Hydrogen bond-directed self-assembly of perylene bisimide organogelators [Elektronische Ressource] / vorgelegt von Xueqing Li

Li Xueqing

Sujets

• Naturwissenschaften

Informations

• Publié par: julius-maximilians-universitat_wurzburg
• Publié le: 01 janvier 2009
• Nombre de lectures: 20
• Poids de l'ouvrage: 18 Mo

Extrait

Hydrogen Bond-directed
Self-assembly of Perylene Bisimide
Organogelators




Dissertation zur Erlangung des
naturwissenschaftlichen Doktorgrades
der Julius-Maximilians-Universität Würzburg



vorgelegt von
Xueqing Li
aus Dezhou, China


Würzburg 2009













Eingereicht am:
bei der Fakultät für Chemie und Pharmazie

1. Gutachter: Prof. Dr. Frank Würthner
2. Gutachter:
der Dissertation

1. Prüfer: Prof. Dr. Frank Würthner
2. Prüfer:
3. Prüfer:
des öffentlichen Promotionscolloquiums

Tag des öffentlichen Promotionscolloquiums:
Doktorurkunde ausgehändigt am: ___________________________




für meine Familie
List of Abbreviations

AFM atomic force microscope
ACW anti-clockwise
CD circular dichroism
CGC critical gelation concentration
CW clockwise
DMF N,N-dimethylformamide
DSC differential scanning calorimetry
ESI electrospray ionization
HOPG highly ordered pyrolytic graphite
LD linear dichroism
LC liquid crystal / liquid crystalline
LMOG low molecular-mass organogelator
MCH methylcyclohexane
MALDI-TOF matrix-assisted laser desorption injection time-of-flight
NMR nuclear magnetic resonance
NRs nanorods
PBI perylene-3,4:9,10-tetracarboxylic acid bisimide
PR-TRMC pulse-radiolysis time-resolved microwave conductivity
OPM optical polarized microscopy
OPV oligo-p-phenylene-vinylene
SEM scanning electron microscope
STM scanning tunneling microscope
THF tetrahydrofuran
TMS tetramethylsilane
TEM transmission electron microscope
UV-vis ultraviolet-visible Table of Contents

Chapter 1 Introduction and Aim of this Thesis……………………………........1

Chapter 2 State of Knowledge…………………………………...……………….7
2.1 Structural and functional features of organogel systems………………....7
2.1.1 Definition and principles…………………………………………….7
2.1.2 Reversibility of organogels………………………… ………...…….9
2.2 Dye based organogelators…………..……………………………........16
2.3 Supramolecular chirality……………….…………………………..….23
2.3.1 Characterization of supramolecular chirality…………………........24
In solution………………………………………………………….24
In solid state……………………………………………………......26
2.3.2 Amplification and formation of homochiral aggregates..………….28
Chirality amplification……………………………………...……...28
Formation of hom ochiral aggregates by symmetry breaking……...30
Macroscopic alignment…………………………………………….33
2.4 References and notes…………….…………………………………….35

Chapter 3 Functional Organogels from Highly Efficient Organogelator
based on Perylene Bisimides…….................………………….............41
3.1 Introduction............................................................................................41
3.2 Results and discussions…………………………………………..........42
3.2.1 Synthesis and gelation test…………………………………………42
3.2.2 Spectroscopic characterization…………………………...………...43
3.2.3 Microscopic studies...........................................................................46
3.2.4 Thermal behavior..............................................................................49
3.2.5 Charge carrier mobility......................................................................51 3.3 Summary.................................................................................................52
3.4 Experimental details...............................................................................47
3.5 References and notes.............................................................................55

Chapter 4 Recognition of Micro- and Macroscopic Chiral
Assembly in Non-Equilibrium Environments...................................59
4.1 Introduction............................................................................................59
4.2 Structural features and aggregation behaviors.......................................61
4.3 Change of helical bias by chiral solvents...............................................66
4.3.1 CD-spectroscopic monitori ng of chiral assembly.............................66
4.3.2 Morphology of the chiral aggregates................................................70
4.4 Macroscopic alignment of the aggregates in vortex flow......................72
4.5 Conclusions……………………………………………………………79
4.6 Experimental details…………………………………………………...80
4.7 References and notes..............................................................................81

Chapter 5 Highly Fluorescen t Mesophases and Organogels Based on
J-Aggregates of Core-Twisted Perylene Bisimide Dyes ...................85
5.1 Introduction............................................................................................85
5.2 Results and discussions………………………………………………..86
5.2.1 Structural properties..........................................................................86
5.2.2 Organogels and mesophases.............................................................88
5.2.3 Spectroscopic properties...................................................................91
5.2.4 Microscopic morphology..................................................................95
5.2.5 Calculation of excitonic coupling and the models............................97
5.2.6 Light emission ability........................................................................99
5.3 Conclusion............................................................................................100
5.4 Experimental details.............................................................................101
5.5 References and notes…………………………………………………103