DOI: 10.1126/science.281.5383.1653. Design of Organic Molecules with Large Two-Photon Absorption Cross Sections

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

10.1126/science.281.5383.1653

Crossref journal-article

American Association for the Advancement of Science (AAAS)

Science (221)

Abstract

A strategy for the design of molecules with large two-photon absorption cross sections, δ, 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 δ. Synthesized bis(styryl)benzene derivatives with donor-π-donor, donor-acceptor-donor, and acceptor-donor-acceptor structural motifs exhibit exceptionally large values of δ, 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 δ values in good agreement with experimental values. The combination of large δ 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.

Bibliography

Albota, M., Beljonne, D., BreÌdas, J.-L., Ehrlich, J. E., Fu, J.-Y., Heikal, A. A., Hess, S. E., Kogej, T., Levin, M. D., Marder, S. R., McCord-Maughon, D., Perry, J. W., RoÌckel, H., Rumi, M., Subramaniam, G., Webb, W. W., Wu, X.-L., & Xu, C. (1998). Design of Organic Molecules with Large Two-Photon Absorption Cross Sections. Science, 281(5383), 1653â1656.

Authors 18

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

References 25 Referenced 2,049

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The two-photon absorption cross sections were determined by two-photon–excited fluorescence measurements with 5-ns 10-Hz pulses from a Nd:yttrium-aluminum-garnet–pumped optical parametric oscillator-amplifier system. The setup consisted of two arms to allow relative measurements with respect to bis-1 4-(2-methylstyryl)benzene (in cyclohexane) fluorescein (in pH 11 water) and rhodamine B (in methanol). The sample chromophores were dissolved in toluene (10 −4 M concentration); an approximately collimated beam was used to excite the samples over the 1-cm length of the cuvettes. The fluorescence emitted at right angles to the excitation was collected and focused onto photomultiplier tube detectors. The intensity of the incident beam was adjusted to assure excitation in the intensity-squared regime.
Kennedy S. M., Lytle F. E., Anal. Chem. 58, 2643 (1986); (10.1021/ac00126a014) / Anal. Chem. by Kennedy S. M. (1986)
. We scaled the peak δ value reported in this paper by a factor chosen to match the long-wavelength data reported therein with that of (7).
M. Lipson M. Levin S. R. Marder J. W. Perry unpublished results.
B. H. Cumpston et al. in preparation.
Support from the NSF (Chemistry Division) Office of Naval Research and the Air Force Office of Scientific Research (AFOSR) and its Defense University Research Instrumentation Program at the California Institute of Technology is gratefully acknowledged. The research described in this paper was performed in part by the Jet Propulsion Laboratory California Institute of Technology as part of its Center for Space Microelectronics Technology and was supported by the Ballistic Missile Defense Organization Innovative Science and Technology Office and AFOSR through an agreement with NASA. The work in Mons was carried out within the framework of the Belgium Prime Minister Office of Science Policy “Pôle d'Attraction Interuniversitaire en Chimie Supramoléculaire et Catalyse” PAI 4/11 and is partly supported by the Belgium National Fund for Scientific Research (FNRS-FRFC) and an IBM-Belgium Academic Joint Study; D.B. is a Chercheur Qualifié FNRS and T.K. is a Ph.D. grant holder of Fund for Research in Industry and Agriculture. The femtosecond two-photon fluorescence excitation cross-section measurements were carried out in the Developmental Resource for Biophysical Imaging Opto-electronics at Cornell University with support of NIH–National Center of Research Resources and NSF. G.S. acknowledges support from the NASA-JOVE program.

Dates

Type	When
Created	23 years, 1 month ago (July 27, 2002, 5:43 a.m.)
Deposited	1 year, 7 months ago (Jan. 12, 2024, 10:24 p.m.)
Indexed	1 day ago (Sept. 3, 2025, 6:20 a.m.)
Issued	26 years, 11 months ago (Sept. 11, 1998)
Published	26 years, 11 months ago (Sept. 11, 1998)
Published Print	26 years, 11 months ago (Sept. 11, 1998)

Funders 0

None

BibTeX

@article{Albota_1998, title={Design of Organic Molecules with Large Two-Photon Absorption Cross Sections}, volume={281}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.281.5383.1653}, DOI={10.1126/science.281.5383.1653}, number={5383}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Albota, Marius and Beljonne, David and Brédas, Jean-Luc and Ehrlich, Jeffrey E. and Fu, Jia-Ying and Heikal, Ahmed A. and Hess, Samuel E. and Kogej, Thierry and Levin, Michael D. and Marder, Seth R. and McCord-Maughon, Dianne and Perry, Joseph W. and Röckel, Harald and Rumi, Mariacristina and Subramaniam, Girija and Webb, Watt W. and Wu, Xiang-Li and Xu, Chris}, year={1998}, month=sep, pages={1653–1656} }

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      "unstructured": "B. H. Cumpston et al. in preparation."
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      "unstructured": "Support from the NSF (Chemistry Division) Office of Naval Research and the Air Force Office of Scientific Research (AFOSR) and its Defense University Research Instrumentation Program at the California Institute of Technology is gratefully acknowledged. The research described in this paper was performed in part by the Jet Propulsion Laboratory California Institute of Technology as part of its Center for Space Microelectronics Technology and was supported by the Ballistic Missile Defense Organization Innovative Science and Technology Office and AFOSR through an agreement with NASA. The work in Mons was carried out within the framework of the Belgium Prime Minister Office of Science Policy \u201cP\u00f4le d'Attraction Interuniversitaire en Chimie Supramol\u00e9culaire et Catalyse\u201d PAI 4/11 and is partly supported by the Belgium National Fund for Scientific Research (FNRS-FRFC) and an IBM-Belgium Academic Joint Study; D.B. is a Chercheur Qualifi\u00e9 FNRS and T.K. is a Ph.D. grant holder of Fund for Research in Industry and Agriculture. The femtosecond two-photon fluorescence excitation cross-section measurements were carried out in the Developmental Resource for Biophysical Imaging Opto-electronics at Cornell University with support of NIH\u2013National Center of Research Resources and NSF. G.S. acknowledges support from the NASA-JOVE program."
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