Polycyclic arenes and heteroarenes: synthesis, properties, and applications
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| Format: | Book |
| Language: | English |
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Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
[2016]
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XVI, 337 Seiten Illustrationen, Diagramme |
| ISBN: | 3527338470 9783527338474 9783527689545 |
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| 245 | 1 | 0 | |a Polycyclic arenes and heteroarenes |b synthesis, properties, and applications |c edited by Qian Miao |
| 264 | 1 | |a Weinheim |b Wiley-VCH Verlag GmbH & Co. KGaA |c [2016] | |
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| 653 | |a Halbleiter | ||
| 653 | |a Nanomaterialien | ||
| 653 | |a Nanomaterials | ||
| 653 | |a Nanotechnologie | ||
| 653 | |a Nanotechnology | ||
| 653 | |a Semiconductors | ||
| 653 | |a Supramolecular Chemistry | ||
| 653 | |a Supramolekulare Chemie | ||
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CONTENTS
PREFACE XI
LIST OF CONTRIBUTORS XIII
PART I POLYCYCLIC ARENES 1
1 OPEN-SHELL BENZENOID POLYCYCLIC HYDROCARBONS 3
SOUMYAJIT DAS AND
JISHAN WU
1.1 INTRODUCTION 3
1.2 HIGHER ORDER ACENES 6
1.3 PHENALENYL-BASED DIRADICALOIDS 9
1.3.1 BIS(PHENALENYL)S 10
1.3.2 ZETHRENES 14
1.4 ANTHENES AND PERIACENES 21
1.5 JI-EXTENDED P-QUINODIMETHANE 27
1.6 TRIANGULENE-BASED TRIPLET BIRADICALS 31
1.7 POTENTIAL APPLICATIONS 32
1.8 CONCLUSION 33
REFERENCES 33
2 PLANAR CYDOPENTA-FUSED POLYCYCLIC ARENES 37
GABRIEL E. RUDEBUSCH AND
MICHAEL M. HALEY
2.1 INTRODUCTION 37
2.2 ACENAPHTHYLENES 37
2.3 DIBENZOPENTALENES 43
2.4 INDENOFLUORENES 51
2.5 CONCLUSIONS 57
ACKNOWLEDGMENT 58
REFERENCES 58
3 GROWING BUCKYBOWL CHEMISTRY 61
SHUHEI HIGASHIBAYASHI
AND HIDEHIRO
SAKURAI
3.1 INTRODUCTION 61
3.2 JR-EXTENDED BUCKYBOWLS 62
HTTP://D-NB.INFO/1070857157
VII CONTENTS
3.3 CHIRAL BUCKYBOWL 65
3.4 HETEROBUCKYBOWL
68
3.5 COLUMNAR CRYSTAL PACKING OF BUCKYBOWLS 75
3.6 SUMMARY AND CONCLUSIONS 80
REFERENCES 80
4 POLYCYDIC ARENES CONTAINING SEVEN-MEMBERED CARBOCYCLES 85
KWAN YIN
CHEUNG AND
QIAN MIAO
4.1 INTRODUCTION 85
4.2 AZULENE, OLIGO-AZULENES, AND FUSED AZULENES 85
4.3 POLYCYCLIC ARENES CONTAINING 5H-DIBENZO[A,D]CYCLOHEPTENE
UNITS 92
4.4 CYCLOHEPTA[RFE]NAPHTHALENE, DICYCLOHEPTA[TFE,(/]NAPHTHALENE, AND
THEIR BENZANNULATED DERIVATIVES 97
4.5 CURVED POLYCYCLIC ARENES CONTAINING HIGHLY FUSED
CYCLOHEPTATRIENE 101
4.6 CONCLUSIONS 107
ACKNOWLEDGMENT 107
REFERENCES 107
5 POLYCYCLIC ARENES CONTAINING EIGHT-MEMBERED CARBOCYCLES 111
CHUN-LIN DENG, XIAO-SHUI PENG,
AND HENRY N. C. WONG
5.1 INTRODUCTION 111
5.2 [8]ANNULENES 112
5.2.1 DEHYDRO[8]ANNULENES 112
5.2.2 BENZO-FUSED [8]ANNULENES 116
5.2.3 BIPHENYLENE-FUSED [8]ANNULENES 119
5.3 TETRAPHENYLENES 122
5.3.1 SYNTHESIS 122
5.3.1.1 RING OPENING OF THE STRAINED FOUR-MEMBERED RING OF BIPHENYLENE
DERIVATIVES 123
5.3.1.2 TRANSITION-METAL-MEDIATED OXIDATIVE COUPLING 123
5.3.1.3 CYCLOADDITION-DEOXYGENATION PROTOCOL 124
