Prof. Andrey A. Fokin is Full Professor and Head of the Department of Organic Chemistry and Technology at National Technical University "Igor Sikorsky Kiyv Polytechnic Institute" (Ukraine). He has been a visiting professor at the Universities of Minnesota and Georgia (USA) as well as in Giessen (Germany). His research mostly concentrates on the combination of computational and experimental studies with applications in organic, physical-organic, medical, agricultural chemistry and nanotechnology.Dr. Marina Sekutor is senior research associate in the Division of Organic Chemistry and Biochemistry at the Ruder Boskovic Institute (Zagreb, Croatia). She was a postdoctoral Alexander-von-Humboldt fellow in the group of Prof. Schreiner at the Justus Liebig University Giessen (Germany) and a visiting scientist at the University of Maryland (USA). Her research interests include supramolecular host-guest chemistry of polycyclic compounds and the use of diamondoid derivatives in materials science.Prof. Peter R. Schreiner is Professor of Organic Chemistry and Liebig-Chair at the Institute of Organic Chemistry at Justus Liebig University Giessen (Germany). His research interests include organic reaction dynamics and reactive intermediates, quantum mechanical tunneling as well as London dispersion interactions as probed in the realm of nanodiamonds and organocatalysis. He is an Editor for the Journal of Computational Chemistry, WIRES - Computational Molecular Sciences, and the Beilstein Journal of Organic Chemistry.

• Preface ixAbbreviations xiAcknowledgments xvAuthor Biographies xvii1 Description of Diamondoids 11.1 Nomenclature 21.2 Strain 51.3 Preparation of Diamondoids 81.4 Physical Properties of Diamondoids 141.5 Spectroscopy of Diamondoids 181.6 Ionization Potentials 231.7 Electron Affinities 241.8 Vibrational Spectroscopy 252 Naturally Occurring Diamondoids 352.1 Diamondoid Occurrence in the Earth’s Crust 382.2 Diamondoids in Geochemical Studies 402.3 Diamondoid Formation in the Earth’s Crust 422.4 Large-scale Isolation of Natural Diamondoids 442.5 Alternative Natural Sources of Diamondoids 482.6 Other Diamondoid Derivatives in Nature 503 Diamondoids as Alkane CH Activation Models 634 Preparative Diamondoid Functionalizations 754.1 Halogenations 754.2 Diamondoid Alcohols and Ketones 834.3 Carboxylic Acids and Their Derivatives 984.4 Nitrogen-Containing Compounds 1034.5 Phosphorous- and Sulfur-Containing Compounds 1084.6 Single Electron Oxidations of Diamondoids 1134.7 Other Diamondoid Derivatives 1185 Diamondoid Self-Assembly 1375.1 Adamantane-Containing SAMs on Surfaces 1375.2 Higher Diamondoids for SAM Formation 1465.3 Pristine Diamondoids on Surfaces 1575.4 Other Applications of Diamondoid SAM Materials 1575.5 Adamantane-stabilized Metal Nanoparticles 1606 Growing Diamond Structures from Diamondoids Via Seeding 1716.1 Diamondoid-Promoted Growth of Diamond Under HT-HP or CVD Conditions 1716.2 Higher Diamondoids for Diamond Nucleation 1776.3 Diamond Growth Inside Nanotubes 1807 Diamondoid Polymers 1937.1 Polymers Based on 1-Adamantyl-1-adamantane (1ADAD) 1947.2 Polymers Based on Monofunctionalized Diamantanes 1977.3 Polymers Based on Difunctionalized Diamantanes 1998 Diamondoids in Catalysis 2139 Medicinal Compounds 23910 Supramolecular Architectures 25111 Diamondoid Oligomers 27911.1 Saturated Diamondoid Oligomers 27911.2 Unsaturated Oligomers 28712 Doped Diamondoids 30512.1 @-Doping 30612.2 Internal Doping 30812.3 External Doping 31813 Perspective 339References 340Index 343

