174 Index. E Electronic chemistry (EC), 70 Enediyne (EDY), Bergman cyclization. See Bergman cyclization, EDY
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1 Index A Anthracene-bridged biphenalenyl, Antiferromagnetic NGs, 9 Armchair-edged graphene nanoribbons (AGNRs), 2, 3, 36 molecular precursors, solution-mediated methods, Armchair-edged nanographenes (A-NGs), 4, 7 Azide alkyne cycloaddition, B B-7-armchair-edged graphene nanoribbons (B-7-AGNRs), 55 1,4-Benzenediboronic acid (BDBA), 75, 76 Bergman cyclization, EDY carbon nanomembranes EDY SAMs, formation of, 161, 162 ordered porous CNMs, 161, 163 plate-like CNMs, 161, 163 supercapacitors, SS-CNMs (see Supercapacitors, SS-CNMs) tubular carbon monolayers, SAED pattern of, 161, 162 tubular CNMs, 161, 162 carbon-rich nanoparticles, C-dots, PL mechanism of, methyl methacrylate, 155 quantum dots, SCNP, conjugated microporous polymers, BODA monomers, glassy carbons, HET, 160, 161 DNHD, homopolymerization of, 85, limitations, 152 mechanism for, polyarylenes, homopolymerization of, 150, 151 vinyl monomers, polymerization of, 150, 151 6,6 0 -Bipentacene, Bisanthene, 7, 9 Bis-ortho-diynylarene (BODA), 151, Bispentacenequinone, 12 Bistetracene, 9 10 Bis-zigzag HBC, 4 6 Bottom-up-fabricated GNRs energy band structures, general synthesis scheme, molecular precursors, design of, spatial isolation, of energy states, substitutional doping, Buckybowls on-surface synthesis, 135 structures, C Carbon dots (C-dots), Carbon nanomembranes (CNMs), Bergman cyclization EDY SAMs, formation of, 161, 162 ordered porous CNMs, 161, 163 plate-like CNMs, 161,
2 174 Index Carbon nanomembranes (CNMs) (cont.) supercapacitors, SS-CNMs Co 3 O 4 nanoparticles, electrochemical evaluation of, specific capacitances of, 164, 166 tubular CNMs, tubular carbon monolayers, SAED pattern of, 161, 162 tubular CNMs, 161, 162 tubular SS-CNMs, Carbon nanotubes (CNTs) CVD, 128 seed-templated growth, separation, Carbon quantum dots (CQDs), 156 CeGNRs. See Cove-edge GNRs (CeGNRs) C 60 fullerene cyclodehydrogenation, high-performance liquid chromatography (HPLC) separation, 128 structures, 136 surface-assisted approach, 135 zipping approach, CGNRs. See Chevron GNRs (CGNRs) Chemical vapor deposition (CVD), 128 Chevron GNRs (CGNRs) electronic HREELS spectra, 53 GW approximation, 49 heterojunctions, molecular precursors, nitrogen edge-doping, on-surface polymerization, UPS spectra, 53 Chiral GRNs, 45, 49 Chirality pure SWCNTs, 130, Clar s sextet rule, 7, 9, 11, 18 Click reaction. See Azide alkyne cycloaddition CNTs. See Carbon nanotubes (CNTs) Condensation reaction of boronic acids, Conjugated microporous polymers (CMPs), BODA monomers, glassy carbons, HET, 160, 161 Cove-edged nanographenes (C-NGs), 4 Cove-edge GNRs (CeGNRs), 2, 41, 49 CVD. See Chemical vapor deposition (CVD) Cyclodehydrogenation buckybowl synthesis, C 57 H 33 N 3, Pt(111) surface, 78, 80 DBDA monomers, 104, 105 fullerene synthesis, 137, 138 GNRs, fabrication of, 38, 40, 44, 45, 49, 78, 79 PAHs, peri-fused acenes, 12, 19, 21, 27 segmented GNRs, SWCNTs, Cyclohexa-m-phenylene (CHP), 88 Cyclotrimerization, D Dehydrogenation, 76 77, 89 Density functional theory (DFT) CGNRs, 57, 59 cyclization mechanism, 78 DNHD, Bergman cyclization of, 154 GNRs, fabrication of, 42, 44, 45, 47, 49, 51 peri-fused acenes, 12, 20, 21, 27 photoluminescent C-dots, 157 Ullmann coupling, 73, 74 4,4 0 -Diamino-p-terphenyl (DATP), 85, 86 2,3-Dibromoanthracene (2,3-DBA), ,10-Dibromoanthracene (9,10-DBA), 104, ,10 0 -Dibromo-9,9 0 -bianthryl (DBBA), 78, 79 Dibromodianthracene (DBDA) monomers, 104, 105 Dibromohexabenzocoronene (DBHBC), 109, 110 4,4 00 -Dibromo-p-pterphenyl (Br-(ph) 3 -Br), Diiodohexabenzocoronene (DIHBC), 109 1,6-Di-2-naphthylhex-3-ene-1,5-diyne (DNHD), 85, Donor-acceptor-donor (DAD) monomer, Doped NGs, E Electronic chemistry (EC), 70 Enediyne (EDY), Bergman cyclization. See Bergman cyclization, EDY F Fjord ring closure, 131, Flash vacuum pyrolysis (FVP) approach, , 139 Friedel Crafts alkylation, 18, 164 Fullerenes, 128