5.3.1.4 SYNTHESIS OF ENANTIOPURE TETRAPHENYLENES 125
5.3.2 PROPERTIES AND POTENTIAL APPLICATIONS 127
5.4 [8]CIRCULENE 133
5.5 CONCLUDING REMARKS 138
REFERENCES 138
6 CYDOPARAPHENYLENES AND CARBON NANORINGS 143
SHIGERU YAMAGO,
EIICHI KAYAHARA,
AND SIGMA HASHIMOTO
6.1 INTRODUCTION 143
6.2 EARLY DEVELOPMENTS 144
6.3 STRAIN AND HOMO/LUMO ENERGIES OF CPPS 146
CONTENTS VII
6.4 SYNTHESIS OF CPPS 147
6.5 PROPERTIES OF CPPS 154
6.5.1 PHOTOPHYSICAL PROPERTIES 154
6.5.2 REDOX PROPERTIES OF CPPS IS5
6.5.3 HOST-GUEST CHEMISTRY 158
6.6 SUMMARY AND CONCLUSIONS 160
REFERENCES 160
7 ADVANCES IN CHEMISTRY OF DEHYDROBENZOANNULENES 163
SHUNPEI NOBUSUE
AND YOSHITO
TOBE
7.1 INTRODUCTION 163
7.2 SYNTHESIS AND PROPERTIES OF NEW DBAS 164
7.2.1 SINGLE-RING DBAS 164
7.2.2 MULTIPLE-RING DBAS 166
7.3 DBAS AS GRAPHYNE AND GRAPHDIYNE MOTIFS 169
7.3.1 THEORETICAL AND SYNTHETIC STUDIES ON GRAPHYNE AND
GRAPHDIYNE 170
7.3.2 SYNTHESIS OF GRAPHYNE AND GRAPHDIYNE MOTIFS AND RELATED MULTIPLE
DBA SYSTEMS 171
7.4 DBAS AS SUPRAMOLECULAR BUILDING BLOCKS 171
7.4.1 CRYSTAL ENGINEERING 172
7.4.2 3D ASSEMBLIES: GELS, FIBERS, VESICLES, AND LIQUID CRYSTALS 174
7.4.3 2D SELF-ASSEMBLY ON SURFACES AND INTERFACES 175
7.5 DBAS IN OPTOELECTRONIC APPLICATIONS 180
7.6 DBAS AS SYNTHETIC PRECURSORS 181
7.6.1 TRANSANNULAR BOND FORMATION LEADING TO UNCONVENTIONAL AROMATIC
MOLECULES 181
7.6.2 STRAIN-ASSISTED CYCLOADDITION AND BIOLOGICAL APPLICATIONS 185
7.7 SUMMARY AND CONCLUSIONS 187
REFERENCES 187
8 TETRAARYLETHENES AND AGGREGATION-INDUCED EMISSION 193
ZUJIN ZHAO
AND BEN
ZHONG TANG
8.1 INTRODUCTION 193
8.2 FUNDAMENTALS 194
8.2.1 PRISTINE TETRAPHENYLETHENE (TPE) 194
8.2.2 RIGIDIFIED TPE DERIVATIVES 195
8.2.3 ADDUCTS OF TPE AND PLANAR CHROMOPHORES 200
8.2.4 EMISSION COLOR TUNING OF TPE DERIVATIVES 202
8.2.5 COMPLEX TETRAARYLETHENES 204
8.3 APPLICATIONS 210
8.3.1 CHEMOSENSORS 210
8.3.2 MECHANOCHROMIC LUMINESCENT MATERIALS 211
8.3.3 LIGHT-EMITTING MATERIALS 213
VIIII
CONTENTS
8.4 OUTLOOK 218
REFERENCES 219
PART II POLYCYDIC HETEROARENES 223
9 A/-CONTAINING POLYCYDIC HETEROARENES 225
ARUN NAIBI LAKSHMINARAYANA
AND CHUNYAN
CHI
9.1 INTRODUCTION 225
9.2 LINEAR AND EXTENDED N-HETEROARENES 226
9.2.1 AF-HETEROACENES 226
9.2.1.1 HISTORY AND SYNTHESIS 226
9.2.1.2 PROPERTIES AND APPLICATIONS 228
9.2.2 EXTENDED IV-HETEROARENES 232
9.2.2.1 UNCONVENTIONAL AF-HETEROACENES 232
9.2.2.2 A/-ANNULATED PERYLENES 235
9.3 NITROGEN-RICH MACROCYCLIC ARENES 236
9.3.1 PORPHYRIN AND PORPHYRINOIDS 236
9.3.1.1 SYNTHESIS 237
9.3.1.2 GENERAL PROPERTIES 237
9.3.1.3 DIVERSITY OF PORPHYRINOIDS 239
9.3.1.4 APPLICATIONS 241
9.3.2 PHTHALOCYANINES 242
9.3.2.1 HISTORY AND SYNTHESIS 242
9.3.2.2 GENERAL PROPERTIES AND APPLICATIONS 243
9.4 MISCELLANEOUS 244
9.5 SUMMARY AND CONCLUSION 246
REFERENCES 247
10 BORON-CONTAINING POLYCYDIC AROMATICS 251
DAVID R. LEVINE AND
JOHN D. TOVAR
10.1 INTRODUCTION 251
10.2 HISTORICAL PERSPECTIVE AND REPRESENTATIVE STRUCTURES 251
10.3 GENERAL SYNTHETIC STRATEGIES 253
10.3.1 METALATION/RING CLOSURE 253
10.3.2 ELEMENT-BORON EXCHANGE (METATHESIS) 254
