Title data
Wicklein, André ; Lang, Andreas ; Muth, Mathis-Andreas ; Thelakkat, Mukundan:
Swallow-Tail Substituted Liquid Crystalline Perylene Bisimides : Synthesis and Thermotropic Properties.
In: Journal of the American Chemical Society.
Vol. 131
(2009)
Issue 40
.
- pp. 14442-14453.
ISSN 1520-5126
DOI: https://doi.org/10.1021/ja905260c
Project information
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Abstract in another language
Tailor-made synthesis and structure−property relationship of several swallow-tail N-substituted perylene bisimide (PBI) dyes are presented. PBI derivatives were synthesized by two distinct synthetic approaches, the details being evaluated herein. All the PBIs carry either alkyl swallow-tail or oligoethylenglycolether (OEG) swallow-tail moieties as N-substituents, and many of them are unsymmetrically substituted. We avoided substitution at bay positions of the perylene core to maintain the planarity and strong π−π interactions, which favor intermolecular order and charge carrier transport. The thermotropic behavior, which is strongly influenced by the nature of the substituents was investigated using differential scanning calorimetry (DSC), polarization optical microscopy (POM), and X-ray diffraction measurements (XRD). The introduction of OEG swallow-tail units facilitates thermotropic liquid crystalline behavior in most cases and the unsymmetrical substitution allowed the tuning of the mesophase-width. The mesophases exhibit characteristic columnar hexagonal (Colh) packing arising from π−π interactions between cofacially orientated perylene molecules. Thus, the inherent tendency of PBI molecules for crystallization could be effectively suppressed by incorporating flexible OEG swallow-tail units only at imide positions. This molecular design was crucial to obtain liquid crystallinity and intracolumnar long-range order. The substituents did not influence the electronic energy levels such as HOMO and LUMO.
Further data
Item Type: | Article in a journal |
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Refereed: | Yes |
Institutions of the University: | Faculties 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 Profile Fields Profile Fields > Emerging Fields Profile Fields > Emerging Fields > Energy Research and Energy Technology Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Applied Functional Polymers > Professor Applied Functional Polymers - Univ.-Prof. Dr. Mukundan Thelakkat Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Applied Functional Polymers |
Result of work at the UBT: | Yes |
DDC Subjects: | 500 Science > 540 Chemistry |
Date Deposited: | 14 Apr 2016 08:19 |
Last Modified: | 21 Jul 2016 08:32 |
URI: | https://eref.uni-bayreuth.de/id/eprint/1294 |