Foreword xiii Preface xvii 1 Aromaticity and Antiaromaticity in Nanographenes: An Overview 1 Albert Artigas and Miquel Solà 1.1 Introduction 1 1.2 Global and Local Aromaticity 2 1.3 Methods to Quantify Aromaticity 6 1.3.1 Energetic Descriptors of Aromaticity 7 1.3.2 Electronic Descriptors of Aromaticity 9 1.

3.3 Geometric Descriptors of Aromaticity 13 1.3.4 Magnetic Descriptors of Aromaticity 14 1.4 The Analysis of Aromaticity in Nanographene Systems 20 1.5 Concluding Remarks 23 Acknowledgments 24 References 24 2 Covalent Patterned Functionalization of Graphene 31 Tao Wei and Andreas Hirsch 2.1 Introduction 31 2.2 Substrate-Mediated Chemical Patterning 33 2.

3 Tip-Induced Patterned Functionalization 35 2.4 Lithography-assisted Molecular Engineering 37 2.5 Laser Writing 44 2.6 Conclusion 50 References 51 3 Nanographenes by Bottom-up Approach: The Scholl Reaction 55 Daniel T. Gryko, Wojciech D. Petrykowski, and Krzysztof J. Kochanowski 3.1 Introduction 55 3.

2 Planar Nanographenes 56 3.3 Heterocyclic Analogs of Planar Nanographenes 63 3.4 Nonplanar, Curved, and Twisted Nanographenes 66 3.5 Heterocyclic Analogs of Nonplanar Nanographenes 71 3.6 Surface-assisted (cyclo)Dehydration 74 3.7 Summary and Outlook 76 Acknowledgment 77 References 77 4 Racemization Barriers in Chiral Molecular Nanographenes 83 Jesús M. Fernández-García, Patricia Izquierdo-García, Salvatore Filippone, and Nazario Martín 4.1 Introduction 83 4.

2 Structural Motifs for Chirality in Nanographenes 84 4.2.1 Gaussian Curvature 85 4.2.2 Helicenes 85 4.2.3 Rolling 86 4.2.

4 Strain 87 4.3 Classification of Chiral Molecular NGs According to Their Isomerization Barriers 87 4.4 Flexible Nanographenes ( 4.5 Nanographenes with Spectroscopically Detectable Chirality (5-20 kcal mol −1) 89 4.6 Isolable Nanographenes (20-35 kcal mol −1) 90 4.7 Rigid Nanographenes (>35 kcal mol −1) 93 4.8 Enantioselective Synthesis of Rigid Molecular Nanographenes 95 4.9 Conclusion 98 References 99 5 Synthesis of Helicenes 105 Irena G.

Stará and Ivo Starý 5.1 Introduction 105 5.2 Characteristics of Helicenes 106 5.3 Synthetic Methodologies 107 5.3.1 Photocyclodehydrogenation of 1,2-Diaryl Olefins or Arenes 107 5.3.2 Oxidative Aromatic Coupling: Scholl Reaction 111 5.

3.3 Transition Metal-Catalyzed [2 + 2 + 2] Cycloisomerization of π-Electron Systems 111 5.3.4 Diels-Alder Cycloaddition of Aromatic Vinylethers with p-Benzoquinone 117 5.3.5 Transition Metal-Catalyzed Hydroarylation of Alkynes 119 5.3.6 Other Synthetic Approaches 120 5.

4 Advanced Helicene Architectures 123 5.5 Summary and Outlook 137 Acknowledgment 137 References 137 6 Carbon Nanobelt History and Chemistry 149 Hiroki Shudo, Daiki Imoto, Akiko Yagi, and Kenichiro Itami 6.1 Introduction 149 6.2 Synthetic Attempts to CNBs 151 6.2.1 Some Synthetic Attempts to Cyclacenes 151 6.2.2 CNBs Observed by Mass Spectroscopy 152 6.

2.3 Top-Down Approach to CNBs 152 6.3 Synthesis of CNBs 153 6.4 Synthesis of Related Aromatic Nanobelts 154 6.5 Synthesis of Topological Aromatic Nanobelts 157 6.6 Conclusion 159 References 159 7 Negatively Curved Nanographenes 163 Ka Man Cheung and Qian Miao 7.1 Introduction 163 7.2 Negatively Curved Nanographenes Containing Seven-Membered Rings 164 7.

2.1 Incorporation of Seven-Membered Rings at an Early Stage of Synthesis 165 7.2.2 Formation of Seven-Membered Rings at a Late Stage of the Synthesis 168 7.3 Negatively Curved Nanographenes Containing Eight-Membered Rings 174 7.3.1 Incorporation of Eight-Membered Rings at an Early Synthetic Stage 175 7.3.

2 Formation of Eight-Membered Rings at the Final Step of Synthesis 179 7.4 Structures and Stereochemical Dynamics and Properties 181 7.5 Negatively Curved Molecular Nanocarbons Beyond Nanographenes and Bottom-up Approaches to Carbon Schwarzites 184 7.6 Conclusion and Outlook 186 References 188 8 From PAH-based Cyclophanes to Nanographenophanes 193 Parinaz Salari and Graham J. Bodwell 8.1 Introduction 193 8.2 Synthetic Considerations 197 8.3 Pentacenophanes (C22) 199 8.

