Helicenes : synthesis, properties, and applications / / edited by Jeanne Crassous, Irena G. Stara, and Ivo Stary

• Pubblicazione: Weinheim, Germany, : Wiley-VCH, , [2023]; ©2023
• Descrizione fisica: 1 online resource (563 pages)
• Disciplina: 547
• Soggetto topico: Aromatic compounds; Polycyclic compounds
• Persona (resp. second.): StaraIrena G.; CrassousJeanne; StaryIvo
• Nota di bibliografia: Includes bibliographical references and index.
• Nota di contenuto: Cover -- Title Page -- Copyright -- Contents -- Preface -- Chapter 1 The Photochemical Approach to Helicenes -- 1.1 Introduction -- 1.2 General Features -- 1.3 Photochemical Preparation of Carbohelicenes -- 1.3.1 Oxidative Photocyclizations of Unsubstituted Carbo[n]helicenes -- 1.3.2 Oxidative Photocyclizations of Substituted Carbo[n]helicenes -- 1.3.3 Oxidative Photocyclizations of Benzocarbo[n]helicenes -- 1.3.4 Oxidative Photocyclizations of Multiple Carbo[n]helicenes -- 1.3.5 Eliminative Photocyclizations of Carbo[n]helicenes -- 1.4 Photochemical Preparation of Heterohelicenes -- 1.4.1 Azahelicenes -- 1.4.2 Thiahelicenes -- 1.4.3 Phosphahelicenes and Other Heterohelicenes -- 1.5 Photochemical Preparation of Helicene‐Like Molecules -- 1.6 Photochemical Transformations of Helicenes -- 1.7 Conclusions -- References -- Chapter 2 Synthesis of Helicenes by [2 + 2 + 2] Cycloisomerization of Alkynes and Related Systems -- 2.1 Introduction -- 2.2 Helicenes via [2 + 2 + 2] Cycloisomerization of π‐Electron Systems -- 2.2.1 Intramolecular [2 + 2 + 2] Cycloisomerization -- 2.2.2 Intermolecular [2 + 2 + 2] Cycloisomerization -- 2.3 Carbo‐ and Heterohelicenes -- 2.3.1 Carbohelicenes -- 2.3.2 Azahelicenes -- 2.3.3 Azoniahelicenes -- 2.3.4 Oxahelicenes -- 2.3.5 Sila‐, Phospha‐, and Thiahelicenes -- 2.4 Functionalized Helicenes -- 2.5 Asymmetric Synthesis of Nonracemic Helicenes -- 2.5.1 Stoichiometric Diastereoselective Synthesis -- 2.5.2 Catalytic Enantioselective Synthesis -- 2.6 Advanced Helicene Architectures -- 2.7 Summary and Outlook -- 2.8 Abbreviations -- References -- Chapter 3 Enantioselective Synthesis of Helicenes -- 3.1 Introduction -- 3.2 Metal‐Catalyzed [2 + 2 + 2] Cycloaddition -- 3.2.1 Ni‐ and Co‐catalyzed [2 + 2 + 2] Cycloaddition -- 3.2.2 Rh‐ and Ir‐Catalyzed [2 + 2 + 2] Cycloaddition -- 3.2.3 Pd‐catalyzed [2 + 2 + 2] Cycloaddition. ; 3.3 Metal‐catalyzed Hydroarylation -- 3.4 Metal‐catalyzed Oxidative Annulation -- 3.5 Organocatalyzed Annulation -- 3.6 Conclusion -- References -- Chapter 4 Cationic Triarylcarbenium Helicenes: Synthesis, Resolution, and Applications -- 4.1 Introduction -- 4.2 Synthesis and Resolution of Cationic [4]‐, [5]‐, and [6]Helicenes -- 4.2.1 [4]Helicenes -- 4.2.2 [6]Helicenes -- 4.2.3 [5]Helicenes -- 4.3 Regioselective Functionalization -- 4.3.1 Generalities: Nomenclature -- 4.3.2 Late‐stage Functionalization -- 4.3.2.1 North Functionalization of Cationic [4]‐ and [6]Helicenes -- 4.3.2.2 South Functionalization of Cationic [4]‐ and [6]helicenes -- 4.3.2.3 Tropical Functionalization Cationic [6]Helicenes -- 4.3.2.4 Central Nucleophilic Additions on [4]‐, [5]‐, and [6]Helicenes -- 4.3.3 Early‐stage Equatorial Functionalization of [4]Helicene -- 4.4 Structural Properties -- 4.4.1 Helical Pitch and Configurational Stability -- 4.4.2 pKR+ and Chemical Stability -- 4.5 Optical and Chiroptical Properties and Applications of Cationic Helicenes -- 4.5.1 Absorption and Fluorescence Properties -- 4.5.2 Chiroptical Properties -- 4.5.3 Biological Applications -- 4.5.3.1 Interaction with DNA -- 4.5.3.2 Cellular Imaging -- 4.5.4 Applications Based on Redox Chemistry -- 4.5.4.1 Generalities -- 4.5.4.2 Electrochemiluminescence -- 4.5.4.3 Thin Film Voltammetry -- 4.5.4.4 Stable Radicals -- 4.5.5 Organometallic Chemistry and Photocatalysis -- 4.5.6 Spintronics -- 4.6 Conclusion -- References -- Chapter 5 Organometallic and Coordination Chemistry of Helicenes -- 5.1 Introduction -- 5.2 Coordination Chemistry -- 5.2.1 Coordination of Monodentate Helicenes -- 5.2.2 Coordination of Bidentate Helicenes -- 5.2.3 Coordination of Polydentate Helicenes -- 5.3 Organometallic Chemistry -- 5.3.1 Metal‐vinyl‐ and Metal‐ethynyl‐helicenes -- 5.3.1.1 Metal‐vinyl‐helicene Complexes (Ru, Os). ; 5.3.1.2 Metal‐ethynyl‐helicene Complexes (Fe, Ru, Au) -- 5.3.2 Cyclometalated Helicenic Complexes -- 5.3.2.1 Cyclometalated Helicenic Complexes Bearing C^N Chelate Ligands (Pt, Ir, Os) -- 5.3.2.2 Cyclometalated Helicenic Complexes Bearing NHCs (Ir, Re) and Related Complexes -- 5.3.3 Sandwich‐type Helicenic Complexes -- 5.4 Conclusion -- References -- Chapter 6 Tetrathiahelicenes: An Infinite Source of Inspiration -- 6.1 Introduction -- 6.2 Synthesis of 7‐TH Scaffold -- 6.2.1 Oxidative Cyclization of Bis(benzodithienyl)ethenes -- 6.2.1.1 Photochemical Oxidative Cyclization -- 6.2.2 Annulation of 3,3′‐Bis(benzo[1,2‐b:4,3‐b′]dithiophene) Derivatives -- 6.3 Functionalization -- 6.4 Resolution of Enantiomers -- 6.4.1 Chiral HPLC -- 6.4.2 Enzymatic Resolution -- 6.4.3 Formation of Diastereoisomers -- 6.4.4 Kinetic Resolution -- 6.5 Electrochemical Properties and Applications of Tetrathiahelicenes -- 6.5.1 Investigation of Tetrathiahelicene Electroactivity on a Systematic Compound Series -- 6.5.2 Investigation of Electronic Properties of Electroactive 7‐TH Adducts With Advanced Functional Properties -- 6.5.3 Application of 7‐TH‐based Inherently Chiral Films for Enantioselective Electroanalysis -- 6.6 Computational Studies on Tetrathiahelicenes -- 6.6.1 General Remarks -- 6.6.2 Electron‐Detached and Attached States of 7‐TH Phosphorus Derivatives -- 6.6.3 Optical Properties of Chiral Tetrathiahelicene‐Based Alkyl Phosphine−Borane Complexes -- 6.6.4 Computational Study on Vibrational Raman Optical Activity of Helicenes -- 6.7 Materials -- 6.7.1 NLO -- 6.7.2 Self‐Assembly -- 6.7.3 Molecular Spring -- 6.7.4 Photoswitches -- 6.8 Catalysis -- 6.8.1 Organometallic Catalysis -- 6.8.2 Organocatalysis -- 6.9 Interaction with Biomolecules -- 6.9.1 Chiral Recognition of Biomolecules -- 6.9.2 Delivery Systems for 7‐TH -- 6.10 Conclusion -- References. ; Chapter 7 Synthesis and Properties of Helicenes with Small Numbers of Benzene Rings -- 7.1 Helicenes with Small Numbers of Benzene Rings -- 7.1.1 Helicenes -- 7.2 Synthesis of Helicene Derivatives -- 7.2.1 Tetracyclic Helicenes -- 7.2.2 Bicyclic Helicenes -- 7.3 Noncovalent Bond Interactions and Chiral Recognition -- 7.3.1 Complexation and Chiral Recognition by Oligosaccharides in Water -- 7.3.2 Formation of Langmuir-Blodgett (LB) Films -- 7.3.3 Charge Transfer (CT) Complexation -- 7.3.4 Formation of Self‐assembly Gel -- 7.4 Asymmetric Catalysis -- 7.5 Electronic Properties -- 7.5.1 Reversible Switching of Charge Injection Barriers Using Helicenedithiol -- 7.5.2 