Second-order optical nonlinearities and photostabilities of 2-N-methylstilbazolium salts

Creators: Marder, Seth R.; Perry, Joseph W.; Tiemann, Bruce G.; Marsh, Richard E.; Schaefer, William P.

Abstract

We have synthesized a number of 2-N-methylstilbazolium salts and measured their powder second harmonic generation (SHG) efficiencies. The pale yellow salt 3'-methoxy-2-N-methylstilbazolium triflate was found to exhibit an SHG efficiency 24 times that of a urea reference standard at 532 nm, and an X-ray diffraction study showed the crystals to be noncentrosymmetric (space group Cc; a = 18.126 (4) Å, b = 7.040 (1) Å, c = 13.315 (2) Å, β = 93.46 (1)°, Z = 4). These crystals are photochemically stable under visible irradiation. On the other hand, 2'-methoxy-2-N-methylstilbazolium triiflate shows no SHG signal; it forms centrosymmetric crystals (space group P2_1/n; a = 11.999 (2) Å, b = 13.458 (2) Å, c = 11.043 (2) A, β = 108.47 (1)°, Z = 4) that undergo photochemical 2 + 2 cycloaddition.

Additional Information

© 1990 American Chemical Society. Received April 17, 1990. The research described in this paper was performed by the Jet Propulsion Laboratory, California Institute of Technology, as part of its Center for Space Microelectronics Technology, which is supported by the Strategic Defense Initiative Organization, Innovative Science and Technology Office, through an agreement with the National Aeronautics and Space Administration. S.R.M. thanks Professor Robert Grubbs for access to synthetic facilities at Caltech. The diffractometer used in this study was purchased with a grant from the National Science Foundation (CHE-8219039). We thank Paul Groves and Kelly Perry for technical assistance.

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