4 Indeno[2,3-b]triphenylenophanes (C25) 201 8.5 Dibenzo[c,l]chrysenophanes (C26) 203 8.6 Dibenzo[f,j]picenophanes (C30) and Tetrabenz[a,c,h,j]anthracenes (c30) 205 8.7 Teropyrenophanes (C36) 207 8.8 A π-Extended Azacorannulenophane (C36 N) 211 8.9 Hexabenzocoronenophanes (C42) 213 8.10 hept-Hexabenzocoronenophanes (C43) 217 8.11 Summary and Outlook 218 References 219 9 Bilayer and Multilayer Nanographenes: Synthesis and Properties 223 Patricia Izquierdo-García, Juan Lión-Villar, Jesús M.

Fernández-García, and Nazario Martín 9.1 Introduction 223 9.2 Van der Waals Molecular Nanographenes 225 9.3 Bilayers from Fused Radicals 230 9.4 Covalently Linked Bilayers 232 9.5 Conclusions 238 References 239 10 Large π-Extended Carbon Nanorings: From Syntheses to Properties 243 Jinyi Wang, Dapeng Lu, and Pingwu Du 10.1 Introduction 243 10.1.

1 Carbon Nanorings with Inserted Six-Membered Ring-Based PAHs 244 10.1.1.1 With Inserted Naphthalene(s) 244 10.1.1.2 With Inserted Anthracene(s) or Phenanthrene(s) 247 10.1.

1.3 With Inserted Pyrene(s) or Perylene(s) 248 10.1.1.4 With Inserted Other PAHs 249 10.1.2 Carbon Nanorings Consisting Solely of PAHs 252 10.1.

2.1 Consisting Solely of Naphthalenes 253 10.1.2.2 Consisting Solely of Anthracenes, Pyrenes, or Chrysenes 254 10.1.2.3 Consisting Solely of Other PAHs 255 10.

1.3 CPP-based Oligomers and Polymers 258 10.1.4 Conclusions and Outlook 261 References 262 11 Nanographenes with Multiple Zigzag Edges 267 Ya Zou and Jishan Wu 11.1 Introduction 267 11.2 Peri-Acenes 268 11.3 Triangular Nanographenes 275 11.4 Peri-acenoacenes 278 11.

5 Circumarenes 279 11.6 Conclusion 283 References 285 12 Synthesis of Graphene Nanoribbons, Nanographenes, and Fused Aromatic Networks Through the Formation of Pyrazine Rings 289 Felix Hernández-Culebras and Aurelio Mateo-Alonso 12.1 Introduction 289 12.2 Graphene Nanoribbons and Nanographenes 289 12.3 Fused Aromatic Networks 293 12.4 Conclusions 300 References 300 13 Conjugated Nanohoops: Synthesis, Properties, and Applications 303 Birgit Esser, Philipp Seitz, Andrej Weber, and Jan S. Wössner 13.1 Introduction 303 13.

2 Synthetic Strategies to Conjugated Nanohoops 303 13.2.1 Pt-, Ni-, or Au-Mediated Macrocyclizations in the Synthesis of Nanohoops 304 13.2.2 Synthesis of Conjugated Nanohoops via Kinked Precursors to π-System Panels 307 13.3 Properties of Conjugated Nanohoops 309 13.3.1 Optoelectronic Properties 309 13.

3.2 Chirality 311 13.3.3 Host-Guest Chemistry 311 13.3.4 Solid-State Structures 313 13.4 Applications of Conjugated Nanohoops 314 13.4.

1 Organic Electronics 314 13.4.2 Bottom-up Synthesis of Carbon Nanotubes 316 13.4.3 Biological Fluorophores 317 13.5 Conclusions 317 References 318 14 Chiral Polycyclic Aromatic Compounds with Monkey Saddle Topologies 323 Tobias Kirschbaum and Michael Mastalerz 14.1 Introduction 323 14.2 Saddle Mathematics 327 14.

3 Synthesis 328 14.4 X-Ray Crystal Structures of Monkey Saddle PAHs 331 14.5 NICS and ACID Plots 333 14.6 Inversion Barriers and Chiroptical Properties 334 14.7 Other Monkey Saddle PAHs and Related Systems 337 14.8 Summary and Outlook 339 References 340 15 On-Surface Synthesis of π-Conjugated Polymers 345 Nazario Martín and David Écija 15.1 Introduction 345 15.2 Content 345 15.

3 Conclusions 358 References 360 16 Merging Organic Chemistry with Surface Science for the Preparation of Nanographenes 363 Iago Pozo, Dolores Pérez, and Diego Peña 16.1 Introduction 363 16.2 Scanning Probe Microscopies for the Characterization of Nanographenes Obtained by Solution-Phase Chemistry 364 16.3 Combining Solution-Phase and On-Surface Chemistry for the Synthesis of Nanographenes 366 16.3.1 Surface-Assisted Cyclodehydrogenation Reaction 367 16.3.2 Surface-Assisted Ullmann-Type Reactions 369 16.

3.3 Alternative Reactions Used for the On-Surface Preparation of Nanographenes 371 16.3.4 Combining On-Surface Reactions Toward the Preparation of Nanographenes 373 16.4 Concluding Remarks 373 References 375 17 Chiral Materials from Twistacenes and Helicenes 381 Si Tong Bao, Qifeng Jiang, Haoyu Jiang, Daniel Èavloviæ, and Colin Nuckolls 17.1 Introduction 381 17.1.1 Background 381 17.

1.2 The Building Block 381 17.2 Twistacene-based Materials 382 17.2.1 Preparation 382 17.2.2 Properties 383 17.2.

3 Organic Photovoltaics and Photodetectors 388 17.2.4 Electrochemical Storage Using hPDIs 389 17.3 Helicene-Based Mater.