High hyperpolarizabilities of donor-p-acceptor-functionalized calix[4]arene derivatives by pre-organization of chromophores

Paul J.A. Kenis, Esther G. Kerver, Bianca H.M. Snellink‐Ruël , Gerrit J. van Hummel, Sybolt Harkema, Marinus C. Flipse, Richard H. Woudenberg, Johan F.J. Engbersen, David N. Reinhoudt

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A systematic investigation of the conceptofpre-organization of nonlinear optical (NLO) active chromophoric groups in calix[4]arene derivatives and the influence on the absolute second-order nonlinear optical coefficients is reported. Several calix[4]arenes were synthesized by modification of the electron-withdrawing groups at the upper rim of the aromatic and extension of the conjugated system of the pre-organized chromophoric groups. Electrical field induced second harmonic generation (EFISH) experiments showed high (0) values up to 1165·10-48 esu. Compared with the corresponding reference compounds, enhancements of the (0) values varying up to 2.5 times per chromophore were observed which proves the benefit of pre-organization of NLO-active units in a multi-chromophoric system. Another important advantage is that the increase in NLO activity observed for these systems is not accompanied with a shift of the absorption band to longer wavelengths exceeding 20 nm. This makes these calix[4]arene derivatives promising building blocks for the development of stable, NLO-active materials that are suitable for frequency doubling.
Original languageEnglish
Pages (from-to)1089-1098
JournalEuropean journal of organic chemistry
Issue number6
Publication statusPublished - 1998


  • Pre-organization
  • Supramolecular Chemistry
  • Nonlinear optics
  • Chromophores
  • Calixarenes


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