Supramolecular synthesis via integrative self-sorting:
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2010
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | 248 S. graph. Darst. 21 cm |
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Datensatz im Suchindex
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| adam_text | IMAGE 1
FREIE UNIVERSITAET
SUPRAMOLECULAR SYNTHESIS VIA
INTEGRATIVE SELF-SORTING
DISSERTATION ZUR ERLANGUNG DES AKADEMISCHEN GRADES DES DOKTORS DER
NATURWISSENSCHAFTEN
(DR. RER. NAT.)
EINGEREICHT IM FACHBEREICH BIOLOGIE, CHEMIE UND PHARMAZIE
DER FREIEN UNIVERSITAET BERLIN
VORGELEGT VON
WEI JIANG
AUS HENAN, V. R. CHINA
JULI, 2010
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1008084042
DIGITALISIERT DURCH
IMAGE 2
TABLE OF CONTENTS
1. INTRODUCTION: SUPRAMOLECULAR SYNTHESIS AND SELF-SORTING 17
1. 1 SUPRAMOLECULAR SYNTHESIS 17
1.2 CENTRAL ASPECTS OF SUPRAMOLECULAR SYNTHESIS 19
1.2.1 REVERSIBLE BONDS/INTERACTIONS 19
1.2.2 HOST-GUEST CHEMISTRY 22
1.2.2.1 DESIGN PRINCIPLES OF HOST MOLECULES 22
1.2.2.2 CLASSIC HOST AND GUEST MOLECULES 24
1.2.3 SUPRAMOLECULAR SYNTHONS 26
1.2.3.1 THREADED SYNTHONS 26
1.2.3.2 NON-THREADED SYNTHONS 28
1.2.4 CONSTRUCTION STRATEGIES FOR SUPRAMOLECULAR SYNTHESIS 30
1.2.4.1 SELF-ASSEMBLY 30
1.2.4.2 MULTIVALENCY AND COOPERATIVITY 31
1.2.4.3 TEMPLATE EFFECTS 36
1.2.5 SUPRAMOLECULAR KINETICS 39
1.2.6 STRUCTURAL ASPECTS OF SUPRAMOLECULES 41
1.2.7 SUPRAMOLECULAR FUNCTIONS 44
1.2.8 STRUCTURAL CHARACTERIZATION 46
1.2.8.1 X-RAY CRYSTALLOGRAPHY 47
1.2.8.2 NMR SPECTROSCOPY 48
1.2.8.3 MASS SPECTROMETRY 49
1.3 SELF-SORTING 55
1.3.1 BACKGROUND 55
1.3.1 SELF-SORTING: HISTORY, DEFINITION, AND CLASSIFICATION 55
1.3.2 THERMODYNAMIC SELF-SORTING 57
1.3.3 KINETIC SELF-SORTING 58
1.3.4 SELF-SORTING: ONE WELL-DEFINED ASSEMBLY 59
X L LL
IMAGE 3
2. RESEARCH GOALS 60
3. INTEGRATIVE SELF-SORTING 62
3.1 TEMPLATED VERSUS NON-TEMPLATED SYNTHESIS OF BENZO-21-CROWN-7 AND
THE INFLUENCE OF SUBSTITUENTS ON ITS COMPLEXING PROPERTIES 62
3.1.1 BACKGROUND 62
3.1.2 SYNTHESIS OF C7 63
3.1.3 CHARACTERIZATION OF HIGHER CROWN OLIGOMERS 2-(N) 65
3.1.4 CHARACTERIZATION OF (C7+KPF 6) FORMED IN THE KPF6-TEMPLATED
SYNTHESIS OF C7 67
3.1.5 THE EFFECT OF SUBSTITUENTS ON BINDING AFFINITY AND BINDING MODE 70
3.1.6 CONCLUSIONS 72
3.2 INTEGRATIVE SELF-SORTING: CONSTRUCTION OF A CASCADE-STOPPERED
HETERO[3]ROTAXANE 73
3.2.1 BACKGROUND 73
3.2.2 A FOUR-COMPONENT SELF-SORTING SYSTEM 73
3.2.3 A SEQUENCE-SPECIFIC HETERO[3]PSEUDOROTAXANE 74
3.2.4 A CASCADE-STOPPERED HETERO[3]ROTAXANE 77
3.2.5 CONCLUSIONS 81
3.3 INTEGRATIVE SELF-SORTING: A PROGRAMMING LANGUAGE FOR HIGH LEVEL
