Two-photon absorption properties of Dehydrobenzo[12]annulenes and hexakis(phenylethynyl)benzenes: effect of edge-linkage

Chemphyschem. 2007 Dec 21;8(18):2671-7. doi: 10.1002/cphc.200700555.


Two-photon absorption (TPA) properties of two trefoil-shaped compounds with different edge linkages--tris(hexadehydrotribenzo[12]annulene) and tris(tetradehydrotribenzo[12]annulene)--and three asterisk-shaped compounds having no edge-linkage--hexakis(phenylethynyl)benzenes--are investigated experimentally by the open-aperture Z-scan and TPA-induced fluorescence methods with wavelength tuneable femtosecond pulses. The compound with ethynylene edge-linkage exhibits the most intense TPA (the maximal TPA cross section is 1300+/-170 GM at 572 nm where 1 GM=10(-50) cm(4) s molecule(-1) photon(-1)). The TPA activity of the compounds is primarily explained in terms of the planarity of the molecules in relation with the type of edge-linkage.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Benzene / chemistry*
  • Benzene Derivatives / chemistry
  • Chemistry, Physical / methods*
  • Electrochemistry / methods
  • Electronics
  • Hydrocarbons
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Photons
  • Polycyclic Compounds / chemistry*
  • Spectrometry, Fluorescence / methods*
  • Time Factors


  • Alkynes
  • Benzene Derivatives
  • Hydrocarbons
  • Polycyclic Compounds
  • dehydrobenzo(12)annulene
  • Benzene