Prof. Andrey A. Fokin is Full Professor and Head of the Department of Organic Chemistry and Technology at National Technical University "Igor Sikorsky Kiyv Polytechnic Institute" (Ukraine). He has been a visiting professor at the Universities of Minnesota and Georgia (USA) as well as in Giessen (Germany). His research mostly concentrates on the combination of computational and experimental studies with applications in organic, physical-organic, medical, agricultural chemistry and nanotechnology.Dr. Marina Sekutor is senior research associate in the Division of Organic Chemistry and Biochemistry at the Ruder Boskovic Institute (Zagreb, Croatia). She was a postdoctoral Alexander-von-Humboldt fellow in the group of Prof. Schreiner at the Justus Liebig University Giessen (Germany) and a visiting scientist at the University of Maryland (USA). Her research interests include supramolecular host-guest chemistry of polycyclic compounds and the use of diamondoid derivatives in materials science.Prof. Peter R. Schreiner is Professor of Organic Chemistry and Liebig-Chair at the Institute of Organic Chemistry at Justus Liebig University Giessen (Germany). His research interests include organic reaction dynamics and reactive intermediates, quantum mechanical tunneling as well as London dispersion interactions as probed in the realm of nanodiamonds and organocatalysis. He is an Editor for the Journal of Computational Chemistry, WIRES - Computational Molecular Sciences, and the Beilstein Journal of Organic Chemistry.

• Preface ixAbbreviations xiAcknowledgments xvAuthor Biographies xvii1 Description of Diamondoids 11.1 Nomenclature 21.2 Strain 51.3 Preparation of Diamondoids 81.4 Physical Properties of Diamondoids 141.5 Spectroscopy of Diamondoids 181.6 Ionization Potentials 231.7 Electron Affinities 241.8 Vibrational Spectroscopy 252 Naturally Occurring Diamondoids 352.1 Diamondoid Occurrence in the Earth’s Crust 382.2 Diamondoids in Geochemical Studies 402.3 Diamondoid Formation in the Earth’s Crust 422.4 Large-scale Isolation of Natural Diamondoids 442.5 Alternative Natural Sources of Diamondoids 482.6 Other Diamondoid Derivatives in Nature 503 Diamondoids as Alkane CH Activation Models 634 Preparative Diamondoid Functionalizations 754.1 Halogenations 754.2 Diamondoid Alcohols and Ketones 834.3 Carboxylic Acids and Their Derivatives 984.4 Nitrogen-Containing Compounds 1034.5 Phosphorous- and Sulfur-Containing Compounds 1084.6 Single Electron Oxidations of Diamondoids 1134.7 Other Diamondoid Derivatives 1185 Diamondoid Self-Assembly 1375.1 Adamantane-Containing SAMs on Surfaces 1375.2 Higher Diamondoids for SAM Formation 1465.3 Pristine Diamondoids on Surfaces 1575.4 Other Applications of Diamondoid SAM Materials 1575.5 Adamantane-stabilized Metal Nanoparticles 1606 Growing Diamond Structures from Diamondoids Via Seeding 1716.1 Diamondoid-Promoted Growth of Diamond Under HT-HP or CVD Conditions 1716.2 Higher Diamondoids for Diamond Nucleation 1776.3 Diamond Growth Inside Nanotubes 1807 Diamondoid Polymers 1937.1 Polymers Based on 1-Adamantyl-1-adamantane (1ADAD) 1947.2 Polymers Based on Monofunctionalized Diamantanes 1977.3 Polymers Based on Difunctionalized Diamantanes 1998 Diamondoids in Catalysis 2139 Medicinal Compounds 23910 Supramolecular Architectures 25111 Diamondoid Oligomers 27911.1 Saturated Diamondoid Oligomers 27911.2 Unsaturated Oligomers 28712 Doped Diamondoids 30512.1 @-Doping 30612.2 Internal Doping 30812.3 External Doping 31813 Perspective 339References 340Index 343

