Functional organic materials: syntheses, strategies and applications
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| 245 | 1 | 0 | |a Functional organic materials |b syntheses, strategies and applications |c ed. by Thomas J. J. Müller ... |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2007 | |
| 300 | |a XX, 591 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Compuestos orgánicos | |
| 650 | 0 | 7 | |a Makromolekulare Chemie |0 (DE-588)4168684-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organischer Stoff |0 (DE-588)4203832-7 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Makromolekulare Chemie |0 (DE-588)4168684-6 |D s |
| 689 | 0 | 1 | |a Organischer Stoff |0 (DE-588)4203832-7 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Müller, Thomas J. J. |e Sonstige |0 (DE-588)11370979X |4 oth | |
| 856 | 4 | 2 | |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=2831372&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
| 856 | 4 | 2 | |m Digitalisierung UB Augsburg |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015050583&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-015050583 | |
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| _version_ | 1805088543953911808 |
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| adam_text |
Contents
Preface
Xi
11
List of Contributors
XVIII
Part I
3-D
Carbon-rich
π
-Systems
- Nanotubes and Segments
1
Fu
nationalization of Carbon Nanotubes
3
Andreas
Hirsch
and Otto Vostrowsky
1.1
introduction to Carbon Nanotubes
-
A New Carbon
Allotropé
3
1.2
Funcţionalization
of Carbon Nanotubes
4
1.3
Covalent
Funcţionalization
5
1.3.1
Halogenation of Carbon Nanotubes
5
1.3.1.1
Fluorination of Carbon Nanotubes
5
1.3.1.2
Chlorination of Carbon Nanotubes
7
1.3.1.3
В
rom i
nation of
M
WC NTs
7
1.3.1.4
Chemical Derivatization of "Fluoronanotubes"
7
1.3.2
Oxidation of CNTs
-
Oxidative Purification
8
1.3.2.1
Carbóxylation
of CNTs
8
1.3.2.2
Defect
Funcţionalization
-Transformation of Carboxylic Functions
10
1.3.3
Hydrogénation
of Carbon Nanotubes
Ï9
1.3.4
Addition of Radicals
19
1.3.5
Addition of Nucleophilic Carbenes
20
1.3.6
Sidewall
Funcţionalization
Through Electrophilic Addition
2Ί
1.3.7
Funcţionalization
Through
Cycloadditions
21
1.3.7.1
Addition of Carbenes
21
1.3.7.2
Addition of Nitrenes
22
1.3.7.3
Nucleophilic Cyclopropanation
-
Binge) Reaction
24
1.3.7.4
Azomethine Ylides
24
1.3.7.5
[4+21-Cycloaddition
-
Diels-Alder Reaction
26
1.3.7.6
Sidewall Osmylation of Individual SWCNTs
27
1.3.8
Aryl Diazonium Chemistry
-
Electrochemical Modification
of Nanotubes
27
VI
Contents
1.3.9
Reductive Alkylation and Arylation of Carbon Nanotubes
29
1.3.10
Addition of Carbani
ons
-
Reactions with Alkyllithiura
30
1.3.11
Covalent Functionalization by Polymerization
-
"Grafting To" and "Grafting From"
31
1.4 .
Noncovaient Exohedral Functionalization
-
Functionalization with Biomolecules
32
1.5
Endohedral Functionalization
42
1.6
Conclusions
44
1.7
Experimental
44
-
References
49
2
Cyclophenacene Cut Out of
Fullerene
59
Yutaka Matsuo and Eiichi Nakamura
2.1
Introduction
59
2.2
Synthesis of [lOjCyclophenacene
π
-Conjugated
Systems
from [60]Fullerene
63
2.2.1
Synthetic Strategy
63
2.2.2
Synthesis and Characterization of [lOJCyclophenacenes
64
2.2.3
Structural Studies and Aromaticity of [lOjCyclophenacene
67
2.2.4
Synthesis of Dibenzo-fused Corannulenes
69
2.2.5
Absorption and Emission of [lOjCyclophenacenes
and Dibenzo Fused Corannulenes
70
2.3
Conclusion
72
2.4
Experimental
72
'
References
78
Part II Strategic Advances in Chromophore and Materials Synthesis
3
Cruciform it-Conjugated
Oligomers
83
Frank
Galbrecht, Torsten
W.
