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

Science  11 Sep 1998:
Vol. 281, Issue 5383, pp. 1653-1656
DOI: 10.1126/science.281.5383.1653

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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.

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