Molecular Nanographenes : Synthesis, Properties, and Applications

• Autore: Martin Nazario
• Pubblicazione: Newark : , : John Wiley & Sons, Incorporated, , 2025; ©2025
• Edizione: 1st ed.
• Descrizione fisica: 1 online resource (545 pages)
• Disciplina: 620.115
• Altri autori: NuckollsColin P
• Nota di contenuto: Cover -- Title Page -- Copyright -- Contents -- Foreword -- Preface -- Chapter 1 Aromaticity and Antiaromaticity in Nanographenes: An Overview -- 1.1 Introduction -- 1.2 Global and Local Aromaticity -- 1.3 Methods to Quantify Aromaticity -- 1.3.1 Energetic Descriptors of Aromaticity -- 1.3.2 Electronic Descriptors of Aromaticity -- 1.3.3 Geometric Descriptors of Aromaticity -- 1.3.4 Magnetic Descriptors of Aromaticity -- 1.4 The Analysis of Aromaticity in Nanographene Systems -- 1.5 Concluding Remarks -- Acknowledgments -- References -- Chapter 2 Covalent Patterned Functionalization of Graphene -- 2.1 Introduction -- 2.2 Substrate‐Mediated Chemical Patterning -- 2.3 Tip‐Induced Patterned Functionalization -- 2.4 Lithography‐assisted Molecular Engineering -- 2.5 Laser Writing -- 2.6 Conclusion -- References -- Chapter 3 Nanographenes by Bottom‐up Approach: The Scholl Reaction -- 3.1 Introduction -- 3.2 Planar Nanographenes -- 3.3 Heterocyclic Analogs of Planar Nanographenes -- 3.4 Nonplanar, Curved, and Twisted Nanographenes -- 3.5 Heterocyclic Analogs of Nonplanar Nanographenes -- 3.6 Surface‐assisted (cyclo)Dehydration -- 3.7 Summary and Outlook -- Acknowledgment -- References -- Chapter 4 Racemization Barriers in Chiral Molecular Nanographenes -- 4.1 Introduction -- 4.2 Structural Motifs for Chirality in Nanographenes -- 4.2.1 Gaussian Curvature -- 4.2.2 Helicenes -- 4.2.3 Rolling -- 4.2.4 Strain -- 4.3 Classification of Chiral Molecular NGs According to Their Isomerization Barriers -- 4.4 Flexible Nanographenes (< -- 5 kcal mol−1) -- 4.5 Nanographenes with Spectroscopically Detectable Chirality (5-20 kcal mol−1) -- 4.6 Isolable Nanographenes (20-35 kcal mol−1) -- 4.7 Rigid Nanographenes (> -- 35 kcal mol−1) -- 4.8 Enantioselective Synthesis of Rigid Molecular Nanographenes -- 4.9 Conclusion -- References -- Chapter 5 Synthesis of Helicenes. ; 5.1 Introduction -- 5.2 Characteristics of Helicenes -- 5.3 Synthetic Methodologies -- 5.3.1 Photocyclodehydrogenation of 1,2‐Diaryl Olefins or Arenes -- 5.3.2 Oxidative Aromatic Coupling: Scholl Reaction -- 5.3.3 Transition Metal‐Catalyzed [2 + 2 + 2] Cycloisomerization of π‐Electron Systems -- 5.3.4 Diels-Alder Cycloaddition of Aromatic Vinylethers with p‐Benzoquinone -- 5.3.5 Transition Metal‐Catalyzed Hydroarylation of Alkynes -- 5.3.6 Other Synthetic Approaches -- 5.4 Advanced Helicene Architectures -- 5.5 Summary and Outlook -- Acknowledgment -- References -- Chapter 6 Carbon Nanobelt History and Chemistry -- 6.1 Introduction -- 6.2 Synthetic Attempts to CNBs -- 6.2.1 Some Synthetic Attempts to Cyclacenes -- 6.2.2 CNBs Observed by Mass Spectroscopy -- 6.2.3 Top‐Down Approach to CNBs -- 6.3 Synthesis of CNBs -- 6.4 Synthesis of Related Aromatic Nanobelts -- 6.5 Synthesis of Topological Aromatic Nanobelts -- 6.6 Conclusion -- References -- Chapter 7 Negatively Curved Nanographenes -- 7.1 Introduction -- 7.2 Negatively Curved Nanographenes Containing Seven‐Membered Rings -- 7.2.1 Incorporation of Seven‐Membered