[n]cumulenes - chain elongation and studies on the rotational barrier: = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere
Gespeichert in:
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| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
Erlangen ; Nürnberg
[2017]
|
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| Online-Zugang: | Inhaltsverzeichnis Inhaltsverzeichnis |
| Beschreibung: | XVI, 253 Seiten Illustrationen, Diagramme 21 cm |
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| 245 | 1 | 0 | |a [n]cumulenes - chain elongation and studies on the rotational barrier |b = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |c vorgelegt von Martina Ursula Bühringer |
| 246 | 1 | 3 | |a [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| 246 | 1 | 1 | |a [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| 264 | 1 | |a Erlangen ; Nürnberg |c [2017] | |
| 300 | |a XVI, 253 Seiten |b Illustrationen, Diagramme |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |b Dissertation |c Friedrich-Alexander-Universität Erlangen-Nürnberg |d 2017 | ||
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Datensatz im Suchindex
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|---|---|
| adam_text | TABLE OF CONTENT
LIST OF ABBREVIATIONS AND
SYMBOLS......................................................................................VII
ABSTRACT.....................................................................................................................................
XIII
KURZZUSAMMENFASSUNG..........................................................................................................
XV
1 GENERAL INTRODUCTION TO
CUMULENES................................................................................1
1.1 CARBON-RICH
COMPOUNDS.............................................................................................1
1.2 CLASSIFICATION AND HISTORY OF ALLENES AND [NJCUMULENES
...........................................
3
1.3 COMMON SYNTHETIC ROUTES TO ALLENES AND [NJCUMULENES
........................................
5
1.4 REACTIVITY OF
[NJCUMULENES...........................................................................................7
1.5 PROPERTIES OF
[NJCUMULENES........................................................................................10
1.5.1 STRUCTURAL FEATURES FROM X-RAY CRYSTALLOGRAPHIC
ANALYSIS...............................10
1.5.2 ELECTRONIC PROPERTIES OF [NJCUMULENES
...................................................
13
1.5.2.1 UV-VIS
SPECTROSCOPY....................................................................................13
1.5.2.2 ELECTROCHEMISTRY
...........................................................................................
15
1.5.3 STEREOISOMERISM AND ROTATIONAL BARRIERS
.........................................................
18
1.6 MOTIVATION AND GOALS OF THE THESIS
...........................................................................
22
1.6.1 EVEN-NUMBERED SYMMETRICALLY SUBSTITUTED
[NJCUMULENES.............................23
1.6.2 ODD-NUMBERED UNSYMMETRICALLY SUBSTITUTED [NJCUMULENES
..........................
24
1.7
REFERENCES...................................................................................................................
26
2 EVEN-NUMBERED
TETRAARYL[N]CUMULENES.......................................................................33
2.1 O
VERVIEW......................................................................................................................33
2.2
MOTIVATION.....................................................................................................................33
2.3 SYNTHESIS OF EVEN-NUMBERED [N]FBUPH
CUMULENES..............................................34
2.3.1 SYNTHESIS OF THE ENDGROUP
.................................................................................
34
2.3.2 SYNTHESIS OF ALLENE [2]FBUPH
2.3.3 SYNTHESIS OF [4]CUMULENE [4]FBUPH
.................................................................
36
2.3.4 SYNTHESIS OF [6]CUMULENE [6]FBUPH
.................................................................
36
2.4 CHARACTERIZATION OF EVEN-NUMBERED [NJFFIUPH
CUMULENES....................................42
2.4.1 SOLID-STATE ANALYSIS OF
[4]FBUPH........................................................................42
2.4.2 OPTOELECTRONIC
PROPERTIES....................................................................................
46
2.4.2 CYCLIC
VOLTAMMETRY..............................................................................................49
2.4.3
STABILITY..................................................................................................................
51
2.5 SUMMARY AND
CONCLUSIONS.........................................................................................52
2.6
REFERENCES...................................................................................................................
52
SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ODD-NUMBERED TETRAARYL-
[N]CUMULENES.....................................................................................................................55
3.1
OVERVIEW......................................................................................................................
55
3.2 SYNTHESIS OF [N]TRTOL
SERIES.....................................................................................
56
3.2.1 SYNTHESIS OF THE
ENDGROUP..................................................................................56
3.2.2 SYNTHESIS OF THE [N]TRTOL
CUMULENES...............................................................
57
3.2.2.1 SYNTHESIS OF
[3]TRTOL....................................................................................
57
3.2.2 2 SYNTHESIS OF
[5]TRTOL....................................................................................
