5.4 Dipole Moments 51

2.6 Separation Techniques 52

2.6.1 Size Exclusion Chromatography 52

2.6.2 Electrophoresis 53

2.7 Conclusion 53

References 54

3 Luminescent Dendrimers 67
Anne-Marie Caminade

3.1 Introduction 67

3.2 Dendrimers with Fluorescent Terminal Groups 68

3.2.1 Fully Substituted Dendrimers 68

3.2.2 Partially Substituted Dendrimers 69

3.3 Luminescent Group at the Core of Dendrimers and Energy/Light-Harvesting Properties 74

3.3.1 Organic Fluorophores as Cores 74

3.3.2 Porphyrins and Phthalocyanines as Cores 77

3.3.3 Metallic Cores 78

3.4 Fluorescent Groups inside the Structure of Dendrimers 79

3.5 Intrinsically Fluorescent Dendrimers 81

3.5.1 Fluorescent Groups throughout the Dendrimeric Structure 81

3.5.2 Fluorescence of Dendrimers without Known Fluorophores 86

3.6 Two-Photon-Excited Fluorescence of Dendrimers 86

3.7 Conclusion 89

References 90

4 Stimuli-Responsive Dendrimers 99
Anne-Marie Caminade

4.1 Introduction 99

4.2 Photoresponsive Dendrimeric Structures 100

4.2.1 Azobenzene-Containing Dendrimers and Dendrons 101

4.2.2 Other Types of Photoresponsive Dendrimers 108

4.3 Thermoresponsive Dendrimeric Structures 110

4.3.1 Thermoresponsive Properties of Dendrimers 110

4.3.2 Thermoresponsive Properties of Dendrons and Dendronized Polymers 112

4.4 Dendrimers Responsive to Solution Media Changes 114

4.4.1 pH-Responsive Dendrimers 114

4.4.2 Dendrimers Disassembly 115

4.5 Conclusion 117

References 118

5 Liquid Crystalline Dendrimers 125
Anne-Marie Caminade

5.1 Introduction 125

5.2 Mesogenic Groups as Terminal Functions of Dendrons 126

5.3 Mesogenic Groups as Terminal Functions of Dendrimers 131

5.4 Mesogenic Groups as Branches of Dendrimers 134

5.5 Conclusion 135

References 136

6 Dendrimers and Nanoparticles 141
Cédric-Olivier Turrin and Anne-Marie Caminade

6.1 Introduction 141

6.2 Dendrimers or Dendrons for Coating Nanoparticles 142

6.2.1 Dendronization of Nanoparticles by Ligand Exchange 142

6.2.2 Direct Synthesis of Dendronized Nanoparticles 147

6.2.3 Dendrimer Coated Nanoparticles 149

6.2.4 Nanocomposites with Interdendrimer Nanoparticles 151

6.3 Dendrimers as Templates for the Synthesis of

Dendrimer-Encapsulated Nanoparticles (DENs) 152

6.3.1 Catalysis with Dendrimer-Encapsulated Nanoparticles 153

6.3.2 Other Uses of Dendrimer-Encapsulated Nanoparticles 154

6.4 Conclusion and Perspectives 154

References 155

Part 2 Applications in Catalysis 163

7 Terminal Groups of Dendrimers as Catalysts for Homogeneous Catalysis 165
Armelle Ouali and Anne-Marie Caminade

7.1 General Introduction 165

7.1.1 The “Dendrimer Effect” 165

7.1.2 Recycling the Catalysts 166

7.2 Catalytic Organometallic Sites as Catalysts for Homogeneous Catalysis 167

7.2.1 Formation of C–X Bonds (X = C, N, O) 167

7.2.2 Addition Reactions on a C=X Double Bond (X = C, O) 175

7.2.3 Oxidation Reactions 177

7.3 Organocatalysis with Dendrimers 178

7.4 Conclusion 178

References 179

8 Catalytic Sites inside the Dendrimeric Structure for Homogeneous Catalysis 183
Armelle Ouali and Anne-Marie Caminade

8.1 Introduction 183

8.2 Catalytic Sites as the Core of Dendrimers 184

8.2.1 Dendrimers Bearing a Transition-Metal-Based Complex at the Core 184

8.2.2 Dendrimers Bearing an Organocatalyst at the Core 188

8.3 Catalytic Sites inside the Branches of Dendrimers 191

8.3.1 Formation of C–X Bonds (X = C, N, O) 191

8.3.2 Addition Reactions on a C=C Double Bond: Olefi n Hydrogenation 192

8.4 Conclusion 192

References 193

9 Dendrimers as Homogeneous Enantioselective Catalysts 197
Armelle Ouali and Anne-Marie Caminade

9.1 Introduction 197

9.2 Catalytic Organometallic Sites as Catalysts for Homogeneous Catalysis 198

9.2.1 Formation of C–X Bonds (X = C, N, O) 198

9.2.2 Addition Reactions on a C=X Double Bond (X = C, O) 204