10.3.3 INTRAMOLECULAR CASCADE CYCLIZATIONS 255
10.3.4 PHOTOISOMERIZATION/THERMAL ISOMERIZATION 256
10.3.5 OXIDATIVE AND RADICAL CYCLIZATIONS - TOWARD TWO-DIMENSIONAL
JR-SYSTEMS 257
10.3.6 FUNCTIONALIZATION AT BORON: HYDROBORATION CHEMISTRY 258
10.4 RECENT DEVELOPMENTS IN B-PAH STRUCTURES AND PROPERTIES 259
10.4.1 LINEAR LADDER-TYPE JT-SYSTEMS 259
10.4.1.1 BOROLE-BASED PAHS 259
10.4.1.2 BOREPIN-BASED PAHS 261
10.4.1.3 BORAACENES AND THEIR CONGENERS 262
CONTENTS | IX
10.4.1.4 TETRAVALENT BORON: B-N COORDINATED AND OTHER ZWITTERIONIC
SYSTEMS 265
10.4.2 TWO-DIMENSIONALLY FUSED JT-SYSTEMS 267
10.4.2.1 FUNDAMENTAL IMPACTS OF ENFORCED PLANARITY IN TRIARYLBORANES 267
10.4.2.2 FULLY CONJUGATED TWO-DIMENSIONAL MATERIALS 270
10.5 CONCLUSIONS/OUTLOOK 272
REFERENCES 273
11 S-CONTAINING POLYCYCLIC HETEROARENES: THIOPHENE-FUSED AND
THIADIAZOLE-FUSED ARENES AS ORGANIC SEMICONDUCTORS 277
MASASHI MAMADA
AND YOSHIRO
YAMASHITA
11.1 INTRODUCTION 277
11.2 ELECTRONIC STRUCTURES OF FUSED THIOPHENES AND THIADIAZOLES 278
11.3 P-TYPE SEMICONDUCTORS WITH FUSED THIOPHENES 282
11.3.1 ACENOTHIOPHENES (ACTS) AND ACENODITHIOPHENES (ACDTS) 282
11.3.1.1 OVERVIEW 282
11.3.1.2 ACT AND ACDT DERIVATIVES 284
11.3.1.3 ACT AND ACDT DERIVATIVES WITH TRIALKYLSILYLETHYNYL GROUPS 284
11.3.2 [W]THIENOACENES ([]TACS) AND RELATED COMPOUNDS 286
11.3.2.1 OVERVIEW 286
11.3.2.2
[M]
TA
C
DERIVATIVES 286
11.3.3 ALTERNATING RINGS OF FUSED BENZENE AND THIOPHENE MOLECULES
(ABTS) 288
11.3.3.1 OVERVIEW 288
11.3.3.2 ISOELECTRONIC ANALOGS OF DIBENZO[A,//]ANTHRACENE 290
11.3.3.3 ISOELECTRONIC ANALOGS OF PENTAPHENE 290
11.3.3.4 ISOELECTRONIC ANALOGS OF BENZO [A]
TETRACENE 290
11.3.4 DIACENE-FUSED THIENOTHIOPHENES (DACTTS) 290
11.3.4.1 OVERVIEW 290
11.3.4.2 SYMMETRIC DACTTS 291
11.3.4.3 ASYMMETRIC DACTTS 291
11.3.5 OTHERS (2-D IT-EXTENDED FUSED THIOPHENES) 293
11.3.5.1 OVERVIEW 293
11.3.5.2 2-D JC-EXTENDED FUSED THIOPHENES 293
11.4 N-TYPE SEMICONDUCTORS WITH FUSED THIOPHENES 293
11.4.1 OVERVIEW 293
11.4.2 N-TYPE SEMICONDUCTORS WITH FUSED THIOPHENES 295
11.5 THIADIAZOLE DERIVATIVES 297
11.5.1 OVERVIEW 297
11.5.2 THIADIAZOLE DERIVATIVES FOR P-TYPE SEMICONDUCTORS 298
11.5.3 THIADIAZOLE DERIVATIVES FOR AMBIPOLAR SEMICONDUCTORS 298
11.5.4 THIADIAZOLE DERIVATIVES FOR N-TYPE SEMICONDUCTORS 300
11.6 SUMMARY AND CONCLUSIONS 300
REFERENCES 303
X | CONTENTS
12 P-CONTAINING HETEROARENES: SYNTHESIS, PROPERTIES, APPLICATIONS 309
MONIKA STOLAR
AND THOMAS BAUMGARTNER
12.1 INTRODUCTION 309
12.2 FIVE-MEMBERED RING SYSTEMS 309
12.3 SIX-MEMBERED RING SYSTEMS 321
12.4 SEVEN-MEMBERED RING SYSTEMS 323
12.5 OTHER PHOSPHORUS-CONTAINING DIKETO-RING SYSTEMS 325
12.6 SUMMARY AND CONCLUSIONS 326
ACKNOWLEDGMENTS 327
REFERENCES 327
INDEX
331 |
| any_adam_object | 1 |
| author2 | Miao, Qian |
| author2_role | edt |
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| dewey-ones | 540 - Chemistry and allied sciences |
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| discipline | Chemie / Pharmazie |
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| id | DE-604.BV043173952 |