Rings at an Early Stage of Synthesis -- 7.2.2 Formation of Seven‐Membered Rings at a Late Stage of the Synthesis -- 7.3 Negatively Curved Nanographenes Containing Eight‐Membered Rings -- 7.3.1 Incorporation of Eight‐Membered Rings at an Early Synthetic Stage -- 7.3.2 Formation of Eight‐Membered Rings at the Final Step of Synthesis -- 7.4 Structures and Stereochemical Dynamics and Properties -- 7.5 Negatively Curved Molecular Nanocarbons Beyond Nanographenes and Bottom‐up Approaches to Carbon Schwarzites -- 7.6 Conclusion and Outlook -- References -- Chapter 8 From PAH‐based Cyclophanes to Nanographenophanes -- 8.1 Introduction -- 8.2 Synthetic Considerations -- 8.3 Pentacenophanes (C22) -- 8.4 Indeno[2,3‐b]triphenylenophanes (C25). ; 8.5 Dibenzo[c,l]chrysenophanes (C26) -- 8.6 Dibenzo[f,j]picenophanes (C30) and Tetrabenz[a,c,h,j]anthracenes (C30) -- 8.7 Teropyrenophanes (C36) -- 8.8 A π‐Extended Azacorannulenophane (C36N) -- 8.9 Hexabenzocoronenophanes (C42) -- 8.10 hept‐Hexabenzocoronenophanes (C43) -- 8.11 Summary and Outlook -- References -- Chapter 9 Bilayer and Multilayer Nanographenes: Synthesis and Properties -- 9.1 Introduction -- 9.2 Van der Waals Molecular Nanographenes -- 9.3 Bilayers from Fused Radicals -- 9.4 Covalently Linked Bilayers -- 9.5 Conclusions -- References -- Chapter 10 Large π‐Extended Carbon Nanorings: From Syntheses to Properties -- 10.1 Introduction -- 10.1.1 Carbon Nanorings with Inserted Six‐Membered Ring‐Based PAHs -- 10.1.1.1 With Inserted Naphthalene(s) -- 10.1.1.2 With Inserted Anthracene(s) or Phenanthrene(s) -- 10.1.1.3 With Inserted Pyrene(s) or Perylene(s) -- 10.1.1.4 With Inserted Other PAHs -- 10.1.2 Carbon Nanorings Consisting Solely of PAHs -- 10.1.2.1 Consisting Solely of Naphthalenes -- 10.1.2.2 Consisting Solely of Anthracenes, Pyrenes, or Chrysenes -- 10.1.2.3 Consisting Solely of Other PAHs -- 10.1.3 CPP‐based Oligomers and Polymers -- 10.1.4 Conclusions and Outlook -- References -- Chapter 11 Nanographenes with Multiple Zigzag Edges -- 11.1 Introduction -- 11.2 Peri‐Acenes -- 11.3 Triangular Nanographenes -- 11.4 Peri‐acenoacenes -- 11.5 Circumarenes -- 11.6 Conclusion -- References -- Chapter 12 Synthesis of Graphene Nanoribbons, Nanographenes, and Fused Aromatic Networks Through the Formation of Pyrazine Rings -- 12.1 Introduction -- 12.2 Graphene Nanoribbons and Nanographenes -- 12.3 Fused Aromatic Networks -- 12.4 Conclusions -- References -- Chapter 13 Conjugated Nanohoops: Synthesis, Properties, and Applications -- 13.1 Introduction -- 13.2 Synthetic Strategies to Conjugated Nanohoops. ; 13.2.1 Pt‐, Ni‐, or Au‐Mediated Macrocyclizations in the Synthesis of Nanohoops -- 13.2.2 Synthesis of Conjugated Nanohoops via Kinked Precursors to π‐System Panels -- 13.3 Properties of Conjugated Nanohoops -- 13.3.1 Optoelectronic Properties -- 13.3.2 Chirality -- 13.3.3 Host-Guest Chemistry -- 13.3.4 Solid‐State Structures -- 13.4 Applications of Conjugated Nanohoops -- 13.4.1 Organic Electronics -- 13.4.2 Bottom‐up Synthesis of Carbon Nanotubes -- 13.4.3 Biological Fluorophores -- 13.5 Conclusions -- References -- Chapter 14 Chiral Polycyclic Aromatic Compounds with Monkey Saddle Topologies -- 14.1 Introduction -- 14.2 Saddle Mathematics -- 14.3 Synthesis -- 14.4 X‐Ray Crystal Structures of Monkey Saddle PAHs -- 14.5 