Synthesis and second-order nonlinear optical properties of push-pull BODIPY derivatives

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Wen-Jing Shi
  • Pui-Chi Lo
  • Anu Singh
  • Isabelle Ledoux-Rak
  • Dennis K.P. Ng

Detail(s)

Original languageEnglish
Pages (from-to)8712-8718
Journal / PublicationTetrahedron
Volume68
Issue number42
Publication statusPublished - 21 Oct 2012
Externally publishedYes

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 CH 2Cl 2. 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 CHCl 3. 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. © 2012 Elsevier Ltd. All rights reserved.

Research Area(s)

  • Boron dipyrromethene, Cross-coupling, Donor-acceptor systems, Nonlinear optics, Push-pull chromophores

Citation Format(s)

Synthesis and second-order nonlinear optical properties of push-pull BODIPY derivatives. / Shi, Wen-Jing; Lo, Pui-Chi; Singh, Anu; Ledoux-Rak, Isabelle; Ng, Dennis K.P.

In: Tetrahedron, Vol. 68, No. 42, 21.10.2012, p. 8712-8718.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review