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2.2 from Molecular to Supramolecular Chemistry

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2.2 from Molecular to Supramolecular Chemistry Supramolecular Multicomponent Architectures Alma Mater Studiorum Università di Bologna DOTTORATO DI RICERCA Scienze Farmaceutiche Ciclo XX Settore scientifico disciplinare di afferenza: CHIM/06 TITOLO TESI Supramolecular Hybrid Organic-Inorganic Multicomponent Architectures in Solution and on Surface Presentata dal Dott. Omar Pandoli Coordinatore Dottorato Relatore Prof. Maurizio Recanatini Prof. Gian Piero Spada Esame finale anno 2008 1 Self-Organization in Organic Chemistry 2 Supramolecular Multicomponent Architectures Contents Contents.............................................................................................................................3 Abstract.............................................................................................................................6 Acknowledgements...........................................................................................................7 1. Self-organization in biological chemistry.......................................................................9 1.1 Introduction ................................................................................................................9 1.2 Thesi organization.......................................................................................................9 1.3 How does life processe work?...................................................................................10 1.4 Where can we reconize the life in a system?.............................................................13 1.4.1 The ecological perspective ................................................................................14 1.4.2 Life defined in terms of DNA ...........................................................................14 1.4.3 Membranes-the foundation of cellular identity .................................................16 1.4.4 Self-generation ..................................................................................................16 1.4.5 The cellular network .........................................................................................18 1.4.6 Emergence of new order ...................................................................................19 1.4.7 Prebiotic evolution ............................................................................................20 1.4.8 Minimal life ......................................................................................................21 1.4.9 The elements of life ..........................................................................................22 1.4.10 Bubbles of minimal life ..................................................................................23 1.4.11 Catalysts and complexity ................................................................................25 1.4.12 What is life? ....................................................................................................26 1.5 Systems between complexity and creativity..............................................................27 1.5.1 Holism and emergence.......................................................................................28 1.5.2 General system theory........................................................................................29 1.5.3 Complexity Science...........................................................................................30 1.5.4 Multi-agent systems...........................................................................................31 1.5.5 Creative evolution .............................................................................................33 1.5.6 Multi-scale nature of complex systems..............................................................34 1.6 The dissipative structures..........................................................................................37 1.7 The holistic view of the eastern thought....................................................................42 1.8 Conclusion.................................................................................................................47 1.9 References.................................................................................................................48 3 Self-Organization in Organic Chemistry 2. Supramolecular Science as a science of informed matter...........................................53 2.1 Introduction ..............................................................................................................53 2.2 From molecular to supramolecular chemistry...........................................................56 2.3 Molecular recognition via base-pairing and self-organization..................................57 2.4 Dynamic chemical processes (Reversibility, Cooperativity and Flexibility)............66 2.5 From supramolecular chemistry to dynamic combinatorial chemistry (DCC)?........70 2.6 Conclusion.................................................................................................................79 2.7 References.................................................................................................................81 3. Self-assembling of Guanine Nucleoside derivatives: serendipity or programmed system?................................................................................................................................87 3.1 Introduction...............................................................................................................87 3.2 Supramoecular architecture generated by self-assembly of guanosine derivatives in solution and on the surface..............................................................................................90 3.2.1 Self-organization of guanosine derivatives in solution .....................................90 3.2.2 Self-organization of guanine and guanosine derivatives on the solid surface. .98 3.3 Nanostructures self-assembled as versatile scaffold to control self-organization material..........................................................................................................................110 3.4 Conclusion...............................................................................................................121 3.5 References...............................................................................................................122 4. Multicomponents supramolecular hybrid architectures in solution and on the surface................................................................................................................................125 4.1 Introduction.............................................................................................................125 4.2 Reversible interconversion between a supramolecular polymer and a discrete octameric species from a guanosine derivative by dynamic cation binding and release .......................................................................................................................................126 4.3 Self-assembly of an alkylated guanosine derivative into ordered supramolecular nanoribbons in solution and on solid surfaces ..............................................................130 4.4 Cation-templated self-assembly of a lipophilic alkoxy guanosine: solution structure + + of a Ag G8 octamer or Ag G16 hexadecamer?...............................................................143 4.5 Collaboration activity with Rolic Techlonogy Ltd , Basel, Swiss. .........................157 4.6 Conclusion...............................................................................................................157 5.7 References...............................................................................................................158 4 Supramolecular Multicomponent Architectures 5. Future directions..........................................................................................................163 5.1 Arabian geometric patterns: images for graphic resource, inspiration and funny design.............................................................................................................................164 5.2 References...............................................................................................................166 5.3 Curriculum Vitae.....................................................................................................167 5 Self-Organization in Organic Chemistry Abstract Supramolecular architectures can be built-up from a single molecular component (building block) to obtain a complex of organic or inorganic interactions creating a new emergent condensed phase of matter, such as gels, liquid crystals and solid crystal. Further the generation of multicomponent supramolecular hybrid architecture, a mix of organic and inorganic components, increases the complexity of the condensed aggregate with functional properties useful for important areas of research, like material science, medicine and nanotechnology. One may design a molecule storing a recognition pattern and programming a informed self-organization process enables to grow-up into a hierarchical architecture. From a molecular level to a supramolecular level, in a bottom-up fashion, it is possible to create a new emergent structure-function, where the system, as a whole, is open to its own environment to exchange energy, matter and information. “The emergent property of the whole assembly is superior to the sum of a singles parts”. In this thesis I present new architectures and functional materials built
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