Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 50, Pages 18177-18185Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja908061q
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Funding
- University of Strasbourg through the European School of Polymer and Materials Chemistry (ECPM)
- Centre National de la Recherche Scientifique (CNRS) of France
- EU [EU-FP6-Marie Curie-035859 (BIMORE)]
- Italian Ministry MIUR [FIRB-RBNE033KMA, FIRB-RBIP06JWBH, FIRB RBIPO642YL]
- [248052]
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Two functional ethynyl-pyrene derivatives have been designed and synthesized by di- and tetra-substitutions of bromo pyrene derivatives with N-(4-ethynylphenyl)-3,4,5-tris(hexadecyloxy)benzamide fragments. The photoluminescence wavelength of the pyrene core can be tuned by the substitution pattern and the state of matter (solid, solution, gel, or liquid crystal). The disubstituted pyrene derivative 1 is not mesomorphic but produces robust and highly fluorescent gels in DMF, toluene, and cyclohexane. The well-defined fibers and ropes of the gel states were characterized by SEM and laser scanning confocal microscopy, and extended over several micrometers. The gels were integrated as active layers in field-effect transistors, which provided good bulk electron and hole charge mobilities as well as light emission generation. The tetra-substituted pyrene derivative is not a gelator but displays a stable liquid crystalline phase with 2D hexagonal symmetry between 20 and 200 degrees C. The pronounced luminescence properties of the mesophase allow one to observe original mesophase textures with flower-like patterns directly by fluorescence microscopy without crossed-polarizers.
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