Bünnagel,
. Askin Bilge, Ullrich
Scherf and
Tony Farrell
3.1
Introduction
83
3.2
Oligomers
with a Tetrahedral Core Unit
85
3.3
Oligomers
with a Tetrasubstituted Benzene Core
91
3.4
Oligomers
with a Tetrasubstituted Biaryl Core
95
3.5
Conclusion
113
3.6
Experimental
113
Acknowledgments
115
References
116
Co
4
Design of re-Conjugated Systems Using Organophosphorus
Building Blocks
119
Philip W. Dyer and
Régis Réau
4.1
Introduction
119
4.2
Phosphole-containing it-Conjugated Systems
121
4.2.1
a,u'-Oligo{phosphole)s
123
4.2.2
Derivatives Based on
ІД'
-Biphosphole
Units
126
4.2.3
Mixed
Oligomers
Based on Phospholes
with Other
(Hetero)aromatics
129
4.2.4
Mixed
Oligomers
Based on Biphospholes
with other
(Hetero)aromatics
137
4.2.5
Mixed
Oligomers
Based on Phospholes
with Ethenyl or Ethynyl Units
138
4.2.6
Polymers Incorporating Phospholes
140
4.2.7
Mixed
Oligomers
and Polymers Based
on Dibenzophosphole or Dithienophosphole
143
4.3
Phosphine-containing
π
-Conjugated
Systems
147
4.3.1
Polymers Based on p-Phenylenephosphine Units
147
4.3.2
Oligomers
Based on Phosphine-Ethynyl Units
151
4.3.3
Mixed Derivatives Based on Arylphosphino Units
155
4.4
Phosphaalkene- and Diphosphene-containing
π
-Conjugated
Systems
161
4.5
Conclusion
268
4.6
Selected Experimental Procedures
169
References
172
5
Diversity-oriented Synthesis of Chromophores
by Combinatorial Strategies and Multi-component Reactions
179
Thomas J. J.
Müller
5.1
Introduction
179
5.2
Combinatorial Syntheses of Chromophores
180
5.2.1
Combinatorial
Azo
Coupling
181
5.2.2
Combinatorial Condensation Reactions
182
5.2.3
Combinatorial Cross-coupling Reactions
187
5.2.4
Combinatorial Coordination Chemistry
197
5.3
Novel Multi-component Syntheses of Chromophores
199
5.3.1
Multi-component Condensation Reactions
199
5.3.2
Multi-component Cross-coupling Reactions
204
5.4
Conclusion and Outlook
215
5.5
Experimental Procedures
215
References
218
VIII Contents
6
High-yield Synthesis of Shape-persistent
Phenylene-Ethynylene
Macrocycles
225
Sigurd
Höger
6.1
introduction
225
6.2
Synthesis
227
6.2.1
General
227
6.2.2
The Kinetic Approach
227
6.2.2.1
Statistical Reactions
227
6.2.2.2
Template-controlled Cyclizations
238
6.2.3
The Thermodynamic Approach
251
6.3
Conclusion
254
6.4
Experimental Procedures
255
References
258
7
Functional Materials via Multiple Noncovalent Interactions
261
Joseph R. Carlisle and Marcus Week
7.1
Introduction
261
7.2
Biologically Inspired Materials via Multi-step Self-assembly
262
7.3
Small Molecule-based Multi-step Self-assembly
265
7.4
Polymer-based Self-assembly
275
7.4.1
Main-chain Self-assembly
276
7.4.2
Side-chain Self-assembly
279
Ί
'.4.3
Macroscopic Self-assembly
287
7.5
Conclusion and Outlook
288
References
289
Part
IM
Molecular Muscles, Switches and Electronics
8
Molecular Motors and Muscles
295
Sourav Saha and J.
