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2015 | Buch

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Hydrogen Bonded Supramolecular Structures

herausgegeben von: Zhan-Ting Li, Li-Zhu Wu

Verlag: Springer Berlin Heidelberg

Buchreihe : Lecture Notes in Chemistry

Enthalten in: Springer Professional "Wirtschaft+Technik" , Springer Professional "Technik"

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Über dieses Buch

This book covers the advances in the studies of hydrogen-bonding-driven supramolecular systems made over the past decade. It is divided into four parts, with the first introducing the basics of hydrogen bonding and important hydrogen bonding patterns in solution as well as in the solid state. The second part covers molecular recognition and supramolecular structures driven by hydrogen bonding. The third part introduces the formation of hollow and giant macrocycles directed by hydrogen bonding, while the last part summarizes hydrogen bonded supramolecular polymers.

This book is designed to bring together in a single volume the many important aspects of hydrogen bonding supramolecular chemistry and will be a valuable resource for graduates and researchers working in supramolecular and related sciences.

Zhan-Ting Li, PhD, is a Professor of Organic Chemistry at the Department of Chemistry, Fudan University, China.

Li-Zhu Wu, PhD, is a Professor of Organic Chemistry at the Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, China.

Inhaltsverzeichnis

Frontmatter

Chapter 1. Hydrogen Bonding Motifs: New Progresses

Abstract

This chapter summarizes the important and typical intramolecular and intermolecular hydrogen bonding motifs. The capacities of hydrogen bonding donors and acceptors are first discussed. Representative and new single hydrogen bonding motifs, particularly those formed by weak hydrogen bonding acceptors and hydrocarbon hydrogen bonding donors reported in the last decade, are then described. In the last section, intermolecular double, triple, quadruple, sextuple, heptuple, and octuple hydrogen bonding motifs are presented.

Dan-Wei Zhang, Hui Wang, Zhan-Ting Li

Chapter 2. Understanding of Noncovalent Interactions Involving Organic Fluorine

Abstract

Due to the unpredictable nature of organic fluorine in its participation in the formation of different supramolecular motifs which concomitantly influences the physicochemical properties of the compounds of interest, the study of noncovalent interactions involving organic fluorine will always be an expanding area of research amongst the scientific community. The participation of organic fluorine in the formation of intermolecular interactions has always been questioned. In this book chapter, we provide insights into new structural features, nature, and energetics associated with intermolecular interactions, namely C–H···F–C, C–F···F–C, C–F···X (N, O, S, halogen) from researchers across the world. The studies show that interactions involving fluorine are ubiquitous and play a central role in the existence of diversified solid state properties, namely polymorphism, crystal engineering, and cocrystallization.

Piyush Panini, Deepak Chopra

Chapter 3. Hydrogen Bonding in Supramolecular Crystal Engineering

Abstract

This chapter emphases the important role of hydrogen bonding in crystal engineering for preparing fascinating architectures and engineering desired properties. The relatively high directionality and strength of hydrogen bonds make the prediction and control of molecular orientation in organic solids practical and reliable. Especially, strong hydrogen bonds like O–H···O, O–H···N, and N–H···O interactions are more useful. The introduction of supramolecular synthons and retrosynthesis theory has helped crystal chemists a lot in understanding and designing more complex structures. A large number of crystal structures reported in Cambridge Structure Database (CSD) provided a helpful tool for searching and analyzing specific interaction modes. Up to now, with the development of basic concepts and principles and the wide applications, the subject of crystal engineering has matured. Various intriguing structures and complicated entanglements have been constructed based on hydrogen bonds, such as nanocapsules, nanotubes, and n-Borromean arrayed topologies. The crystal engineering strategy has lent chemists the ability to control solid state reactions regio- and stereo-specifically and improve the physicochemical properties of drugs using pharmaceutical cocrystals. In addition, it will be seen that hydrogen bonding can also be used to prepare robust porous materials for gas adsorption and separation.

Lian-Cheng Wang, Qi-Yu Zheng

Chapter 4. Hydrogen Bonding-Mediated Self-assembly of Aromatic Supramolecular Duplexes

Abstract

We highlight in this chapter the most recent advance in the construction of supramolecular duplexes from aromatic components mediated by hydrogen bonding. We put the emphasis on the design strategies and properties of oligoamide and oligohydrazide-based systems. Based on the analysis of the available examples, we summarize a set of general guidelines for the design of hydrogen bonding-mediated molecular duplexes.

Yong Yang, Chuan-Feng Chen

Chapter 5. Hydrogen Bonding-Driven Anion Recognition

Abstract

Anion binding is a timely research field that is developing rapidly because anions play important roles in many areas. Hydrogen (H)-bonding has proven to be a highly effective tool in binding anions due to its directionality and strength. This chapter focuses on the H-bonding-driven anion recognition by neutral receptors that bear H-bond donors, such as (thio)amide, (thio)urea, pyrroles, acidic CHs, and hydroxyl groups. The design and synthesis of receptors based on these binding units have been explored by a number of research groups to achieve a better binding for different kinds of anions in terms of binding constant and selectivity. Recent progress in these aspects is summarized in this chapter. In particular, we emphasize the properties of XH∙∙∙anion (X = N, C, O) H-bonds in the crystal structure of anion complexes, such as the binding mode, the number of H-bonds, and the H-bond lengths and angles. Some solution studies of anion binding including the association constants are also presented. The aim is to provide an overview of this field, including the utilization of H-bonding in anion binding/coordination, the design strategies of the receptors, and their potential applications.

