TY  - THES
A1  - Safont Sempere, Marina Montserrat
T1  - Chiral self-sorting of atropo-enantiomeric perylene bisimide dyes
T1  - Chirale Self-sortierung von Atropo-enantiomerische Perilene Bisimide Farbstofe
N2  - This thesis included the synthesis of conformationally stable chiral perylene bisimide (PBI) dyes, the study of their optical properties in solution and their chiral self-sorting behaviour in nonpolar solvents in which dimerization via pi-pi-stacking takes place. Furthermore, the influence of PBI core chirality on the properties of these dyes in the condensed state has been also studied. We have demonstrated and quantified the prevalence of chiral self-recognition over self-discrimination in pi-stacking dimerization of PBIs. It has been shown that this self-recognition event is compromised by the increasing flexibility of the structures related to the size of the OEG bridging units. Moreover, the inherent chirality of these PBIs has been proven to strongly influence their condensed state properties, for which large differences between the pure enantiomers and the racemates were revealed, as well as between the different bridged macrocyclic PBIs.
N2  - Das Ziel der vorliegenden Arbeit war die Synthese von konformationsstabilen chiralen Perylenbisimidfarbstoffen (PBI), die Bestimmung ihrer optischen Eigenschaften in Lösung und ihrer chiralen Selbstsortierung in unpolaren Lösungsmitteln, in denen Dimerisierung durch pi-pi-Stapelung stattfindet. Des Weiteren wurde noch der Einfluss der PBI Kernchiralität auf die flüssigkristallinen Eigenschaften untersucht. Zusammenfassend konnte im Rahmen dieser Arbeit die Bevorzugung der chiralen Selbst-Erkennung gegenüber der Selbst-Diskriminierung in pi-gestapelten dimerisierten PBIs quantifiziert und bewiesen werden. Eine erhöhte Flexibilität der Moleküle durch Verlängerung der OEG Brückeneinheiten verringert jedoch die Qualität dieses Selbsterkennungsvorgangs. Des Weiteren hat die Chiralität dieser PBIs einem sehr starken Einfluss auf die Eigenschaften der kondensierten Materie, in welcher große Unterschiede für reine Enantiomere und das Racemat sowie zwischen PBIs mit unterschiedlichen Brückeneinheiten gefunden wurden.
KW  - Farbstoff
KW  - Selbstorganisation
KW  - Chiralität
KW  - Atropisomerie
KW  - Self-Sortierung
KW  - pi-pi Wechselwirkungen
KW  - Aggregation
KW  - self-sorting
KW  - chirality
KW  - pi-pi- stacking
Y1  - 2010
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-55359
ER  - 
TY  - JOUR
A1  - Rest, Christina
A1  - Mayoral, María José
A1  - Fernández, Gustavo
T1  - Aqueous Self-Sorting in Extended Supramolecular Aggregates
JF  - International Journal of Molecular Sciences
N2  - Self-organization and self-sorting processes are responsible for the regulation and control of the vast majority of biological processes that eventually sustain life on our planet. Attempts to unveil the complexity of these systems have been devoted to the investigation of the binding processes between artificial molecules, complexes or aggregates within multicomponent mixtures, which has facilitated the emergence of the field of self-sorting in the last decade. Since, artificial systems involving discrete supramolecular structures, extended supramolecular aggregates or gel-phase materials in organic solvents or—to a lesser extent—in water have been investigated. In this review, we have collected diverse strategies employed in recent years to construct extended supramolecular aggregates in water upon self-sorting of small synthetic molecules. We have made particular emphasis on co-assembly processes in binary mixtures leading to supramolecular structures of remarkable complexity and the influence of different external variables such as solvent and concentration to direct recognition or discrimination processes between these species. The comprehension of such recognition phenomena will be crucial for the organization and evolution of complex matter.
KW  - co-aggregation
KW  - self-sorting
KW  - supramolecular chemistry
KW  - self-assembly
Y1  - 2013
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-129435
VL  - 14
IS  - 1
ER  -