Fraser Stoddart
8.1
Introduction
295
8.2
Mechanically Interlocked Molecules as Artificial
Molecular Machines
297
8.3
Chemically Induced Switching of the Bistable Rotaxanes
299
8.3.1
A Bistable [2]Rotaxane Driven by Acid-Base Chemistry
300
8.3.2
A pH-driven Molecular Elevator
301
8.3.3
A Molecular Muscle Powered by Metal Ion Exchange
303
8.3.4
Redox
and Chemically Controlled Molecular Switches and Muscles
304
8.3.4.1
Solution-phase Switching
305
8.3.4.2
Condensed-phase Switching
306
8.3.4.3
A Solid-state Nanomechanical Device
308
8.4
Electrochemically Controllable Bistable Rotaxanes
309
8.4.1
A Benzidine/Biphenol-based Molecular Switch
310
Contents
IX
8.4.2 Electrochemically
Controlled Switching of
TTF/DNP-based [2]Rotaxanes
311
8.4.2.1
Solution-phase Switching
311
8.4.2.2
Metastability of a Redox-driven [2]Rotaxane SAM on Gold Surfaces
311
8.4.2.3
A TTF/DNP
ßjRotaxane-based Electrochromic
Device
313
8.4.2.4
A Redox-driven pjRotaxane-based Molecular
Switch Tunnel Junctions (MSTJs) Device
314
8.4.3
A Redox
and Chemically Controllable Bistable Neutral [2]Rotaxane
315
S
A3
Λ
Electrochemical Switching
315
8.4.3.2
Chemical Switching Induced by Lithium Ion (Li+)
316
8.5
Photochemically Powered Molecular Switches
316
8.5.1
Molecular Switching Caused by Photoisomerization
317
8.5.2
PET-induced Switching of an
Н
-bonded Molecular Motor
318
8.5.3
MLCT-induced Switching of a Metal Ion-based Molecular Motor
319
8.5.4
A Photo-driven Molecular Abacus
320
8.6
Conclusions
322
Acknowledgments
322
References
323
9
Diarylethene as a Photoswitching Unit of Intramolecular
Magnetic Interaction
329
Kenji Matsuda and Masahiro Irie
9.1
Introduction
329
9.2
Photochromic Spin Coupler
331
9.3
Synthesis of Diarylethene Biradicals
333
9.4
Photoswitching Using Bis(3-thienyl)ethene
335
9.5
Reversed Photoswitching Using Bis(2-thienyl)ethene
340
9.6
Photoswitching Using an Array of Photochromic Molecules
341
9.7
Development of a New Switching Unit
344
9.8
Conclusions
348
9.9
Experimental Procedures
348
Acknowledgments
349
References
350
10
Thiol End-capped Molecules for Molecular Electronics: Synthetic Methods,
Molecular junctions and Structure-Property Relationships
353
Kasper
Nergaard,
Mogens
Br0ndsted Nielsen and Thomas Bjemholm
10.1
Introduction
353
10.2
Synthetic Procedures
354
10.2.1
Protecting Groups for Arylthiols
354
10.2.1.1
Synthesis of Arylthiol "Alligator Clips"
354
10.2.2
One-terminal Wires
358
10.2.3
Two-terminal Wires
359
10.2.4
Three-terminal Wires
364
Contents
10.2.5
Four-terminal Wires
365
10.2.6
Caltrops
367
10.3
Electron Transport in Two- and Three-terminal Molecular Devices
368
10.3.1
Molecular Junctions
375
10.3.1.1
Scanning Tunneling-based Molecular Junctions
375
10.3.1.2
Conducting-probe Atomic Force Microscopy
379
10.3.1.3
Solution-phase Molecular STM Junctions
380
10.3.1.4
Break Junctions
381
10.3.1.5
Crossed Wires
382
10.3.1.6
Nanopore Junctions
382
10.3.1.7
Square-tip Junctions
383
10.3.1.8
Mercury Drop Junctions
384
10.3.1.9
Particle Junctions
384
10.3.1.10
Nanowire Junctions
385
10.3.1.11
Three-terminal Single-molecule Transistors
386
10.4
Summary and Outlook
387
10.5
Experimental
388
References
389
11
Nonlinear Optical Properties of Organic Materials
393
Stephen Barlow and Seth R.
