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Science 11 September 1998:
Vol. 281. no. 5383, pp. 1653 - 1656
DOI: 10.1126/science.281.5383.1653
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Reports

Design of Organic Molecules with Large Two-Photon Absorption Cross Sections

Marius Albota, David Beljonne, Jean-Luc Brédas, * Jeffrey E. Ehrlich, Jia-Ying Fu, Ahmed A. Heikal, Samuel E. Hess, Thierry Kogej, Michael D. Levin, Seth R. Marder, * Dianne McCord-Maughon, Joseph W. Perry, * Harald Röckel, Mariacristina Rumi, Girija Subramaniam, Watt W. Webb, * Xiang-Li Wu, Chris Xu

A strategy for the design of molecules with large two-photon absorption cross sections, delta , was developed, on the basis of the concept that symmetric charge transfer, from the ends of a conjugated system to the middle, or vice versa, upon excitation is correlated to enhanced values of delta . Synthesized bis(styryl)benzene derivatives with donor-pi -donor, donor-acceptor-donor, and acceptor-donor-acceptor structural motifs exhibit exceptionally large values of delta , up to about 400 times that of trans-stilbene. Quantum chemical calculations performed on these molecules indicate that substantial symmetric charge redistribution occurs upon excitation and provide delta  values in good agreement with experimental values. The combination of large delta  and high fluorescence quantum yield or triplet yield exhibited by molecules developed here offers potential for unprecedented brightness in two-photon fluorescent imaging or enhanced photosensitivity in two-photon sensitization, respectively.

M. Albota, S. E. Hess, W. W. Webb, C. Xu, School of Applied Physics and Engineering, and Developmental Resource for Biophysical Imaging Opto-Electronics, Cornell University, Ithaca, NY 14853, USA. D. Beljonne, J.-L. Brédas, T. Kogej, Center for Research on Molecular Electronics and Photonics, Université de Mons-Hainaut, Place du Parc 20, B-7000 Mons, Belgium. J. E. Ehrlich, Jet Propulsion Laboratory, 67-119, California Institute of Technology, Pasadena, CA 91109, USA. J.-Y. Fu, A. A. Heikal, M. Rumi, X.-L. Wu, Molecular Materials Resource Center, Beckman Institute, 139-74, California Institute of Technology, Pasadena, CA 91125, USA, and Jet Propulsion Laboratory, 67-119, California Institute of Technology, Pasadena, CA 91109, USA. M. D. Levin, D. McCord-Maughon, H. Röckel, Molecular Materials Resource Center, Beckman Institute, 139-74, California Institute of Technology, Pasadena, CA 91125, USA. S. R. Marder and J. W. Perry, Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA, Molecular Materials Resource Center, Beckman Institute, 139-74, California Institute of Technology, Pasadena, CA 91125, USA, and Jet Propulsion Laboratory, 67-119, California Institute of Technology, Pasadena, CA 91109, USA. G. Subramaniam, Department of Chemistry, Pennsylvania State University, Hazleton, PA 18201, USA.
*   To whom correspondence should be addressed.

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