SELF-ASSEMBLY 82
3.3.1 BACKGROUND 82
3.3.2 DESIGN CONCEPT 83
3.3.3 MERGING TWO MONOTOPIC AXLES INTO DITOPIC ONES 85
3.3.4 MERGING TWO MONOTOPIC WHEELS INTO A HETERODITOPIC ONE 89
3.3.5 COMBINATION/REPETITION OF INTEGRATIVE SELF-SORTING STRATEGIES 91
3.3.6 CONCLUSIONS 97
4. MASS SPECTROMETRIC ANALYSIS OF SELF-SORTED PSEUDOROTAXANES 98
4. 1 TANDEM MASS SPECTROMETRY FOR THE ANALYSIS OF SELF-SORTED
PSEUDOROTAXANES: THE EFFECTS OF COULOMB INTERACTIONS 98
4.1.1 BACKGROUND 98
XIV
IMAGE 4
4.1.2 COULOMB INTERACTIONS IN SIMPLIFIED MODEL COMPLEXES 101
4.1.3 ION GENERATION 103
4.1.4 THE ROLE OF THE COUNTERION IN SINGLY CHARGED COMPLEXES 104
4.1.5 DOUBLY CHARGED FREE AMMONIUM GUESTS 107
4.1.6 DOUBLY CHARGED [3]PSEUDOROTAXANES 108
4.1.7 LARGER SELF-SORTED ASSEMBLIES 115
4.1.8 CONCLUSIONS 117
4.2 MONITORING SELF-SORTING BY ELECTROSPRAY IONIZATION MASS
SPECTROMETRY:
FORMATION INTERMEDIATES AND ERROR-CORRECTION DURING THE SELF- ASSEMBLY
OF MULTIPLY THREADED PSEUDOROTAXANES 119
4.2.1 BACKGROUND 119
4.2.2 SIMPLE BINARY PSEUDOROTAXANES 121
4.2.3 ESI-FTICR MS AS A TOOL TO STUDY SELF-SORTING PROCESSES 123
4.2.4 A FOUR-COMPONENT SELF-SORTING SYSTEM 126
4.2.5 A SEQUENCE-SPECIFIC HETERO[3]PSEUDOROTAXANE 127
4.2.6 PSEUDOROTAXANES FROM MONOTOPIC AXLES AND A HETERODITOPIC HOST 131
4.2.7 MULTIPLY THREADED PSEUDOROTAXANES 134
4.2.8 CONCLUSIONS 138
5. SELF-SORTING IN WATER 141
5.1 A WATER-SOLUBLE HETERO[3]PSEUDOROTAXANE 141
5.1.1 BACKGROUND 141
5.1.2 RESULTS AND DISCUSSION 142
5.1.3 CONCLUSIONS 149
5.2 MASS SPECTROMETRIC ANALYSIS OF WATER-SOLUBLE PSEUDOROTAXANES 151
5.2.1 BACKGROUND 151
5.2.2 ESI-FTICR MS RESULTS 152
5.2.3 DILUTION KINETICS FOLLOWED BY ESI-MS 154
5.2.4 CONCLUSIONS 158
6. THE MARRIAGE OF SELF-SORTING AND MULTIVALENCY 159
6.1 A CASCADE-STOPPERED [C2]DAISY CHAIN 159
XV
IMAGE 5
6.1.1 BACKGROUND 159
6.1.2 RESULTS AND DISCUSSION 160
6.1.3 CONCLUSIONS 164
6.2 MULTIVALENT COMPLEXES 165
6.2.1 BACKGROUND 165
6.2.2 ANOTHER [4]PSEUDOROTAXANE 165
6.2.3 THE EFFECT OF SPACERS ON HOMOMULTIVALENCY 167
6.2.4 CONCLUSIONS 170
6.3 HETEROMULTIVALENCY: DIRECTIONALLY THREADED COMPLEXES 171
6.3.1 BACKGROUND 171
6.3.2 RESULTS AND DISCUSSION 171
6.3.3 CONCLUSIONS 180
6.4 GAS-PHASE CHEMISTRY OF (PSEUDO)ROTAXANES CONTAINING
PHOTOOXYGENATED ANTHRACENE 181
6.4.1 BACKGROUND 181
6.4.2 RESULTS AND DISCUSSION 182
6.4.3 CONCLUSIONS 187
6.5 SYNTHESIS OF HETEROTRITOPIC COMPONENTS 188
7. EXPERIMENTAL SECTION 189
7.1 REAGENTS AND SOLVENTS 189
7.2 CHROMATOGRAPHY 189
7.3 NMR SPECTROSCOPY 189
7.4 MELTING POINTS 189
7.5 MASS SPECTROMETRY 189
7.6 SYNTHETIC PROCEDURES 190