Marder
11.1
Introduction to Nonlinear Optics
393
11.1.1
Introduction
393
11.1.2
Linear and Nonlinear Polarization
394
11.1.3
Second-order Nonlinear Optical Effects
396
11.1.4
.Measurement Techniques for Second-order Properties,
β
and
χ{2)
397
11.1.5
Third-order Nonlinear Optical Effects
399
11.1.6
Measurement Techniques for 2PA Cross-section,
ò
401
11.2
Second-order Chromophores for Electrooptic Applications
404
11.2.1
Design of Second-order Chromophores: the Two-level Model
404
11.2.2
Other Chromophore Designs
409
11.2.3
Other Considerations
411
11.2.4
High-performance Electooptic Poled-polymer Systems 4J3
11.3
Design and Application of Two-photon Absorbing Chromophores
418
11.3.1
Essential-state Models for Two-photon Cross-section
418
11.3.2
Chromophore Designs
420
11.3.3
Applications of Two-photon Absorption
427
11.4
Appendix: Units in
NLO
430
Acknowledgments
431
References
431
Contents )
Part IV
Electronic
Interaction and Structure
12
Photoinduced Electron Transfer Processes
in Synthetically Modified
DNA 441
Hans-Achim Wagenknecht
12.1 DNA
as a Bioorgamc Material for Electron Transport
441
12.2
Mechanism of Hole Transfer and Hole Hopping in
DNA 444
12.3
Reductive Electron Transfer and Excess Electron Transport
in
DNA 446
12.3.1
Strategies for the Synthesis of
DNA
Donor-Acceptor Systems
446
12.3.2
Chromophore Functionalization of
DNA
Bases via Synthesis
of
DNA
Building Blocks
448
12.3.3 DNA
Base Modifications via a Solid-phase Synthetic Strategy
452
12.3.4
Chromophores as Artificial
DNA
Base Substitutes
454
12.4
Results from the Electron Transfer Studies
456
12.5
Outlook: Towards Synthetic Nanostructures Based
on DNA-like Architecture
460
References
463
13
Electron Transfer of ^-Functional Systems and Applications
465
Shunichi Fukuzumi
13.1
Introduction
465
13.2
Efficient Electron-transfer Properties of Zinc Porphyrins
467
13.3
Efficient Electron-transfer Properties of Fullerenes
474
13.4
Photoinduced Electron Transfer in Electron Donor-Acceptor
Linked Molecules Mimicking the Photosynthetic Reaction Center
477
13.5
An Orthogonal
π
-Donor-
Acceptor Dyad Affording
an Infinite CS Lifetime
485
13.6
A Long-lived
ET
State Acting as an Efficient
ET Photocatalyst 490
13.7
Organic Solar Cells Using Simple Donor-Acceptor Dyads
494
13.8
Organic Solar Cells Composed of Multi-porphyrin/Qo
Supramolecular Assemblies
499
13.9
Conclusion
506
Acknowledgments
506
References
507
14
Induced Jt-Stacking in
Acenes
511
John E. Anthony
14.1
Introduction
52 2
14.2
Anthracene
522
14.2.1
Monosubstituted Anthracene
514
14.2.2
Disubstituted Anthracene
517
14.2.3
Edge-substituted Anthracenes
(Anthracene Functionalized at the
1,8-
or 1,8,9-Positions)
522
XII Contents
14.2.4 Liquid
Crystalline Anthracenes
525
14.2.5
Anthracene Self-assembly: Hydrogen Bonding
526
14.3
Tetracene (Naphthacene)
528
14.3.1
Ethynyltetracenes
530
14.3.2
Tetrasubstituted Tetracenes
532
14.4
Pentacene
534
14.5
Higher
Acenes
540
14.6
Conclusion
541
Acknowledgments
542
References
542
15
Synthesis and Characterization of Novel Chiral Conjugated Materials
547
Andrzej Rajca
and Makoto Miyasaka
15.1
Introduction
547
15.2
Synthetic Approaches to Highly Annelated Chiral
π
-Conjugated
Systems
548
15.2.1
Helicenes
548
15.2.1.1
Photochemical Syntheses
549
15.2.1.2
Non-photochemical Syntheses
551
15.2.2
Double Helicenes and Chiral Polycyclic Aromatic Hydrocarbons
560
15.2.3
Tetraphenylenes and
π
-Conjugated
Double Helices
563
15.3
Barriers for Racemization of Chiral
π
-Conjugated
Systems
567
15.4
Strong Chiroptical Properties in Absorption,
Emission and Refraction
570
15.4.1
Absorption and Emission
570
15.4.2
Refraction
572
15.5
Conclusion
574
Acknowledgments
574
References
574
Index
583 |
| adam_txt |
Contents
Preface
Xi
11