Prof. Andrey A. Fokin is Full Professor and Head of the Department of Organic Chemistry and Technology at National Technical University "Igor Sikorsky Kiyv Polytechnic Institute" (Ukraine). He has been a visiting professor at the Universities of Minnesota and Georgia (USA) as well as in Giessen (Germany). His research mostly concentrates on the combination of computational and experimental studies with applications in organic, physical-organic, medical, agricultural chemistry and nanotechnology.Dr. Marina Sekutor is senior research associate in the Division of Organic Chemistry and Biochemistry at the Ruder Boskovic Institute (Zagreb, Croatia). She was a postdoctoral Alexander-von-Humboldt fellow in the group of Prof. Schreiner at the Justus Liebig University Giessen (Germany) and a visiting scientist at the University of Maryland (USA). Her research interests include supramolecular host-guest chemistry of polycyclic compounds and the use of diamondoid derivatives in materials science.Prof. Peter R. Schreiner is Professor of Organic Chemistry and Liebig-Chair at the Institute of Organic Chemistry at Justus Liebig University Giessen (Germany). His research interests include organic reaction dynamics and reactive intermediates, quantum mechanical tunneling as well as London dispersion interactions as probed in the realm of nanodiamonds and organocatalysis. He is an Editor for the Journal of Computational Chemistry, WIRES - Computational Molecular Sciences, and the Beilstein Journal of Organic Chemistry.

• Preface ixAbbreviations xiAcknowledgments xvAuthor Biographies xvii1 Description of Diamondoids 11.1 Nomenclature 21.2 Strain 51.3 Preparation of Diamondoids 81.4 Physical Properties of Diamondoids 141.5 Spectroscopy of Diamondoids 181.6 Ionization Potentials 231.7 Electron Affinities 241.8 Vibrational Spectroscopy 252 Naturally Occurring Diamondoids 352.1 Diamondoid Occurrence in the Earth’s Crust 382.2 Diamondoids in Geochemical Studies 402.3 Diamondoid Formation in the Earth’s Crust 422.4 Large-scale Isolation of Natural Diamondoids 442.5 Alternative Natural Sources of Diamondoids 482.6 Other Diamondoid Derivatives in Nature 503 Diamondoids as Alkane CH Activation Models 634 Preparative Diamondoid Functionalizations 754.1 Halogenations 754.2 Diamondoid Alcohols and Ketones 834.3 Carboxylic Acids and Their Derivatives 984.4 Nitrogen-Containing Compounds 1034.5 Phosphorous- and Sulfur-Containing Compounds 1084.6 Single Electron Oxidations of Diamondoids 1134.7 Other Diamondoid Derivatives 1185 Diamondoid Self-Assembly 1375.1 Adamantane-Containing SAMs on Surfaces 1375.2 Higher Diamondoids for SAM Formation 1465.3 Pristine Diamondoids on Surfaces 1575.4 Other Applications of Diamondoid SAM Materials 1575.5 Adamantane-stabilized Metal Nanoparticles 1606 Growing Diamond Structures from Diamondoids Via Seeding 1716.1 Diamondoid-Promoted Growth of Diamond Under HT-HP or CVD Conditions 1716.2 Higher Diamondoids for Diamond Nucleation 1776.3 Diamond Growth Inside Nanotubes 1807 Diamondoid Polymers 1937.1 Polymers Based on 1-Adamantyl-1-adamantane (1ADAD) 1947.2 Polymers Based on Monofunctionalized Diamantanes 1977.3 Polymers Based on Difunctionalized Diamantanes 1998 Diamondoids in Catalysis 2139 Medicinal Compounds 23910 Supramolecular Architectures 25111 Diamondoid Oligomers 27911.1 Saturated Diamondoid Oligomers 27911.2 Unsaturated Oligomers 28712 Doped Diamondoids 30512.1 @-Doping 30612.2 Internal Doping 30812.3 External Doping 31813 Perspective 339References 340Index 343