Synthesis of Novel Rod-Shaped and Star-Shaped Fluorescent Phosphane Oxides-Nonlinear Optical Properties and Photophysical Properties

• Published in: Chemistry : a European journal Vol. 12; no. 35; pp. 9056 - 9065
• Main Authors: Ha-Thi, Minh-Huong, Souchon, Vincent, Hamdi, Abdelwaheb, Métivier, Rémi, Alain, Valérie, Nakatani, Keitaro, Lacroix, Pascal G., Genêt, Jean-Pierre, Michelet, Véronique, Leray, Isabelle
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 04-12-2006; WILEY‐VCH Verlag; Wiley-VCH Verlag
• Subjects: charge transfer; Chemical Physics; Chemical Sciences; fluorescence spectroscopy; nonlinear optics; Organic chemistry; phosphane oxide; Physics; solvatochromism; Fluorescence spectroscopy; Solvatochromism; Charge transfer; Phosphane oxide; Nonlinear optics
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200600464

The design of a new class of fluorophores is presented. Some push–pull chromophores (D–π–A) containing polyphenylethynyl units and a phosphane oxide moiety were efficiently prepared from common intermediates. Straightforward syntheses gave novel one‐armed, rod‐shaped and three‐armed, star‐shaped fluorophores. The optical properties of the resulting star‐shaped derivatives were evaluated, showed high fluorescence quantum yields, and their excitation induces very efficient charge redistribution. Moreover, thanks to their push–pull character, the molecules exhibited significant second‐order NLO properties with good transparency, up to 67⋅10−30 esu at 1907 nm, with an absorption λmax at 369 nm. The effect of the donor group and of the number of phenylethynyl arms have been studied in this work.
A new class of fluorophores: The synthesis, nonlinear optical properties, and photophysical studies of a new class of push–pull chromophores (such as depicted) are presented. These novel donor–acceptor acetylene‐bridged compounds, obtained through organophosphorus reactions and Sonogashira couplings, exhibit high fluorescence quantum yields, whilst excitation induces very efficient charge redistribution within the molecules.