3 Index 175 Fully benzenoid HBC, 4 5 FVP approach. See Flash vacuum pyrolysis (FVP) approach G Gel permeation chromatography (GPC), 155 Geodesic PAHs, Glaser coupling reaction, 81, 82 Glaser Hay coupling, 155 GNRs. See Graphene nanoribbons (GNRs) Graphene applications, 34 edge structures, 2 electronic properties, Graphene nanoribbons (GNRs) bottom-up synthesis, 3 energy band structures, general synthesis scheme, molecular precursors, design of, spatial isolation, of energy states, substitutional doping, cyclodehydrogenation, 78, 79 electronic properties, 36 top-down synthesis, 3 lithography, oxygen plasma etching, 37 unzipping process, types, 2 zigzag-edge structures, Graphene quantum dots (GQDs), 26 L Lithography, Local density of states (LDOS) maps, Lowest unoccupied molecular orbital (LUMO), 6, 7, 9, , 157 M Mallory s photocyclization method, 133 Methyl methacrylate (MMA), 155 Mono-zigzag HBC, 4 6 Monte Carlo simulations, 108 Multistep organic synthesis, 131 N Nanographenes (NGs), 3, 128 doping, Nanoribbons, 128. See also Graphene nanoribbons (GNRs) Nanotubes. See also Single-walled carbon nanotubes (SWCNTs) structures, 128 Naphthalene-bridged biphenalenyl, NGs. See Nanographenes (NGs) Nitrogen-boron-nitrogen (NBN)-edged NGs, Nitrogen-doped CGNRs DFT calculations, 57 edge reconstruction, H HBC-derived NGs, 4 7 Heptazethrene, Hexabenzocoronene (HBC), ,3,6,7,10,11-Hexaethynyltriphenylene (HET), 160, 161 2,3,6,7,10,11-Hexahydroxytriphenylene (HHTP), 76 Hexa-peri-hexabenzocoronene (HBC), 3, 27 Highest occupied molecular orbital (HOMO), 6, 7, 9, , 157 Hydrogen-terminated GNRs, 46 I Intramolecular aryl aryl domino-coupling, Isolated pentagon rule (IPR), O Octazethrene, On-surface polymerization chevron-shaped GNRs, Cu(111), Ag(111), and Au(111) surfaces, DAD monomers and DAD n oligomers, ,10-DBA, 104, 106 2,3-DBA oligomerization, Au(111) and Au(100) surfaces, DBDA monomers, 104, 105 DBHBC oligomerization, Au(111) and Cu(111) surfaces, 109, 110 HBC, metal-carbon bonds, molecular wires, conductance of inverse decay lengths,
4 176 Index On-surface polymerization (cont.) poly(9,9-dimethylfluorene) chain, 115, 116 single molecule, conductance of, poly(meta-phenylene), 103 poly(para-phenylene), 103 polyarylene precursor, formation of, , 107 principle, 102 STM-tip-induced activation, 101, 102 1,4,5,8-tetrabromonaphthalene, 103, 104 two-dimensional networks, Au(111) surface temperature, influence of, 120, 121 porphyrin networks, sequential activation technique, 122, 123 zig-zag edge GNRs, cyclodehydrogenation, 105, 107 Oxygen-boron-oxygen (OBO)-doped peri-tetracenes, 19 21, 27 Oxygen plasma etching, 37 P PAHs. See Polycyclic aromatic hydrocarbons (PAHs) Palladium nanoparticle-loaded carbon nanomembranes (Pd@SS-CNMs), Peri-acene-derived NGs, 7 14 Peri-pentacene, Peri-pentacenetetraketone, 13 Peri-tetracene chemical structures, 8, 11, 20 OBO-doped, 19, 21, 27 Perylene, 7 3,4,9,10-Perylenetetracarboxylic-dianhydride (PTCDA), 85, 86 Phenalenyl-derived NGs, Phenyl-bridged biphenalenyl, Planar PAHs, 133 Poly(meta-phenylene) (PMP), 103 Poly(methyl acrylate) (PMA), 156 Poly(para-phenylene) (PPP), 103 Polycyclic aromatic hydrocarbons (PAHs), 3 surface-assisted synthesis, zipping approach, 130, 133 Polynaphthalenes (PNs), 151, 152 Polyphenylenes, Poly( p-phenylene)s (PPPs), 151 Pre-fused dibenzo[a,m]rubicene, 11 