List of Contributors
XVIII
Part I
3-D
Carbon-rich
π
-Systems
- Nanotubes and Segments
1
Fu
nationalization of Carbon Nanotubes
3
Andreas
Hirsch
and Otto Vostrowsky
1.1
introduction to Carbon Nanotubes
-
A New Carbon
Allotropé
3
1.2
Funcţionalization
of Carbon Nanotubes
4
1.3
Covalent
Funcţionalization
5
1.3.1
Halogenation of Carbon Nanotubes
5
1.3.1.1
Fluorination of Carbon Nanotubes
5
1.3.1.2
Chlorination of Carbon Nanotubes
7
1.3.1.3
В
rom i
nation of
M
WC NTs
7
1.3.1.4
Chemical Derivatization of "Fluoronanotubes"
7
1.3.2
Oxidation of CNTs
-
Oxidative Purification
8
1.3.2.1
Carbóxylation
of CNTs
8
1.3.2.2
Defect
Funcţionalization
-Transformation of Carboxylic Functions
10
1.3.3
Hydrogénation
of Carbon Nanotubes
Ï9
1.3.4
Addition of Radicals
19
1.3.5
Addition of Nucleophilic Carbenes
20
1.3.6
Sidewall
Funcţionalization
Through Electrophilic Addition
2Ί
1.3.7
Funcţionalization
Through
Cycloadditions
21
1.3.7.1
Addition of Carbenes
21
1.3.7.2
Addition of Nitrenes
22
1.3.7.3
Nucleophilic Cyclopropanation
-
Binge) Reaction
24
1.3.7.4
Azomethine Ylides
24
1.3.7.5
[4+21-Cycloaddition
-
Diels-Alder Reaction
26
1.3.7.6
Sidewall Osmylation of Individual SWCNTs
27
1.3.8
Aryl Diazonium Chemistry
-
Electrochemical Modification
of Nanotubes
27
VI
Contents
1.3.9
Reductive Alkylation and Arylation of Carbon Nanotubes
29
1.3.10
Addition of Carbani
ons
-
Reactions with Alkyllithiura
30
1.3.11
Covalent Functionalization by Polymerization
-
"Grafting To" and "Grafting From"
31
1.4 .
Noncovaient Exohedral Functionalization
-
Functionalization with Biomolecules
32
1.5
Endohedral Functionalization
42
1.6
Conclusions
44
1.7
Experimental
44
-
References
49
2
Cyclophenacene Cut Out of
Fullerene
59
Yutaka Matsuo and Eiichi Nakamura
2.1
Introduction
59
2.2
Synthesis of [lOjCyclophenacene
π
-Conjugated
Systems
from [60]Fullerene
63
2.2.1
Synthetic Strategy
63
2.2.2
Synthesis and Characterization of [lOJCyclophenacenes
64
2.2.3
Structural Studies and Aromaticity of [lOjCyclophenacene
67
2.2.4
Synthesis of Dibenzo-fused Corannulenes
69
2.2.5
Absorption and Emission of [lOjCyclophenacenes
and Dibenzo Fused Corannulenes
70
2.3
Conclusion
72
2.4
Experimental
72
'
References
78
Part II Strategic Advances in Chromophore and Materials Synthesis
3
Cruciform it-Conjugated
Oligomers
83
Frank
Galbrecht, Torsten
W.
Bünnagel,
. Askin Bilge, Ullrich
Scherf and
Tony Farrell
3.1
Introduction
83
3.2
Oligomers
with a Tetrahedral Core Unit
85
3.3
Oligomers
with a Tetrasubstituted Benzene Core
91
3.4
Oligomers
with a Tetrasubstituted Biaryl Core
95
3.5
Conclusion
113
3.6
Experimental
113
Acknowledgments
115
References
116
Co
4
Design of re-Conjugated Systems Using Organophosphorus
Building Blocks
119
Philip W. Dyer and
Régis Réau
4.1
Introduction
119
4.2
Phosphole-containing it-Conjugated Systems
121
4.2.1
a,u'-Oligo{phosphole)s
123
4.2.2
Derivatives Based on
ІД'
-Biphosphole
Units
126
4.2.3
Mixed
Oligomers
Based on Phospholes
with Other
(Hetero)aromatics
129
4.2.4
Mixed
Oligomers
Based on Biphospholes
with other
(Hetero)aromatics
137
4.2.5
Mixed
Oligomers
Based on Phospholes
with Ethenyl or Ethynyl Units
138
4.2.6
Polymers Incorporating Phospholes
140
4.2.7
Mixed
Oligomers
and Polymers Based
on Dibenzophosphole or Dithienophosphole
143
4.3
Phosphine-containing
π
-Conjugated
Systems
147
4.3.1
Polymers Based on p-Phenylenephosphine Units
147
4.3.2
Oligomers
Based on Phosphine-Ethynyl Units
151
4.3.3
Mixed Derivatives Based on Arylphosphino Units
155
4.4
Phosphaalkene- and Diphosphene-containing
π
-Conjugated
Systems
161
4.5
Conclusion
268
4.6
Selected Experimental Procedures
169
References
172
5
Diversity-oriented Synthesis of Chromophores
by Combinatorial Strategies and Multi-component Reactions
179
Thomas J. J.
