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Terpyridine-based Materials: For Catalytic, Optoelectronic and Life Science Applications

ISBN: 978-3-527-33038-6
542 pages
November 2011
Terpyridine-based Materials: For Catalytic, Optoelectronic and Life Science Applications (3527330380) cover image
In recent years, the utilization of terpyridines both in macromolecular structure assembly and device chemistry has exploded, enabling, for example, supramolecular polymer architectures with switchable chemical and physical properties as well as novel functional materials for optoelectronic applications such as light-emitting diodes and solar cells. Further applications include the usage of terpyridines and their metal complexes as catalysts for asymmetric organic reactions and, in a biological context, as anti-tumor agents or biolabels.

This book covers terpyridine-based materials topics ranging from syntheses, chemistry, and multinuclear metal complexes, right up to functionalized polymers, 3D-architectures, and surfaces.

The book is of interest for materials scientists, (in)organic chemists, polymer chemists, complex chemists, physical chemists, biochemists, and libraries.

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Preface ix

List of Abbreviations xi

1 Introduction 1

2 Synthesis, Properties, and Applications of Functionalized 2,2u:6u,2v-Terpyridines 13

2.1 Introduction 13

2.2 Basic Synthetic Strategies 13

2.3 Synthesis and Properties of 2,2u:6u,2v-Terpyridine Derivatives 19

2.4 2,2u:6u,2v-Terpyridines Symmetrically Substituted on the Outer Pyridine Rings 28

2.5 Ziessel-Type 2,2u:6u,2v-Terpyridines 31

2.6 Kro¨hnke-Type 2,2u:6u,2v-Terpyridines 38

2.7 Miscellaneous Terpyridine-Analogous Compounds 49

3 Chemistry and Properties of Terpyridine Transition Metal Ion Complexes 65

3.1 Introduction 65

3.2 Basic Synthetic Strategies and Characterization Tools 66

3.3 RuII and OsII Complexes 73

3.4 Iridium(III) Complexes with Terpyridine Ligands 107

3.5 Platinum(II) Mono(terpyridine) Complexes 115

4 Metallo-Supramolecular Architectures Based on Terpyridine Complexes 129

4.1 Introduction 129

4.2 Terpyridine-Containing Metallo-Macrocycles 130

4.3 The HETTAP Concept 148

4.4 Racks and Grids 154

4.5 Helicates 171

4.6 Rotaxanes and Catenanes 177

4.7 Miscellaneous Structures 182

5 p-Conjugated Polymers Incorporating Terpyridine Metal Complexes 199

5.1 Introduction 199

5.2 Metallo-Supramolecular Polymerization 200

5.3 Metallopolymers Based on p-Conjugated Bis(terpyridine)s 204

5.4 Main-Chain Metallopolymers Based on Terpyridine-Functionalized p-Conjugated Polymers 229

6 Functional Polymers Incorporating Terpyridine-Metal Complexes 241

6.1 Introduction 241

6.2 Polymers with Terpyridine Units in the Side-Chain 242

6.3 Polymers with Terpyridines within the Polymer Backbone 262

7 Terpyridine Metal Complexes and their Biomedical Relevance 319

7.1 Introduction 319

7.2 Terpyridine Metal Complexes with Biological Activity 320

8 Terpyridines and Nanostructures 399

8.1 Introduction 399

8.2 Terpyridines and Surface Chemistry 401

8.3 Terpyridines and Inorganic Nanomaterials 420

8.4 Terpyridines and Nano-Structured TiO2: Photovoltaic Applications 431

8.5 Organopolymeric Resins, Beads, and Nanoparticles 447

9 Catalytic Applications of Terpyridines and Their Transition Metal Complexes 459

9.1 Introduction 459

9.2 (Asymmetric) Catalysts in Organic Reactions 460

9.3 Electrocatalytic Oxidation and Reduction Processes 476

9.4 Photocatalytic Processes 480

10 Concluding Remarks 507

Index 509

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Ulrich S. Schubert performed his Ph.D. work under the supervision of Prof. C. D. Eisenbach (Bayreuth, Germany) and Prof. G. R. Newkome (Florida, USA). After a postdoctoral training with Prof. J.-M. Lehn at the Université Strasbourg (France), he moved to the Munich University of Technology (Germany) to obtain his habilitation in 1999. From 1999 to spring 2000, he held a temporary position as a professor at the Center for NanoScience at the LMU Munich. From June 2000 to March 2007, he was Full-Professor at the Eindhoven University of Technology (Chair for Macromolecular Chemistry and Nanoscience), the Netherlands. Since April 2007, he is Full-Professor at the Friedrich-Schiller-University Jena (Chair of Organic and Macromolecular Chemistry), Germany. He has published over 500 papers, 18 patents, and edited/written 5 scientific books.

Andreas Winter studied chemistry at the University of Dortmund (Germany), where he graduated in organic chemistry in 1999. In 2003, he received his Ph.D. in chemistry (University of Paderborn, Germany) for work on applications of the Mannich reaction in the synthesis of pyridine derivatives under supervision of Professor N. Risch, and stayed on as a postdoc. Subsequently, in 2005 he joined the group of Prof. U. S. Schubert (Eindhoven University of Technology, The Netherlands and Friedrich-Schiller University Jena, Germany). His research is focused on the synthesis of emissive and luminescent metallo-supramolecular assemblies.

George R. Newkome received his B.S. and Ph.D. in chemistry from Kent State University. He became a full professor in 1978 and Distinguished Research Master in 1982 at Louisiana State University. In 1986, he moved to the University of South Florida as Vice President for
Research and Professor of Chemistry, becoming a Distinguished Research Professor in 1992. In 2001, he became Vice President for Research and Dean of the Graduate School at The University of Akron. He is the Oelschlager Professor of Science and Technology and professor in the departments of Polymer Science and Chemistry. Currently, he is the President and CEO of the University of Akron`s Research Foundation and the Akron Innovation Campus. He has published over 430 papers, 45 patents, and edited/written over 15 scientific books and monographs.
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