9.3 Organocatalysis with Dendrimers 209

9.3.1 Aldolizations 209

9.3.2 Aza–Morita–Baylis–Hillmann Reactions 209

9.3.3 Transaminations 210

9.4 Conclusion 210

References 210

10 Catalysis with Dendrimers in Particular Media 215
Régis Laurent and Anne-Marie Caminade

10.1 Introduction 215

10.2 Two-Phase (Liquid–Liquid) Media 216

10.3 Catalysis in Ionic Liquids 219

10.4 Catalysis in Supercritical Media 220

10.5 Catalysis in Aqueous Media 221

10.6 Conclusion 234

References 234

11 Heterogeneous Catalysis with Dendrimers 239
Régis Laurent and Anne-Marie Caminade

11.1 Introduction 239

11.2 Catalysis with Dendrons Synthesized from a Solid Material 240

11.2.1 Silica as an Inorganic Support 240

11.2.2 Polymers and Resins as Organic Supports 248

11.3 Catalysis with Dendrons or Dendrimers Grafted on to a Solid Surface 254

11.4 Catalysis with Insoluble Dendrimers 257

11.5 Conclusion 260

References 261

Part 3 Applications for the Elaboration or Modification of Materials 267

12 Dendrimers inside Materials 269
Régis Laurent and Anne-Marie Caminade

12.1 Introduction 269

12.2 Dendrimers for the Elaboration of Gels 270

12.2.1 Dendrimers for the Elaboration of Supramolecular Hygrogels 270

12.2.2 Dendrimers for the Elaboration of Polymer-Type Hygrogels 273

12.2.3 Dendrimers for the Elaboration of Organogels 276

12.3 Dendrimers inside Silica Gels 280

12.4 Dendrimers inside Other Types of Materials 285

12.5 Dendrimers for the Elaboration of OLEDs 288

12.5.1 Fluorescent Dendrimers for the Elaboration of OLEDs 290

12.5.2 Phosphorescent Dendrimers for the Elaboration of OLEDs 295

12.6 Conclusion 298

References 299

13 Self-Assembly of Dendrimers in Layers 313
Béatrice Delavaux-Nicot and Anne-Marie Caminade

13.1 Introduction 313

13.2 Langmuir–Blodgett Films of Dendrons and Dendrimers 314

13.2.1 Poly(benzyl ether) Derivatives 316

13.2.2. Poly(amidoamine) and Poly(propyleneimine) Derivatives 319

13.2.3 Azobenzene Derivatives 320

13.2.4 Poly(carbosilane) Dendrimer Derivatives 321

13.2.5 Fullerene C60 Derivatives 322

13.2.6 Other Examples 325

13.3 Assemblies of Dendrons and Dendrimers on Solid Surfaces 326

13.3.1 Assembly of Dendrons and Dendrimers on Gold Surfaces 327

13.3.2 Assembly of Dendrons and Dendrimers on Silicon Substrates or Related Substrates 330

13.4 Several Routes for the Formation of Dendron or Dendrimer Multilayers 334

13.5 Nanoimprinting with Dendrons and Dendrimers on Solid Surfaces 342

13.5.1 Dendrimer-Based Self-Assembled Monolayers as Resists for Scanning Probe Lithography 342

13.5.2 Microprinting, Transfer Printing, and Dip-Pen Nanolithography with Dendrimers 344

13.6 Conclusion 350

References 351

14 Dendrimers as Chemical Sensors 361
Anne-Marie Caminade

14.1 Introduction 361

14.2 Dendrimers as Chemical Sensors in Solution 362

14.2.1 Porphyrins and Other Macrocyclic Derivatives as the Core or Branches of Dendrimeric Sensors 362

14.2.2 Terminal Groups of Dendrimers as Sensors in Solution 363

14.3 Dendrimers as Electrochemical Sensors 365

14.4 Dendrimers on Modifi ed Surfaces as Chemical Sensors 367

14.4.1 Dendrimers on Surfaces at the Interface with a Solution 367

14.4.2 Dendrimers on Surfaces at the Interface with a Vapor 368

14.5 Conclusion 370

References 370

15 Dendrimers as Biological Sensors 375
Anne-Marie Caminade

15.1 Introduction 375

15.2 Dendrimers as Sensors in Solutions of Biological Media 375

15.3 Detection by Electrochemical Methods 378

15.4 Dendrimers or Dendrons for DNA Microarrays 380

15.5 Dendrimers for Other Types of Biomicroarrays 383

15.6 Dendrimers on Other Types of Support 384

15.7 Dendrimers as Multiply Labeled Entities Connected to the Target 385

15.8 Conclusion 386

References 387

Part 4 Applications in Biology/Medicine 393