Müller
5.1
Introduction
179
5.2
Combinatorial Syntheses of Chromophores
180
5.2.1
Combinatorial
Azo
Coupling
181
5.2.2
Combinatorial Condensation Reactions
182
5.2.3
Combinatorial Cross-coupling Reactions
187
5.2.4
Combinatorial Coordination Chemistry
197
5.3
Novel Multi-component Syntheses of Chromophores
199
5.3.1
Multi-component Condensation Reactions
199
5.3.2
Multi-component Cross-coupling Reactions
204
5.4
Conclusion and Outlook
215
5.5
Experimental Procedures
215
References
218
VIII Contents
6
High-yield Synthesis of Shape-persistent
Phenylene-Ethynylene
Macrocycles
225
Sigurd
Höger
6.1
introduction
225
6.2
Synthesis
227
6.2.1
General
227
6.2.2
The Kinetic Approach
227
6.2.2.1
Statistical Reactions
227
6.2.2.2
Template-controlled Cyclizations
238
6.2.3
The Thermodynamic Approach
251
6.3
Conclusion
254
6.4
Experimental Procedures
255
References
258
7
Functional Materials via Multiple Noncovalent Interactions
261
Joseph R. Carlisle and Marcus Week
7.1
Introduction
261
7.2
Biologically Inspired Materials via Multi-step Self-assembly
262
7.3
Small Molecule-based Multi-step Self-assembly
265
7.4
Polymer-based Self-assembly
275
7.4.1
Main-chain Self-assembly
276
7.4.2
Side-chain Self-assembly
279
Ί
'.4.3
Macroscopic Self-assembly
287
7.5
Conclusion and Outlook
288
References
289
Part
IM
Molecular Muscles, Switches and Electronics
8
Molecular Motors and Muscles
295
Sourav Saha and J.
Fraser Stoddart
8.1
Introduction
295
8.2
Mechanically Interlocked Molecules as Artificial
Molecular Machines
297
8.3
Chemically Induced Switching of the Bistable Rotaxanes
299
8.3.1
A Bistable [2]Rotaxane Driven by Acid-Base Chemistry
300
8.3.2
A pH-driven Molecular Elevator
301
8.3.3
A Molecular Muscle Powered by Metal Ion Exchange
303
8.3.4
Redox
and Chemically Controlled Molecular Switches and Muscles
304
8.3.4.1
Solution-phase Switching
305
8.3.4.2
Condensed-phase Switching
306
8.3.4.3
A Solid-state Nanomechanical Device
308
8.4
Electrochemically Controllable Bistable Rotaxanes
309
8.4.1
A Benzidine/Biphenol-based Molecular Switch
310
Contents
IX
8.4.2 Electrochemically
Controlled Switching of
TTF/DNP-based [2]Rotaxanes
311
8.4.2.1
Solution-phase Switching
311
8.4.2.2
Metastability of a Redox-driven [2]Rotaxane SAM on Gold Surfaces
311
8.4.2.3
A TTF/DNP
ßjRotaxane-based Electrochromic
Device
313
8.4.2.4
A Redox-driven pjRotaxane-based Molecular
Switch Tunnel Junctions (MSTJs) Device
314
8.4.3
A Redox
and Chemically Controllable Bistable Neutral [2]Rotaxane
315
S
A3
Λ
Electrochemical Switching
315
8.4.3.2
Chemical Switching Induced by Lithium Ion (Li+)
316
8.5
Photochemically Powered Molecular Switches
316
8.5.1
Molecular Switching Caused by Photoisomerization
317
8.5.2
PET-induced Switching of an
Н
-bonded Molecular Motor
318
8.5.3
MLCT-induced Switching of a Metal Ion-based Molecular Motor
319
8.5.4
A Photo-driven Molecular Abacus
320
8.6
Conclusions
322
Acknowledgments
322
References
323
9
Diarylethene as a Photoswitching Unit of Intramolecular
Magnetic Interaction
329
Kenji Matsuda and Masahiro Irie
9.1
Introduction
329
9.2
Photochromic Spin Coupler
331
9.3
Synthesis of Diarylethene Biradicals
333
9.4
Photoswitching Using Bis(3-thienyl)ethene
335
9.5
Reversed Photoswitching Using Bis(2-thienyl)ethene
340
9.6
Photoswitching Using an Array of Photochromic Molecules
341
9.7
Development of a New Switching Unit
344
9.8
Conclusions
348
9.9
Experimental Procedures
348
Acknowledgments
349
References
350
10
Thiol End-capped Molecules for Molecular Electronics: Synthetic Methods,
Molecular junctions and Structure-Property Relationships
353
