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

Titelangaben

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. Bd. 131 (2009) Heft 40 . - S. 14442-14453.
ISSN 1520-5126
DOI: https://doi.org/10.1021/ja905260c

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Projektfinanzierung: Andere

Abstract

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.

Weitere Angaben

Publikationsform: Artikel in einer Zeitschrift
Begutachteter Beitrag: Ja
Institutionen der Universität: Fakultäten
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Makromolekulare Chemie I
Profilfelder
Profilfelder > Emerging Fields
Profilfelder > Emerging Fields > Energieforschung und Energietechnologie
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Professur Angewandte Funktionspolymere > Professur Angewandte Funktionspolymere - Univ.-Prof. Dr. Mukundan Thelakkat
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Professur Angewandte Funktionspolymere
Titel an der UBT entstanden: Ja
Themengebiete aus DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Eingestellt am: 14 Apr 2016 08:19
Letzte Änderung: 21 Jul 2016 08:32
URI: https://eref.uni-bayreuth.de/id/eprint/1294