16 Dendrimers for Imaging 395
Cédric-Olivier Turrin and Anne-Marie Caminade

16.1 Introduction 395

16.2 Magnetic Resonance Imaging with Dendrimers 395

16.2.1 Paramagnetic Dendrimer-Based Contrast Agents 398

16.2.2 PARACEST Dendrimer-Based Contrast Agents 402

16.2.3 Superparamagnetic Dendrimer-Based Contrast Agents 402

16.2.4 Dendrimer-Based 129Xe HYPER-CEST MRI Contrast Agents 403

16.2.5 19F Dendrimer-Based MRI Contrast Agents 403

16.3 Other Types of Imaging with Dendrimers 403

16.3.1 Dendrimers for Optical Imaging 403

16.3.2 Dendrimers for Nuclear Medicine (NM) Imaging and Computed Tomography X-Ray Imaging (CT) 405

16.4 Conclusion and Perspectives 407

References 407

17 Dendrimers as Transfection Agents 413
Cédric-Olivier Turrin and Anne-Marie Caminade

17.1 Introduction 413

17.2 Gene Transfection with PAMAM Dendrimers 415

17.2.1 Pioneering Results 415

17.2.2 Gene Transfection with Surface-Modifi ed PAMAM 416

17.2.3 Gene Transfection with Core-Modifi ed PAMAM 418

17.2.4 Gene Transfection with PAMAM-Functionalized Nanoparticles 419

17.2.5 Gene Transfection with PAMAM-Like Hyperbranched Polymers 420

17.3 Gene Transfection with Other Dendrimers 421

17.3.1 Gene Transfection with PPI Dendrimers 421

17.3.2 Gene Transfection with Peptide-Based Dendrimers 422

17.3.3 Gene Transfection with Phosphorus-Based Dendrimers 423

17.3.4 Gene Transfection with Silane-Based Dendrimers 424

17.4 Conclusion and Perspective 426

References 426

18 Dendrimer Conjugates for Drug Delivery 437
Cédric-Olivier Turrin and Anne-Marie Caminade

18.1 Introduction 437

18.2 Improving Bioavailability with Dendrimers 438

18.3 Passive Targeting in Tumors with Dendrimer–Drug Conjugates 440

18.3.1 Dendrimer–Drug Bioconjugates and the EPR Effect 440

18.3.2 PEGylated Dendrimeric Scaffolds 442

18.4 Active Targeting with Site-Specifi c Dendrimer–Drug Conjugates 446

18.4.1 Addressing with Folic Acid (FA) 446

18.4.2 Addressing with Tumor-Homing Peptides 448

18.4.3 Addressing with Monoclonal Antibodies 449

18.5 Dendrimers for Photodynamic Therapy (PDT) 449

18.6 Dendrimers for Boron Neutron Capture Therapy (BNCT) 451

18.7 Conclusion and Perspectives 452

References 453

19 Encapsulation of Drugs inside Dendrimers 463
Cédric-Olivier Turrin and Anne-Marie Caminade

19.1 Introduction 463

19.2 From Dendritic Boxes to Dendrimer-Based Formulations 464

19.3 Improving Bioavailability with Dendrimers? 464

19.4 Toxicological Issues 465

19.5 Dendrimer-Based Formulations for Drug Delivery 466

19.5.1 Nontargeted Formulations 466

19.5.2 Supramolecular Assemblies Involving Surface Ionic Interactions 473

19.5.3 Targeted Formulations 475

19.6 Conclusion and Perspectives 477

References 477

20 Unexpected Biological Applications of Dendrimers and Specifi c Multivalency Activities 485
Cédric-Olivier Turrin and Anne-Marie Caminade

20.1 Introduction 485

20.2 Dendrimers and Multivalency 486

20.2.1 Multivalent Effects and Dendrimeric Effects 486

20.2.2 Glycodendrimers 487

20.3 Antimicrobial Dendrimers 488

20.3.1 Polycationic Dendrimers 489

20.3.2 Polyanionic Dendrimers 491

20.4 From Immunomodulation to Regenerative Medicine 494

20.4.1 Immunomodulation and Anti-Inflammation 494

20.4.2 Dendrimers and Regenerative Medicine 498

20.5 Conclusion and Perspectives 501

References 502

21 General Conclusions and Perspectives 511
Anne-Marie Caminade

Index 515

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 “The book is of high quality and recommended reading for anyone working with dendrimers or wanting to have a good reference book; rich in information, clearly organized and thoroughly referenced with topical primary publications.”  (Angewandte Chemie, 2012)

 

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