Supramolecular Chemistry in Water

Provides deep insight into the concepts and recent developments in the area of supramolecular chemistry in water Written by experts in their respective field, this comprehensive reference covers various aspects of supramolecular chemistry in water?from fundamental aspects to applications. It provides readers with a basic introduction to the current understanding of the properties of water and how they influence molecular recognition, and examines the different receptor types available in water and the types of substrates that can be bound. It also looks at areas to where they can be applied, such as materials, optical sensing, medicinal imaging, and catalysis. Supramolecular Chemistry in Water offers five major sections that address important topics like water properties, molecular recognition, association and aggregation phenomena, optical detection and imaging, and supramolecular catalysis. It covers chemistry and physical chemistry of water; water-mediated molecular recognition; peptide and protein receptors; nucleotide receptors; carbohydrate receptors; and ion receptors. The book also teaches readers all about coordination compounds; self-assembled polymers and gels; foldamers; vesicles and micelles; and surface-modified nanoparticles. In addition, it provides in-depth information on indicators and optical probes, as well as probes for medical imaging. -Covers, in a timely manner, an emerging area in chemistry that is growing more important every day -Addresses topics such as molecular recognition, aggregation, catalysis, and more -Offers comprehensive coverage of everything from fundamental aspects of supramolecular chemistry in water to its applications -Edited by one of the leading international scientists in the field Supramolecular Chemistry in Water is a one-stop-resource for all polymer chemists, catalytic chemists, biochemists, water chemists, and physical chemists involved in this growing area of research.

Autorentext

Stefan Kubik is Professor of Organic Chemistry at the University of Kaiserslautern. He has authored more than 1000 keywords for the chemistry encyclopedia Römpp-Online, acted as Guest Editor of the online themed collection of Organic & Biomolecular Chemistry on Supramolecular Chemistry in Water together with A. Dalla Cort and A. P. Davis, and is Associate Editor of the Journal of Inclusion Phenomena and Macrocyclic Chemistry.

Inhalt
Preface xv

**1 Water Runs Deep 1
**Nicholas E. Ernst and Bruce C. Gibb

1.1 The Control of Water 1

1.2 The Shape of Water 2

1.3 The Matrix of Life as a Solvent 4

1.4 Solvation Thermodynamics 6

1.5 The Three Effects 9

1.5.1 The Hydrophobic Effect 11

1.5.2 The Hofmeister Effect 19

1.5.3 The Reverse Hofmeister Effect 23

1.6 Conclusions and Future Work 24

Acknowledgments 25

References 25

**2 WaterCompatible Host Systems 35
**Frank Biedermann

2.1 General Overview 35

2.2 Acyclic Systems 36

2.2.1 Acyclic Molecular Recognition Units 36

2.2.2 Molecular Tweezers 38

2.2.3 Foldamers 39

2.2.4 Compartmentalized Structures Formed by SurfactantLike Molecules 40

2.3 Macrocyclic Receptors that Bind Charged Guests 42

2.3.1 Crown Ethers, Cryptands, and Spherands 42

2.3.2 Bambus[n]urils 44

2.3.3 Calix[n]arenes 45

2.3.4 Pillar[n]arenes 48

2.4 Macrocyclic Receptors that (also) Bind Noncharged Organic Guests 50

2.4.1 Cyclodextrins 50

2.4.2 Cucurbit[n]urils 54

2.4.3 Deep Cavitands 58Contents

2.4.4 Molecular Tubes 62

2.5 Practitioner's Guidelines for Choosing a WaterCompatible Host 64

2.5.1 Guest Binding Affinity and Selectivity 64

2.5.2 Availability/Scalability 65

2.5.3 Functionality 65

2.5.4 Solubility 66

2.5.5 Biocompatibility/Toxicity 67

References 67

**3 Artificial Peptide and Protein Receptors 79
**Joydev Hatai and Carsten Schmuck

3.1 Introduction 79

3.2 Peptide Recognition 79

3.2.1 Calixarenes 80

3.2.2 Guanidiniocarbonyl Pyrroles 80

3.2.3 Cucurbiturils 82

3.2.4 Metal Complexes 84

3.2.5 Phosphonates 86

3.2.6 ThioureaContaining Copolymers 87

3.3 Protein Recognition 88

3.3.1 Molecular Tweezer: Huntingtin Protein (htt) 89

3.3.2 Foldamer: Human Carbonic Anhydrase 89

3.3.3 Tetravalent Peptide: Tryptase 90

3.3.4 Semisynthetic Fusicoccin Derivative: 1433/Gab2 Protein 91

3.3.5 Ruthenium Complex: Cytochrome C 92

3.3.6 Nitrilotriacetic AcidPeptide Conjugate: HisTag Calmodulin 93

3.3.7 Cucurbit[7]uril: Native Insulin and Human Growth Hormone 95

3.3.8 Phosphonated Calix[6]arene: Cytochrome C 96

3.3.9 *p*Sulfonatocalixarene: Human Insulin 96

3.3.10 Multivalent Calixarene: PlateletDerived Growth Factor 97

3.4 Sensor Arrays for Proteins 99

3.4.1 Tripodal PeptideContaining Receptors: Proteins and Glycoproteins 99

3.4.2 Substituted Porphyrins: Proteins and Metalloproteins 100

3.4.3 Poly(*p*phenyleneethynylene)s: Proteins 101

3.4.4 Chemiluminescent Nanomaterials: Proteins and Cells 103

3.5 Combinatorial Fluorescent Molecular Sensors for Proteins 104

3.5.1 Probe for MMP, GST, and PDGF Protein Families 104

3.5.2 Probe for Amyloid Beta Proteins 107

3.6 Conclusions and Future Directions 108

References 109

**4 Recognition, Transformation, Detection of Nucleotides and Aqueous NucleotideBased Materials 115
**Isabel Pont, Cristina GalianaRosello, Alberto Lopera, Jorge GonzálezGarcía, and Enrique GarcíaEspaña

4.1 Introduction 115

4.2 Nucleotide Structures 118

4.3 Nucleotide Receptors 119

4.3.1 Receptors without Aromatic Units 119

4.3.2 Receptors with Aromatic Units 123

4.3.3 Metal Complexes as Nucleotide Receptors 131

4.3.4 Catalytic Aspects 134

4.4 Nucleotide Sensing 140

4.4.1 General Aspects 140

4.4.2 UVvis Sensing 140

4.4.3 Fluorescence Sensing 142 4.5 Soft Mate...