Ferroelectricity -- 7.6 Interactions with Biological Macromolecules -- 7.6.1 Nucleic Acid Binding -- 7.6.2 Enzyme Inhibitor -- 7.7 Separation Involving Aggregation of Helicene‐Grafted Nanoparticles -- 7.7.1 Separation of Molecules by Aggregation of Nanoparticles -- 7.7.2 Chiral Recognition in Aggregation of Helicene‐Grafted Gold Nanoparticles -- 7.7.3 Optical Resolution Using Helicene‐Grafted Silica Nanoparticles -- 7.7.4 Molecular Recognition and Separation of Small Molecules from Metal‐Catalyzed Chemical Equilibrium -- 7.7.5 Molecular Recognition and Separation of Homo‐ and Hetero‐double‐helix Complexes by Helicene‐Grafted Silica Nanoparticles -- 7.7.6 Time Event by Helicene‐Grafted Silica Nanoparticles -- 7.8 Conclusion -- Acknowledgment -- References -- Chapter 8 Multihelicenic Platforms from Halogenated Helicenes and Related Precursors -- 8.1 Introduction -- 8.2 General Synthetic Strategies for Constructing Multihelicenic Platforms from Aromatic Halides -- 8.3 Palladium‐Mediated Cross‐Coupling Reactions Involving Aromatic Halides -- 8.4 Electrophilic Aromatic Substitutions Involving Aromatic Halides -- 8.5 Metal‐Catalyzed Homocouplings with Aromatic Halides -- 8.6 Conclusion. ; References -- Chapter 9 Helical Nanographenes: Synthetic and Chiroptical Achievements -- 9.1 Introduction -- 9.2 All Carbon Helical Nanographenes -- 9.2.1 Achiral or Racemic Helical Nanographenes -- 9.2.2 Chiral and Enantioenriched Helical Nanographenes -- 9.3 Heteroatom‐Containing Helical Nanographenes -- 9.3.1 Helical Nanographenes Containing Heteroatoms of Group 15 (N, P) -- 9.3.2 Helical Nanographenes Containing Heteroatoms of Group 16 (O, S) -- 9.4 Summary Table -- Acknowledgments -- References -- Chapter 10 Helicene‐based Electron Acceptors -- 10.1 Introduction -- 10.2 Helicenes with Remote Electron‐withdrawing Functionalities -- 10.3 Electron‐accepting Heterohelicenes -- 10.3.1 Azahelicenes -- 10.3.2 Incorporation of Oxygen Atoms in Helicenes -- 10.3.3 Borahelicenes -- 10.3.4 Cationic Heterohelicenes -- 10.4 Electron‐accepting π‐extended Frameworks Embedded with Helicenes -- 10.4.1 Extended Helicenes with Naphthalimide Units -- 10.4.2 Perylene Diimide (PDI)‐based Helicenes -- 10.4.3 Terrylene‐based Helicenes -- 10.5 Conclusion and Outlook -- References -- Chapter 11 Chiroptical Properties of Helicenes -- 11.1 Introduction -- 11.2 Chiroptical Spectroscopies of Model Hexahelicenes: A Brief History -- 11.3 Helical Length Dependence of Chiroptical Properties of Helicenes -- 11.4 Impact of Symmetry in Multiple Helicenes on Their Chiroptical Properties -- 11.5 Relevance of Substituents, of Vibronic Couplings, and of Charge Transfer Effects in the ECD Spectra of Helicene Systems -- 11.6 Concluding Remarks -- References -- Chapter 12 Photophysical and Chiroptical Properties of Metal-Organic Helicenic Systems: Experiment vs. Theory -- 12.1 General Aspects -- 12.1.1 Introduction -- 12.1.2 Theory Developments in the Context of Helicene Optical Activity -- 12.2 Case Studies -- 12.2.1 Azahelicene‐Phosphole Pd(II) and Cu(I) Complexes: OR and ECD Analyses. ; 12.2.1.1 Complexes with Extended π‐Conjugated Helicenic P,N Bidentate Ligands.
• Titolo autorizzato: Helicenes
• ISBN: 3-527-82941-5; 3-527-82939-3
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Lingua di pubblicazione: Inglese
• Record Nr.: 9910830677303321
• Lo trovi qui: Univ. Federico II