Synthesis and second-order nonlinear optical properties of push-pull BODIPY derivatives |
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Authors: | Wen-Jing Shi Pui-Chi Lo Anu Singh Isabelle Ledoux-Rak Dennis KP Ng |
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Institution: | 1. Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China;2. Laboratoire de Photonique Quantique et Moléculaire UMR CNRS 8537, Institut d’Alembert, ENS Cachan, 61 Aveneue du Président Wilson, 94235 Cachan, France |
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Abstract: | A series of boron dipyrromethene derivatives bearing an electron-donating 4-(dimethylamino)phenylethynyl group and an electron-withdrawing 4-nitrophenylethynyl group in the opposite 2- and 6-positions have been synthesized by Knoevenagel condensation followed by sequential Sonogashira coupling reactions. The compounds have been fully characterized with various spectroscopic methods. Their electrochemical properties have also been studied by cyclic voltammetry in CH2Cl2. It has been found that expansion of the π systems by introduction of the 4-dodecyloxystyryl or 4-(dimethylamino)phenylethynyl group results in lowering of the first oxidation potential, while the first reduction potential remains relatively unaffected. The second-order nonlinear optical properties of these compounds have also been studied by electric-field-induced second-harmonic generation method in CHCl3. The values of the dot product μ·β are in the range from 94×10?48 to 330×10?48 esu at 1907 nm, depending the substituents at the 3- and 5-positions. |
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