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Swallow-Tail Substituted Liquid Crystalline Perylene Bisimides : Synthesis and Thermotropic Properties

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

Project financing: Andere

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
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 > Professorship Applied Functional Polymers > Professorship Applied Functional Polymers - Univ.-Prof. Dr. Mukundan Thelakkat
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professorship 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