Molecular Nanographenes : Synthesis, Properties, and Applications (1. Auflage. 2025. 544 S. 1 Tabellen. 244 mm)

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Molecular Nanographenes : Synthesis, Properties, and Applications (1. Auflage. 2025. 544 S. 1 Tabellen. 244 mm)

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  • 製本 Hardcover:ハードカバー版/ページ数 426 p.
  • 言語 ENG
  • 商品コード 9783527353224

Full Description

Explore the world's most powerful materials with nanographene research

Graphene, comprised of a single layer of carbon atoms in a honeycomb nanostructural arrangement, is the thinnest and strongest material yet known to science. Despite that this pristine carbon allotrope exhibits a variety of outstanding properties, its zero bandgap prevents its use for some optoelectronic applications. Fragments of graphene, or nanographenes, have shown a great potential to obviate these problems, thus paving the way for the development of chiroptical and optoelectronic properties.

Molecular Nanographenes constitutes a comprehensive overview on the synthesis of these materials and their properties. Covering their widely varying morphologies, their potential applications, and their valuable chiroptical and photophysical features, it also analyzes multiple approaches to obtain nanographene by using both top-down and bottom-up methodologies. The result is a one-stop shop for materials scientists and other researchers interested in these emergent and fascinating materials.

Molecular Nanographenes readers will also find:

A careful distinction between top-down and bottom-up approaches to nanographene synthesis
Detailed discussion of nanographene configurations including planar, bilayer, helical, nanobelt, and many other geometries
An authorial team with pioneering research experience in the study of nano-sized graphenes and their synthesis

Molecular Nanographenes is ideal for materials scientists, polymer chemists, solid state chemists, organic chemists, and any other researchers looking to work with shape and size-controlled flakes of graphenes.

Contents

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 (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 Čavlović, 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 Materials 391

17.3.1 Preparation 391

17.3.2 Chiral Amplification 392

17.4 Future Directions 393

References 393

18 Nanographene Diradicals 397
Fabrizia Negri and Juan Casado

18.1 Introduction 397

18.2 On the Origin of the Diradical State in Monocyclic Conjugated Hydrocarbons: The Case of Cyclobutadiene 400

18.3 Nanographene Diradical Made from Mixtures of Quinoidal Bonding States and Nonbonding States 403

18.3.1 The Zethrene Family 404

18.3.2 The Bisphenalenylene Family 406

18.3.3 On-Surface Diradicals 407

18.3.4 Graphene Nanoribbons and Their Diradical (i.e. Polyradical Character) 409

18.4 The Diradical State in All-Zig-zag Polycyclic Conjugated Hydrocarbons: On the Reversed Aromatic→Quinoidal Way to Open-Shell Nanographenes 410

18.4.1 The Acenoacene Family 411

18.4.2 The Oligorylene Family 413

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 415

18.5.1 The Peri-Acene Family 415

18.5.2 The Circumacene Family 417

18.5.3 The Unique Case of Rhombenes 419

18.6 Conclusions 420

Acknowledgments 420

References 420

19 Circularly Polarized Luminescence (CPL) in Nanographenes 425
Carlos M. Cruz, Sandra Míguez-Lago, Daniel Salvador-Gil, and Araceli G. Campaña

19.1 Introduction 425

19.2 (1 x HBC)-Based Chiral Nanographenes 428

19.3 (1 x HBC)-Based Heteroatom-Doped Chiral Nanographenes 431

19.4 2 x HBC-Based Chiral Nanographenes 434

19.5 3 x HBC-based Chiral Nanographenes 436

19.6 4 x HBCs-based Chiral Nanographenes and Beyond 438

19.7 Summary Table and Outlook 439

Acknowledgments 445

References 445

20 Redox Properties of Nanographenes 449
Yikun Zhu and Marina A. Petrukhina

20.1 Introduction 449

20.2 Planar Nanographene Fragments 452

20.3 Contorted Nanographenes with Positive and Negative Curvatures 456

20.3.1 Corannulene-based Nanographenes 457

20.3.2 Cyclooctatetraene-based Nanographenes 463

20.3.3 Bilayer Nanographene 468

Acknowledgments 470

References 470

21 Kekulé and Non-Kekulé Nanographenes: A Magnetic Perspective 483
Fupeng Wu, Muhammad Imran, Ji Ma, and Xinliang Feng

21.1 Introduction 483

21.2 Stable Open-Shell Kekulé NGs (S = 0) as Quantum Units 485

21.3 Concealed Non-Kekulé Nanographenes (S = 0) 486

21.4 Obvious Non-Kekulé Nanographenes (S > 0) 488

21.4.1 Spin 1 / 2 Non-Kekulé Nanographenes (S = 1 / 2) 489

21.4.2 High-Spin Non-Kekulé Nanographenes (S ≥ 1) 492

21.5 Engineering of Magnetic Coupling in Non-Kekulé Nanographenes 498

21.5.1 Spin 1 / 2 Dimers 498

21.5.2 Triangulene (S = 1) Dimers and Trimers 501

21.5.3 [3]Triangulene (S = 1) Based Spin Chains 501

21.6 Summary and Outlook 504

Acknowledgments 505

References 505

Index 511

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