| illustrated | Illustrated |
| indexdate | 2024-09-10T01:57:19Z |
| institution | BVB |
| isbn | 3527338470 9783527338474 9783527689545 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-028598076 |
| oclc_num | 909797016 |
| open_access_boolean | |
| owner | DE-11 DE-29 DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-29 DE-19 DE-BY-UBM |
| physical | XVI, 337 Seiten Illustrationen, Diagramme |
| publishDate | 2016 |
| publishDateSearch | 2016 |
| publishDateSort | 2016 |
| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Polycyclic arenes and heteroarenes synthesis, properties, and applications edited by Qian Miao Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2016] © 2016 XVI, 337 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Heteroaromaten (DE-588)4159717-5 gnd rswk-swf Polycyclische Aromaten (DE-588)4175141-3 gnd rswk-swf Chemie Chemistry Electrical & Electronics Engineering Elektrotechnik u. Elektronik Halbleiter Nanomaterialien Nanomaterials Nanotechnologie Nanotechnology Semiconductors Supramolecular Chemistry Supramolekulare Chemie Polycyclische Aromaten (DE-588)4175141-3 s Heteroaromaten (DE-588)4159717-5 s DE-604 Miao, Qian (DE-588)1079393692 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-68957-6 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-68956-9 Erscheint auch als Online-Ausgabe, PDF 978-3-527-68955-2 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=5249469&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028598076&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Polycyclic arenes and heteroarenes synthesis, properties, and applications Heteroaromaten (DE-588)4159717-5 gnd Polycyclische Aromaten (DE-588)4175141-3 gnd |
| subject_GND | (DE-588)4159717-5 (DE-588)4175141-3 |
| title | Polycyclic arenes and heteroarenes synthesis, properties, and applications |
| title_auth | Polycyclic arenes and heteroarenes synthesis, properties, and applications |
| title_exact_search | Polycyclic arenes and heteroarenes synthesis, properties, and applications |
| title_full | Polycyclic arenes and heteroarenes synthesis, properties, and applications edited by Qian Miao |
| title_fullStr | Polycyclic arenes and heteroarenes synthesis, properties, and applications edited by Qian Miao |
| title_full_unstemmed | Polycyclic arenes and heteroarenes synthesis, properties, and applications edited by Qian Miao |
| title_short | Polycyclic arenes and heteroarenes |
| title_sort | polycyclic arenes and heteroarenes synthesis properties and applications |
| title_sub | synthesis, properties, and applications |
| topic | Heteroaromaten (DE-588)4159717-5 gnd Polycyclische Aromaten (DE-588)4175141-3 gnd |
| topic_facet | Heteroaromaten Polycyclische Aromaten |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=5249469&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028598076&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT miaoqian polycyclicarenesandheteroarenessynthesispropertiesandapplications |