Liping Cao, Jie Zhao, Dong Yang, Xiao-Juan Yang, Biao Wu

Chapter 6. Formation of Hydrogen-Bonded Self-assembled Structures in Polar Solvents

Abstract

In this chapter a few recent examples of H-bond driven supramolecular assemblies in aqueous and polar organic media are discussed. H-bonding has been extensively utilized in the past for the generation of various nanostructures but those studies were mainly restricted to non-polar organic media. In recent years, however, the attention has shifted to obtain similar assemblies also in aqueous and polar media. The main principles that have been employed for this purpose are shielding of H-bonds from competing solvent molecules by hydrophobic residues or strengthening them by additional interactions such as electrostatic interactions or π–π stacking. The examples discussed here highlight the key structural features of the building blocks used and present an overview of the different types of nanostructures obtained with an emphasis on the functional properties of the resulting materials.

Supratim Banerjee, Carsten Schmuck

Chapter 7. Hydrogen Bonded Capsules: Chemistry in Small Spaces

Abstract

This chapter reports the behavior of molecules confined to spaces barely large enough to accommodate them—encapsulation complexes. The molecules respond to the limited spaces with adapted shapes, prolonged contacts, and intensified interactions including accelerated reactions. Emphasis is placed on reversible encapsulation and the differences between molecules in free solution and those in hydrogen-bonded capsules.

Li Juan Liu, Julius Rebek Jr

Chapter 8. Hydrogen Bonded Organic Nanotubes

Abstract

This chapter summarizes the application of hydrogen bonding in the construction of organic nano-tubes. Different tubular systems, including unimolecular nanotubes formed from helical and cavity-possessing molecules, and supramolecular nanotubes assembled from the bundles of rod-like molecules, the stacking of macrocyclic molecules, and the aggregation of wedge-like molecules through hydrogen bonding, are discussed by introducing typical examples.

Jun-Li Hou

Chapter 9. H-Bonding-Assisted One-Pot Macrocyclization for Rapid Construction of H-Bonded Macrocyclic Aromatic Foldamers

Abstract

The study of macrocycles has crossed many disciplines such as chemistry, physics, biology, medicine, and engineering with many research areas concentrating on specific and selective molecular recognition, self-organization and its already demonstrated, and other promising applications. Compared to traditional strategies to synthesize macrocycles with widely ranging structures using such as templated cyclization or dynamic covalent bond formation, the use of multiple-center intramolecular H-bonds for the efficient one-pot H-bonding-assisted construction of macrocycles of varying structures and functions is among the newest and the most noteworthy additions to the toolbox for macrocycle synthesis. This strategy has allowed the creation of sizable interior cavities of as small as 1.4 Å and as large as 15 Å in radius in these H-bonded macrocycles with a number of them expressing tailor-made functions. This chapter summarizes the recent works on such “greener” syntheses of H-bonded macrocycles which help to create a whole new dimension of scientific research, markedly expanding both the structural and functional repertoires of shape-persistent macrocycles that offer a new bottom-up strategy for constructing functional architectures and materials.

Huaqiang Zeng

Chapter 10. Hydrogen-Bonded Supramolecular Polymers

Abstract

Supramolecular polymers constructed by different kinds of low-molecular-weight monomers or high-molecular-weight conventional polymeric species based on hydrogen bonding interactions have attracted more and more attention due to their fascinating and unconventional chemical and physical properties. A series of multiple hydrogen-bonding building blocks are described herein, which make the expansion of the research field of hydrogen-bonded supramolecular polymers and allow the fabrication of more new and functional supramolecular polymers. This chapter focuses on linear hydrogen-bonded supramolecular polymers and networks which are described in three parts. The first part is the main-chain supramolecular polymers, in which the polymeric backbone is constructed by noncovalently bonded low-molecular-weight monomers. The second part is the conventional polymer-based supramolecular polymers, in which the main polymeric backbone part is constructed by covalently bonded conventional polymer, but functionalized by hydrogen-bonding motifs. The last part is supramolecular polymers constructed by orthogonal hydrogen bonding-driven self-assembly and other noncovalent interactions.

Chen Lin, Tangxin Xiao, Leyong Wang

Titel: Hydrogen Bonded Supramolecular Structures
herausgegeben von: Zhan-Ting Li
Li-Zhu Wu
Verlag: Springer Berlin Heidelberg
Electronic ISBN: 978-3-662-45756-6
Print ISBN: 978-3-662-45755-9
DOI: https://doi.org/10.1007/978-3-662-45756-6

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