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

Albota, Marius and Beljonne, David and Breédas, 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 Roöckel, Harald and Rumi, Mariacristina and Subramaniam, Girija and Webb, Watt W. and Wu, Xiang-Li and Xu, Chris (1998) Design of Organic Molecules with Large Two-Photon Absorption Cross Sections. Science, 281 (5383). pp. 1653-1656. ISSN 0036-8075. doi:10.1126/science.281.5383.1653.

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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.

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Additional Information:© 1998 American Association for the Advancement of Science. Received 7 May 1998; accepted 31 July 1998. 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 Qualifé 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.
Funding AgencyGrant Number
Office of Naval Research (ONR)UNSPECIFIED
Air Force Office of Scientific Research (AFOSR)UNSPECIFIED
Ballistic Missile Defense OrganizationUNSPECIFIED
Belgium Office of Science Policy (BELSPO)PAI 4/11
Fonds de la Recherche Scientifique (FNRS)UNSPECIFIED
IBM-Belgium Academic Joint StudyUNSPECIFIED
Fonds pour la Formation à la Recherche dans l’índustrie et dans l’Ágriculture (FRIA-Belgium)UNSPECIFIED
Issue or Number:5383
Record Number:CaltechAUTHORS:20141202-130555933
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Official Citation: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, and Chris Xu Science 11 September 1998: 281 (5383), 1653-1656. [DOI:10.1126/science.281.5383.1653]
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:52277
Deposited By: Tony Diaz
Deposited On:02 Dec 2014 21:24
Last Modified:10 Nov 2021 19:23

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