NICS and ACID Plots -- 14.6 Inversion Barriers and Chiroptical Properties -- 14.7 Other Monkey Saddle PAHs and Related Systems -- 14.8 Summary and Outlook -- References -- Chapter 15 On‐Surface Synthesis of π‐Conjugated Polymers -- 15.1 Introduction -- 15.2 Content -- 15.3 Conclusions -- References -- Chapter 16 Merging Organic Chemistry with Surface Science for the Preparation of Nanographenes -- 16.1 Introduction -- 16.2 Scanning Probe Microscopies for the Characterization of Nanographenes Obtained by Solution‐Phase Chemistry -- 16.3 Combining Solution‐Phase and On‐Surface Chemistry for the Synthesis of Nanographenes -- 16.3.1 Surface‐Assisted Cyclodehydrogenation Reaction -- 16.3.2 Surface‐Assisted Ullmann‐Type Reactions -- 16.3.3 Alternative Reactions Used for the On‐Surface Preparation of Nanographenes -- 16.3.4 Combining On‐Surface Reactions Toward the Preparation of Nanographenes -- 16.4 Concluding Remarks -- References -- Chapter 17 Chiral Materials from Twistacenes and Helicenes -- 17.1 Introduction -- 17.1.1 Background -- 17.1.2 The Building Block -- 17.2 Twistacene‐based Materials -- 17.2.1 Preparation -- 17.2.2 Properties. ; 17.2.3 Organic Photovoltaics and Photodetectors -- 17.2.4 Electrochemical Storage Using hPDIs -- 17.3 Helicene‐Based Materials -- 17.3.1 Preparation -- 17.3.2 Chiral Amplification -- 17.4 Future Directions -- References -- Chapter 18 Nanographene Diradicals -- 18.1 Introduction -- 18.2 On the Origin of the Diradical State in Monocyclic Conjugated Hydrocarbons: The Case of Cyclobutadiene -- 18.3 Nanographene Diradical Made from Mixtures of Quinoidal Bonding States and Nonbonding States -- 18.3.1 The Zethrene Family -- 18.3.2 The Bisphenalenylene Family -- 18.3.3 On‐Surface Diradicals -- 18.3.4 Graphene Nanoribbons and Their Diradical (i.e. Polyradical Character) -- 18.4 The Diradical State in All‐Zig‐zag Polycyclic Conjugated Hydrocarbons: On the Reversed Aromatic→Quinoidal Way to Open‐Shell Nanographenes -- 18.4.1 The Acenoacene Family -- 18.4.2 The Oligorylene Family -- 18.5 The Diradical State as a Result of Zig‐zag Versus Arm‐chair Structures with "Mobile" Quinoidal Rings with Quinoidal → Aromatic Transformation in the Diradical State -- 18.5.1 The Peri‐Acene Family -- 18.5.2 The Circumacene Family -- 18.5.3 The Unique Case of Rhombenes -- 18.6 Conclusions -- Acknowledgments -- References -- Chapter 19 Circularly Polarized Luminescence (CPL) in Nanographenes -- 19.1 Introduction -- 19.2 (1 × HBC)‐Based Chiral Nanographenes -- 19.3 (1 × HBC)‐Based Heteroatom‐Doped Chiral Nanographenes -- 19.4 2 × HBC‐Based Chiral Nanographenes -- 19.5 3 × HBC‐based Chiral Nanographenes -- 19.6 4 × HBCs‐based Chiral Nanographenes and Beyond -- 19.7 Summary Table and Outlook -- Acknowledgments -- References -- Chapter 20 Redox Properties of Nanographenes -- 20.1 Introduction -- 20.2 Planar Nanographene Fragments -- 20.3 Contorted Nanographenes with Positive and Negative Curvatures -- 20.3.1 Corannulene‐based Nanographenes. ; 20.3.2 Cyclooctatetraene‐based Nanographenes.
• Titolo autorizzato: Molecular Nanographenes
• ISBN: 9783527845002; 3527845003; 9783527845019; 3527845011; 9783527844999; 3527844996
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Lingua di pubblicazione: Inglese
• Record Nr.: 9911020235303321
• Lo trovi qui: Univ. Federico II