8. OUTLOOK 224
9. REFERENCES 226
10. LIST OF ABBREVIATIONS 241
11. CURRICULUM VITAE 244
12. ACKNOWLEDGEMENT 247
XVI
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| any_adam_object | 1 |
| author | Jiang, Wei 1981- |
| author_GND | (DE-588)142714151 |
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| dewey-search | 547.1226 |
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| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Thesis Book |
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| spelling | Jiang, Wei 1981- Verfasser (DE-588)142714151 aut Supramolecular synthesis via integrative self-sorting vorgelegt von Wei Jiang 2010 248 S. graph. Darst. 21 cm txt rdacontent n rdamedia nc rdacarrier Berlin, Freie Univ., Diss., 2010 Supramolekulare Chemie (DE-588)4306141-2 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Selbstorganisation (DE-588)4126830-1 gnd rswk-swf Rotaxane (DE-588)4178513-7 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Supramolekulare Chemie (DE-588)4306141-2 s Chemische Synthese (DE-588)4133806-6 s Rotaxane (DE-588)4178513-7 s Selbstorganisation (DE-588)4126830-1 s DE-188 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=021103696&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Jiang, Wei 1981- Supramolecular synthesis via integrative self-sorting Supramolekulare Chemie (DE-588)4306141-2 gnd Chemische Synthese (DE-588)4133806-6 gnd Selbstorganisation (DE-588)4126830-1 gnd Rotaxane (DE-588)4178513-7 gnd |
| subject_GND | (DE-588)4306141-2 (DE-588)4133806-6 (DE-588)4126830-1 (DE-588)4178513-7 (DE-588)4113937-9 |
| title | Supramolecular synthesis via integrative self-sorting |
| title_auth | Supramolecular synthesis via integrative self-sorting |
| title_exact_search | Supramolecular synthesis via integrative self-sorting |
| title_full | Supramolecular synthesis via integrative self-sorting vorgelegt von Wei Jiang |
| title_fullStr | Supramolecular synthesis via integrative self-sorting vorgelegt von Wei Jiang |
| title_full_unstemmed | Supramolecular synthesis via integrative self-sorting vorgelegt von Wei Jiang |
| title_short | Supramolecular synthesis via integrative self-sorting |
| title_sort | supramolecular synthesis via integrative self sorting |
| topic | Supramolekulare Chemie (DE-588)4306141-2 gnd Chemische Synthese (DE-588)4133806-6 gnd Selbstorganisation (DE-588)4126830-1 gnd Rotaxane (DE-588)4178513-7 gnd |
| topic_facet | Supramolekulare Chemie Chemische Synthese Selbstorganisation Rotaxane Hochschulschrift |
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