Organization of a New Tetraalkynyl Porphyrin by the Langmuir−Blodgett Technique

A new tetraalkynyl porphyrin: the meso-tetra(trimethylsilylethynyl)-β-tetra(acetic acid)porphyrin, abbreviated as H2P1, has been synthesized and organized by the Langmuir−Blodgett technique. When spread alone on pure water, it spontaneously stacks in a herringbone manner. Different methods have been...

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Veröffentlicht in:Langmuir 1999-05, Vol.15 (10), p.3653-3660
Hauptverfasser: Da Cruz, Fernande, Armand, Franck, Albouy, Pierre-Antoine, Nierlich, Martine, Ruaudel-Teixier, Annie
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Sprache:eng
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Zusammenfassung:A new tetraalkynyl porphyrin: the meso-tetra(trimethylsilylethynyl)-β-tetra(acetic acid)porphyrin, abbreviated as H2P1, has been synthesized and organized by the Langmuir−Blodgett technique. When spread alone on pure water, it spontaneously stacks in a herringbone manner. Different methods have been used to break the π−π interactions and favor a flat-on anchoring of the macrocycle onto the water surface. Stable Langmuir and Langmuir−Blodgett films have been thus obtained and characterized by UV and IR spectroscopies and X-ray diffraction. A first method consists in introducing divalent cations into the subphase. It leads to an almost planar arrangement with a tilt angle of the macrocycle of ca. 15°. Another approach consisting in mixing a H2P1/tricosylamine complex with methyl eicosanoate was also tried. An optimal proportion of 1:4:10 was found, leading to a tilt angle of ca. 25°.
ISSN:0743-7463
1520-5827
DOI:10.1021/la981663l