58
3.2.2.3 SYNTHESIS OF
[7]TRTOL....................................................................................
59
3.2.2.4 SYNTHESIS OF
[9]TRTOL...................................................................................61
3.2.2.5 SYNTHESIS OF
[11]TRTOL..................................................................................62
3.2 2.6 SYNTHESIS OF
[13]TRTOL..................................................................................64
3.3 SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED
TETRAARYL[5]CUMULENES..........................66
3.3.1 SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED KETONES AS ENDCAP FOR
T ETRAARY
L[5]CUMULENES..........................................................................................67
3.3.2 SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED TETRAARYL[5]CUMULENES
................
67
3.4 SUMMARY AND CONCLUSIONS
........................................................................................
70
3.5
REFERENCES...................................................................................................................70
4 X-RAY C RYSTALLOGRAPHIC ANALYSIS O F U NSYM M ETRICALLY S UBSTITUTED
TETRAARYL-
[N]CU M U LE N E
S.....................................................................................................................73
4.1 O
VERVIEW......................................................................................................................73
4.2 SOLID-STATE PROPERTIES OF
[N]CUMULENES....................................................................73
4.2.1 SOLID-STATE ANALYSIS OF [3]T RT
OL..........................................................................74
4.2.2 SOLID-STATE ANALYSIS OF
[5]CUMULENES................................................................75
4.2.2.1
[5]TRTOL.........................................................................................................
75
4.2.22 [5]TOLP
H.........................................................................................................76
4.2.2.3
[5]FPHPH........................................................................................................
78
4.3 COMPARISON OF THE STRUCTURAL
PROPERTIES..................................................................79
4.4 SUMMARY AND
CONCLUSIONS........................................................................................81
4.5
REFERENCES...................................................................................................................61
5 DETERMINATION O F THE ROTATIONAL B A
RRIER......................................................................83
5.1 INTRODUCTION AND
THEORY...............................................................................................63
5.1.1 COMPLETE LINE SHAPE
ANALYSIS...........................................................................64
5.1.2 APPROXIMATION
EQUATIONS.....................................................................................86
5.1.3 ESTIMATING THE
ERROR.............................................................................................
67
5.2 O
VERVIEW......................................................................................................................67
5.3 ROTATIONAL BARRIER AS A FUNCTION OF CHAIN
LENGTH.....................................................88
5.3.1 EXPERIMENTAL DETERMINATION OF THE ROTATIONAL BARRIER BY DYNAMIC
NMR
SPECTROSCOPY........................................................................................................
66
5.3.2 THEORETICAL CALCULATIONS OF THE ROTATIONAL BARRIER IN [NJCUMULENES
..............
94
5.4 INFLUENCE OF SUBSTITUTION OF PHENYL RINGS ON THE BARRIER TO ROTATION
.....................
96
5.4.1 EXPERIMENTAL ANALYSIS OF THE ROTATIONAL BARRIERS BY DYNAMIC NMR
SPECTROSCOPY........................................................................................................
96
5.4.2 COMPARISON BETWEEN EXPERIMENTAL AND THEORETICAL DETERMINED
ROTATIONAL
BARRIERS..................................................................................................................
99
5.5 SUMMARY AND
CONCLUSIONS......................................................................................100
5.6
REFERENCES.................................................................................................................101
6 OPTOELECTRONIC AND ELECTROCHEMICAL PROPERTIES OF UNSYMMETRICALLY
SUBSTITUTED
ODD-NUMBERED
TETRAARYL[/I]CUMULENES......................................................................
103
6.1
OVERVIEW.....................................................................................................................103
6.2 OPTOELECTRONIC AND ELECTROCHEMICAL PROPERTIES AS A FUNCTION OF
CUMULENE
CHAIN
LENGTH..............................................................................................................104
6.2.1 OPTOELECTRONIC PROPERTIES AS A FUNCTION OF CHAIN
LENGTH............................104
6.2.2 REDOX BEHAVIOR OF [N]CUMULENES AS A FUNCTION OF CHAIN LENGTH
..............
108
6.2.3 COMPARISON OF THE OPTOELECTRONIC, ELECTRONIC, AND CALCULATED
HOMO-LUMO
GAPS...........................................................................................110
6.3 INFLUENCE OF THE ENDGROUP ON THE OPTOELECTRONIC AND ELECTROCHEMICAL
PROPERTIES...................................................................................................................