Kasper
Nergaard,
Mogens
Br0ndsted Nielsen and Thomas Bjemholm
10.1
Introduction
353
10.2
Synthetic Procedures
354
10.2.1
Protecting Groups for Arylthiols
354
10.2.1.1
Synthesis of Arylthiol "Alligator Clips"
354
10.2.2
One-terminal Wires
358
10.2.3
Two-terminal Wires
359
10.2.4
Three-terminal Wires
364
Contents
10.2.5
Four-terminal Wires
365
10.2.6
Caltrops
367
10.3
Electron Transport in Two- and Three-terminal Molecular Devices
368
10.3.1
Molecular Junctions
375
10.3.1.1
Scanning Tunneling-based Molecular Junctions
375
10.3.1.2
Conducting-probe Atomic Force Microscopy
379
10.3.1.3
Solution-phase Molecular STM Junctions
380
10.3.1.4
Break Junctions
381
10.3.1.5
Crossed Wires
382
10.3.1.6
Nanopore Junctions
382
10.3.1.7
Square-tip Junctions
383
10.3.1.8
Mercury Drop Junctions
384
10.3.1.9
Particle Junctions
384
10.3.1.10
Nanowire Junctions
385
10.3.1.11
Three-terminal Single-molecule Transistors
386
10.4
Summary and Outlook
387
10.5
Experimental
388
References
389
11
Nonlinear Optical Properties of Organic Materials
393
Stephen Barlow and Seth R.
Marder
11.1
Introduction to Nonlinear Optics
393
11.1.1
Introduction
393
11.1.2
Linear and Nonlinear Polarization
394
11.1.3
Second-order Nonlinear Optical Effects
396
11.1.4
.Measurement Techniques for Second-order Properties,
β
and
χ{2)
397
11.1.5
Third-order Nonlinear Optical Effects
399
11.1.6
Measurement Techniques for 2PA Cross-section,
ò
401
11.2
Second-order Chromophores for Electrooptic Applications
404
11.2.1
Design of Second-order Chromophores: the Two-level Model
404
11.2.2
Other Chromophore Designs
409
11.2.3
Other Considerations
411
11.2.4
High-performance Electooptic Poled-polymer Systems 4J3
11.3
Design and Application of Two-photon Absorbing Chromophores
418
11.3.1
Essential-state Models for Two-photon Cross-section
418
11.3.2
Chromophore Designs
420
11.3.3
Applications of Two-photon Absorption
427
11.4
Appendix: Units in
NLO
430
Acknowledgments
431
References
431
Contents )
Part IV
Electronic
Interaction and Structure
12
Photoinduced Electron Transfer Processes
in Synthetically Modified
DNA 441
Hans-Achim Wagenknecht
12.1 DNA
as a Bioorgamc Material for Electron Transport
441
12.2
Mechanism of Hole Transfer and Hole Hopping in
DNA 444
12.3
Reductive Electron Transfer and Excess Electron Transport
in
DNA 446
12.3.1
Strategies for the Synthesis of
DNA
Donor-Acceptor Systems
446
12.3.2
Chromophore Functionalization of
DNA
Bases via Synthesis
of
DNA
Building Blocks
448
12.3.3 DNA
Base Modifications via a Solid-phase Synthetic Strategy
452
12.3.4
Chromophores as Artificial
DNA
Base Substitutes
454
12.4
Results from the Electron Transfer Studies
456
12.5
Outlook: Towards Synthetic Nanostructures Based
on DNA-like Architecture
460
References
463
13
Electron Transfer of ^-Functional Systems and Applications
465
Shunichi Fukuzumi
13.1
Introduction
465
13.2
Efficient Electron-transfer Properties of Zinc Porphyrins
467
13.3
Efficient Electron-transfer Properties of Fullerenes
474
13.4
Photoinduced Electron Transfer in Electron Donor-Acceptor
Linked Molecules Mimicking the Photosynthetic Reaction Center
477
13.5
An Orthogonal
π
-Donor-
Acceptor Dyad Affording
an Infinite CS Lifetime
485
13.6
A Long-lived
ET
State Acting as an Efficient
ET Photocatalyst 490
13.7
Organic Solar Cells Using Simple Donor-Acceptor Dyads
494
13.8
Organic Solar Cells Composed of Multi-porphyrin/Qo
Supramolecular Assemblies
499
13.9
Conclusion
506
Acknowledgments
506
References
507
14
Induced Jt-Stacking in
Acenes
511
John E. Anthony
14.1
Introduction
52 2
14.2
Anthracene
522
14.2.1
