Synthesis, structure and properties of a new two-photon photopolymerization initiator

A new two-photon free-radical photopolymerization initiator, (E,E)-4-{2-[p′-(N,N-di-n-butylamino)stilben-p-yl]vinyl}pyridine (abbreviated to DBASVP), has been synthesized. Quantum chemistry calculations showed that the new initiator possesses a large delocalized π electron system, a large change in dipole moment on transition to the excited state and a large transition moment. The calculated two-photon absorption cross-section is as high as 881.34 × 10−50 cm4 s photon−1. The single-photon and two-photon absorption and fluorescence properties in various solvents have been investigated carefully. The new initiator exhibits outstanding solvent-sensitivity, which experimentally interprets the excellent electron delocalized properties of the molecule. A microstructure has been fabricated under irradiation at 800 nm using a 200 fs, 76 MHz Ti:sapphire femtosecond laser.

[1]  A. Klamt Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena , 1995 .

[2]  J. Young,et al.  Genome sequencing: The ABC of symbiosis , 2001, Nature.

[3]  Peter Fromherz,et al.  Monopole-Dipole Model for Symmetrical Solvatochromism of Hemicyanine Dyes , 1995 .

[4]  Yi Luo,et al.  Effects of π centers and symmetry on two-photon absorption cross sections of organic chromophores , 2001 .

[5]  U. Narang,et al.  Characterization of a New Solvent-Sensitive Two-Photon-Induced Fluorescent (Aminostyryl)pyridinium Salt Dye , 1996 .

[6]  J. Demas,et al.  Measurement of photoluminescence quantum yields. Review , 1971 .

[7]  Paras N. Prasad,et al.  Studies of two-photon pumped frequency-upconverted lasing properties of a new dye material , 1997 .

[8]  Seth R. Marder,et al.  Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication , 1999, Nature.

[9]  J. Simon,et al.  Intramolecular electron transfer and solvation , 1987 .

[10]  Saulius Juodkazis,et al.  Microcavities in polymeric photonic crystals , 2001 .

[11]  Paras N. Prasad,et al.  Three-dimensional optical circuitry using two-photon-assisted polymerization , 1999 .

[12]  Pál Ormos,et al.  Complex micromachines produced and driven by light , 2001, CLEO 2002.

[13]  W. Rettig,et al.  Photoinduced Intramolecular Charge Transfer in a Series of Differently Twisted Donor−Acceptor Biphenyls As Revealed by Fluorescence , 1999 .

[14]  Paras N. Prasad,et al.  Highly Active Two-Photon Dyes: Design, Synthesis, and Characterization toward Application , 1998 .

[15]  Toomas Tamm,et al.  UV-visible spectra of some nitro-substituted porphyrins , 1995 .

[16]  W. Webb,et al.  Design of organic molecules with large two-photon absorption cross sections. , 1998, Science.