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Controlling the π-Stacking Behavior of Pyrene Derivatives : Influence of H-Bonding and Steric Effects in Different States of Aggregation

Title data

Haedler, Andreas T. ; Misslitz, Holger ; Bühlmeyer, Christian ; Albuquerque, Rodrigo Q. ; Köhler, Anna ; Schmidt, Hans-Werner:
Controlling the π-Stacking Behavior of Pyrene Derivatives : Influence of H-Bonding and Steric Effects in Different States of Aggregation.
In: ChemPhysChem. Vol. 14 (2013) Issue 9 . - pp. 1818-1829.
ISSN 1439-4235
DOI: https://doi.org/10.1002/cphc.201300242

Official URL: Volltext

Project information

Project financing: Deutsche Forschungsgemeinschaft

Abstract in another language

The performance of opto-electronic devices built from low-molecular-weight dye molecules depends crucially on the stacking properties and the resulting coupling of the chromophoric systems. Herein we investigate the influence of H-bonding amide and bulky substituents on the π-stacking of pyrene-containing small molecules in dilute solution, as supramolecular aggregates, and in the solid state. A set of four pyrene derivatives was synthesized in which benzene or 4-tert-butyl benzene was linked to the pyrene unit either through an ester or an amide. All four molecules form supramolecular H-aggregates in THF solution at concentrations above 1×10−4 mol L−1. These aggregates were transferred on a solid support and crystallized. We investigate: the excimer formation rates within supramolecular aggregates; the formation of H-bonds as well as the optical changes during the transition from the amorphous to the crystalline state; and the excimer to monomer fluorescence ratio in crystalline films at low temperatures. We reveal that in solution supramolecular aggregation depends predominantly on the pyrene chromophores. In the crystalline state, however, the pyrene stacking can be controlled gradually by H-bonding and steric effects. These results are further confirmed by molecular modeling. This work bears fundamental information for tailoring the solid state of functional optoelectronic materials.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: fluorescence; kinetics; molecular modeling; photophysics; self-assembly
Institutions of the University: Faculties
Faculties > Faculty of Mathematics, Physics und Computer Science
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics > Lehrstuhl Experimentalphysik II - Optoelektronik weicher Materie
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics > Lehrstuhl Experimentalphysik II - Optoelektronik weicher Materie > Lehrstuhl Experimentalphysik II - Optoelektronik weicher Materie - Univ.-Prof. Dr. Anna Köhler
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I > Chair Macromolecular Chemistry I - Univ.-Prof. Dr. Hans-Werner Schmidt
Profile Fields
Profile Fields > Advanced Fields
Profile Fields > Advanced Fields > Polymer and Colloid Science
Profile Fields > Advanced Fields > Advanced Materials
Research Institutions
Research Institutions > Research Centres
Research Institutions > Research Centres > Bayreuth Institute of Macromolecular Research - BIMF
Research Institutions > Research Centres > Bayreuth Center for Colloids and Interfaces - BZKG
Graduate Schools
Graduate Schools > Bayreuth Graduate School of Mathematical and Natural Sciences (BayNAT)
Graduate Schools > Bayreuth Graduate School of Mathematical and Natural Sciences (BayNAT) > Photophysics of Synthetic and Biological Multichromophoric Systems
Graduate Schools > Elite Network Bavaria
Graduate Schools > Elite Network Bavaria > Macromolecular Science
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 530 Physics
500 Science > 540 Chemistry
Date Deposited: 11 Feb 2015 12:02
Last Modified: 06 Jul 2015 08:29
URI: https://eref.uni-bayreuth.de/id/eprint/6685