Monosubstituted Anthracene
514
14.2.2
Disubstituted Anthracene
517
14.2.3
Edge-substituted Anthracenes
(Anthracene Functionalized at the
1,8-
or 1,8,9-Positions)
522
XII Contents
14.2.4 Liquid
Crystalline Anthracenes
525
14.2.5
Anthracene Self-assembly: Hydrogen Bonding
526
14.3
Tetracene (Naphthacene)
528
14.3.1
Ethynyltetracenes
530
14.3.2
Tetrasubstituted Tetracenes
532
14.4
Pentacene
534
14.5
Higher
Acenes
540
14.6
Conclusion
541
Acknowledgments
542
References
542
15
Synthesis and Characterization of Novel Chiral Conjugated Materials
547
Andrzej Rajca
and Makoto Miyasaka
15.1
Introduction
547
15.2
Synthetic Approaches to Highly Annelated Chiral
π
-Conjugated
Systems
548
15.2.1
Helicenes
548
15.2.1.1
Photochemical Syntheses
549
15.2.1.2
Non-photochemical Syntheses
551
15.2.2
Double Helicenes and Chiral Polycyclic Aromatic Hydrocarbons
560
15.2.3
Tetraphenylenes and
π
-Conjugated
Double Helices
563
15.3
Barriers for Racemization of Chiral
π
-Conjugated
Systems
567
15.4
Strong Chiroptical Properties in Absorption,
Emission and Refraction
570
15.4.1
Absorption and Emission
570
15.4.2
Refraction
572
15.5
Conclusion
574
Acknowledgments
574
References
574
Index
583 |
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| id | DE-604.BV021838706 |
| illustrated | Illustrated |
| index_date | 2024-07-02T15:59:43Z |
| indexdate | 2024-07-20T09:09:42Z |
| institution | BVB |
| isbn | 9783527313020 3527313028 |
| language | English |
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| spelling | Functional organic materials syntheses, strategies and applications ed. by Thomas J. J. Müller ... Weinheim Wiley-VCH 2007 XX, 591 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Compuestos orgánicos Makromolekulare Chemie (DE-588)4168684-6 gnd rswk-swf Organischer Stoff (DE-588)4203832-7 gnd rswk-swf Makromolekulare Chemie (DE-588)4168684-6 s Organischer Stoff (DE-588)4203832-7 s DE-604 Müller, Thomas J. J. Sonstige (DE-588)11370979X oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2831372&prov=M&dok_var=1&dok_ext=htm Inhaltstext Digitalisierung UB Augsburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015050583&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Functional organic materials syntheses, strategies and applications Compuestos orgánicos Makromolekulare Chemie (DE-588)4168684-6 gnd Organischer Stoff (DE-588)4203832-7 gnd |
| subject_GND | (DE-588)4168684-6 (DE-588)4203832-7 |
| title | Functional organic materials syntheses, strategies and applications |
| title_auth | Functional organic materials syntheses, strategies and applications |
| title_exact_search | Functional organic materials syntheses, strategies and applications |
| title_exact_search_txtP | Functional organic materials syntheses, strategies and applications |
| title_full | Functional organic materials syntheses, strategies and applications ed. by Thomas J. J. Müller ... |
| title_fullStr | Functional organic materials syntheses, strategies and applications ed. by Thomas J. J. Müller ... |
| title_full_unstemmed | Functional organic materials syntheses, strategies and applications ed. by Thomas J. J. Müller ... |
| title_short | Functional organic materials |
| title_sort | functional organic materials syntheses strategies and applications |
| title_sub | syntheses, strategies and applications |
| topic | Compuestos orgánicos Makromolekulare Chemie (DE-588)4168684-6 gnd Organischer Stoff (DE-588)4203832-7 gnd |
| topic_facet | Compuestos orgánicos Makromolekulare Chemie Organischer Stoff |
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