112
6.3.1 INFLUENCE OF THE ENDGROUP ON OPTOELECTRONIC
PROPERTIES...............................112
6.3.2 INFLUENCE OF THE ENDGROUP ON THE REDOX BEHAVIOUR OF
[5]CUMULENES.......114
6.3.3 COMPARISON OF THE OPTOELECTRONIC, ELECTRONIC, AND CALCULATED
HOMO-LUMO
GAPS...........................................................................................
118
6.4 SUMMARY AND
CONCLUSIONS.......................................................................................119
6.5
REFERENCES.................................................................................................................
120
7 SUMMARY AND
OUTLOOK...................................................................................................123
7.1 EVEN-NUMBERED SYMMETRICALLY SUBSTITUTED [NJCUMULENES
.................................
123
7.2 ODD-NUMBERED UNSYMMETRICALLY SUBSTITUTED [N]CUMULENES
...............................
125
7.3
REFERENCES.................................................................................................................
128
8 EXPERIMENTAL
SECTION.....................................................................................................
129
6.1 GENERAL PROCEDURES AND METHODS
..........................................................................
129
8.2 EXPERIMENTAL DATA AND COMPOUND CHARACTERIZATION
...........................................
131
6.2.1 SYNTHESIS OF KNOWN
COMPOUNDS.....................................................................131
6.2.2 SYNTHETIC PROTOCOLS OF NEW
COMPOUNDS.........................................................134
8.2.2.1 EVEN-NUMBERED SYMMETRICALLY SUBSTITUTED [N]CUMULENES
...................
134
5.2.2.2 ODD-NUMBERED UNSYMMETRICALLY SUBSTITUTED [NJCUMULENES
.................
144
8.3 SPECTRA
APPENDIX......................................................................................................177
8.3.1 1H, 13C, AND 19F NMR
SPECTRA...........................................................................177
8.3.2 DSC
SCANS..........................................................................................................237
6.3.3 1H NMR SPECTRA OF THE
CIS-TRANS
ISOMERIZATION OF [3]TRTOL
.........................
243
8.3.4 TEMPERATURE-DEPENDENT NMR SPECTRA
...........................................................
244
8.3.4.1 [N]TRTOL
SERIES...........................................................................................
244
5.3.4.2 UNSYMMETRICALLY SUBSTITUTED
[5]CUMULENES............................................246
8.4
REFERENCES................................................................................................................
253
|
| any_adam_object | 1 |
| author | Bühringer, Martina Ursula |
| author_facet | Bühringer, Martina Ursula |
| author_role | aut |
| author_sort | Bühringer, Martina Ursula |
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| indexdate | 2024-07-10T08:03:13Z |
| institution | BVB |
| language | English |
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| spelling | Bühringer, Martina Ursula Verfasser aut [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere vorgelegt von Martina Ursula Bühringer [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere Erlangen ; Nürnberg [2017] XVI, 253 Seiten Illustrationen, Diagramme 21 cm txt rdacontent n rdamedia nc rdacarrier Dissertation Friedrich-Alexander-Universität Erlangen-Nürnberg 2017 Kumulene (DE-588)4166000-6 gnd rswk-swf Innere Rotation (DE-588)4161807-5 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Kumulene (DE-588)4166000-6 s Innere Rotation (DE-588)4161807-5 s DE-604 B:DE-101 application/pdf http://d-nb.info/1152099027/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030259225&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bühringer, Martina Ursula [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere Kumulene (DE-588)4166000-6 gnd Innere Rotation (DE-588)4161807-5 gnd |
| subject_GND | (DE-588)4166000-6 (DE-588)4161807-5 (DE-588)4113937-9 |
| title | [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| title_alt | [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| title_auth | [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| title_exact_search | [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| title_full | [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere vorgelegt von Martina Ursula Bühringer |
| title_fullStr | [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere vorgelegt von Martina Ursula Bühringer |
| title_full_unstemmed | [n]cumulenes - chain elongation and studies on the rotational barrier = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere vorgelegt von Martina Ursula Bühringer |
| title_short | [n]cumulenes - chain elongation and studies on the rotational barrier |
| title_sort | n cumulenes chain elongation and studies on the rotational barrier n kumulene kettenverlangerung und studien zur bestimmung der rotationsbarriere |
| title_sub | = [n]Kumulene - Kettenverlängerung und Studien zur Bestimmung der Rotationsbarriere |
| topic | Kumulene (DE-588)4166000-6 gnd Innere Rotation (DE-588)4161807-5 gnd |
| topic_facet | Kumulene Innere Rotation Hochschulschrift |
| url | http://d-nb.info/1152099027/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030259225&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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