Protopolymers, 103 Q Quantum dots (QDs), Quateranthene, 8 9 R Reversible addition fragmentation chain transfer (RAFT) polymerization, 151 S SAMs. See Self-assembly monolayers (SAMs) S-13-armchair-edged graphene nanoribbons (S-13-AGNRs), 54 Scanning tunneling microscopy (STM), 37, 101 AGNRs, 47, 48, 55, 59, 61 azide alkyne cycloaddition reaction, CGNRs, 57, 58 cyclodehydrogenation C 57 H 33 N 3, Pt(111) surface, 78, 80 GNRs, fabrication of, 78, 79 DATP, PTCDA and TAPT, 85, 86 peri-pentacene, 13, 14 TAPB, TEB and Ext-TEB, Ag(111) surface, 81, 82 Ullmann coupling reaction biphenyl, synthesis of, 71 brominated porphyrin-derived molecules, kinds of, 72 Br-(ph) 3 -Br, Cu(111) surface, hexaiodo-substituted macrocycle CHP, 88 molecular wires, fabrication of, 74 TBB, Ag(111) and Ag(110) surfaces, 89 TBN molecules deposition, Au(111) surface, 89 ZGNRs, Schiff base reactions, 74 75, 91 Scholl reaction, 104, 133 SCMPs. See Soluble conjugated microporous polymers (SCMPs) SCNPs. See Single-chain polymer nanoparticles (SCNPs) SCOFs. See Surface covalent organic frameworks (SCOFs) Segmented GNRs, Selected area electron diffraction (SAED), 161, 162 Self-assembly monolayers (SAMs), 68 69, 161, armchair graphene nanoribbons (7-AGNRs), 36
5 Index 177 boron doping, 52, heterojunctions, 57, graphene nanoribbons (7 GNRs) electronic structure, 110 inverse decay lengths, Silica-supported carbon nanomembranes (SS-CNMs) Co 3 O 4 nanoparticles, electrochemical evaluation of, specific capacitances of, 164, 166 tubular CNMs, Single-chain polymer nanoparticles (SCNPs), Single-walled carbon nanotubes (SWCNTs) fractionalization, 130 surface-assisted synthesis, top-down approaches, 37 6-zigzag-edged GNRs (6-ZGNRs) bottom-up synthesis, solution-mediated fabrication, 28 spin-polarized edge states, synthesis and characterization, Soluble conjugated microporous polymers (SCMPs), Sonogashira coupling reactions, 81, 83, 161 SS-CNMs. See Silica-supported carbon nanomembranes (SS-CNMs) Supercapacitors, SS-CNMs Co 3 O 4 nanoparticles, electrochemical evaluation of, specific capacitances of, 164, 166 tubular CNMs, Super-heptazethrene absorption spectra, synthesis, 18 Surface-assisted reactions advantages, challenges, covalently bonded 2D structures, 68 definition, 68 EC conditions, 70 synthesis buckybowl, fullerenes, SWCNTs, ultrahigh vacuum conditions advantages, azide-alkyne cycloaddition, Bergman cyclization, 85 challenges, 70 condensation of boronic acids, conjugated 1D/2D organic materials, fabrication of, cyclodehydrogenation, cyclotrimerization, DATP, PTCDA and TAPT, 85, 86 dehydrogenation, 76 77, 89 Glaser coupling, 81, 82 Schiff base reactions, Sonogashira coupling reaction, 81, 83 Ullmann coupling (see Ullmann coupling reaction) Surface covalent organic frameworks (SCOFs), 75 76, 85 87, 90, 91 Suzuki cross-coupling reaction, 6, 21, 25, 166 SWCNTs. See Single-walled carbon nanotubes (SWCNTs) T Teranthene, 8 9 Tetraaryl-substituted fused bispentacenequinone, 12 1,4,5,8-Tetrabromonaphthalene (TBN), 89, 103, 104 1,2,4,5-Tetracyanobenzene (TCNB), 190 Tetra( p-bromophenyl)-quaterphenyl (TBQ), 120 Tetra-zigzag HBC, Armchair graphene nanoribbons (13-AGNRs) heterojunctions, 57, precursors, 42 sulfur edge-doping, Top-down-fabricated GNRs lithography, oxygen plasma etching, 37 unzipping process, ,3,5-Tri(4-hydroxyphenyl)benzene (TPB), 85 1,3,5-Triethynyl-benzene (TEB), 81, 82 1,3,5-Tris(4-acetylphenyl)benzene (TAPB), ,3,5-Tris(4-bromophenyl)benzene (TBB), 89 1,3,5-Tris-(4-ethynylphenyl)benzene (Ext-TEB), 81, 82 2,4,6-Tris(4-aminophenyl)-1,3,5-triazine (TAPT), 85, 86 Tri-zigzag HBC, 4 6 Two-dimensional networks (2D networks),
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