Novel pendant azobenzene/polymer systems for second harmonic generation and optical data storage

Abstract New poly(methyl methacrylate)s bearing push–pull azo-moieties, with the azo-dye content ranging from 31 wt% to 100 wt%, are synthesized by (co)polymerization of a methacrylamide-based azo-monomer. The high reactivity of the colored monomer allowed well-balanced structures to be achieved, characterized by a suitable thermal stability. The second harmonic generation efficiency of the poled samples is investigated by means of the SHG Maker fringes setup. Features that hinder the translation of the azo-moiety optical nonlinearity in the material at the macroscopic level are debated. The results underline the role of chromophore–chromophore and chromophore–polymer interactions on the alignment of the azo-moieties. The polarity of the polymer matrix is proven to influence the chromophore–chromophore interactions. Two-photon absorption is employed for gray scale encoding of second harmonic signals on poled thin films, thus pointing out the possibility to employ these new materials for optical data storage applications.

[1]  Zouheir Sekkat,et al.  Photoreactive organic thin films , 2002 .

[2]  Kenneth D. Singer,et al.  Second harmonic generation in poled polymer films , 1986 .

[3]  C. Hagiopol.  Copolymerization: Toward a Systematic Approach , 1999 .

[4]  L. Michael Hayden,et al.  Maker fringes revisited: second-harmonic generation from birefringent or absorbing materials , 1995 .

[5]  Akira Yamashita,et al.  Molecular Weight Distribution and Correlation between Chemical Composition and Molecular Weight in a High-Conversion Copolymer of Styrene-Methyl Acrylate , 1978 .

[6]  Francois Kajzar,et al.  Polymeric Materials and their Orientation Techniques for Second-Order Nonlinear Optics , 2003 .

[7]  A. Eceiza,et al.  Enhanced stability of photo-induced anisotropy due to intermolecular interactions in an azo-prepolymer confined in block copolymer , 2013 .

[8]  P. Rochon,et al.  Photoinduced birefringence in copolymers containing Disperse Red 1 and styrene , 2000 .

[9]  Alain Fort,et al.  Rewritable optical data storage in azobenzene copolymers. , 2006, Optics express.

[10]  Alexis Goulet-Hanssens,et al.  Photo‐control of biological systems with azobenzene polymers , 2013 .

[11]  J. Michl,et al.  Crystalline arrays of pairs of molecular rotors: correlated motion, rotational barriers, and space-inversion symmetry breaking due to conformational mutations. , 2013, Journal of the American Chemical Society.

[12]  F. Nicolescu,et al.  Synthesis and characterization of side-chain poly(methacrylate)s bearing new azo-moieties , 2010 .

[13]  Alain Fort,et al.  Image storage through gray-scale encoding of second harmonic signals in azo-dye copolymers , 2007 .

[14]  B H Robinson,et al.  The role of London forces in defining noncentrosymmetric order of high dipole moment-high hyperpolarizability chromophores in electrically poled polymeric thin films. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[15]  Tomiki Ikeda,et al.  Photo-mechanical effects in azobenzene-containing soft materials. , 2007, Soft matter.

[16]  A. Sugita,et al.  Second-order nonlinear optical susceptibilities of nonelectrically poled DR1-PMMA guest-host polymers. , 2013, The journal of physical chemistry. B.

[17]  Xiaogong Wang,et al.  Photoresponsive behavior of two well-defined azo polymers with different electron-withdrawing groups on push–pull azo chromophores , 2013 .

[18]  Donald G. Truhlar,et al.  Improving the Accuracy of Hybrid Meta-GGA Density Functionals by Range Separation , 2011 .

[19]  E. G. McRae.  Theory of Solvent Effects on Molecular Electronic Spectra. Frequency Shifts , 1957 .

[20]  P. Batail,et al.  Effect of the counter cation on the third order nonlinearity in anionic Au dithiolene complexes , 2012 .

[21]  C. Bosshard,et al.  Organic Nonlinear Optical Materials , 2001, CLEO/Europe Conference on Lasers and Electro-Optics.

[22]  Seth R Marder,et al.  Organic nonlinear optical materials: where we have been and where we are going. , 2006, Chemical communications.

[23]  Naoto Tsutsumi,et al.  Stable polymeric materials for nonlinear optics: a review based on azobenzene systems , 2004 .

[24]  M. Sallé,et al.  Reversible two-photon optical data storage in coumarin-based copolymers. , 2010, Journal of the American Chemical Society.

[25]  T. Kwei.  The effect of hydrogen bonding on the glass transition temperatures of polymer mixtures , 1984 .

[26]  S. Burdette,et al.  Photoisomerization in different classes of azobenzene. , 2012, Chemical Society reviews.

[27]  Mitica Cezar Spiridon,et al.  2-Oxazoline based photo-responsive azo-polymers. Synthesis, characterization and isomerization kinetics , 2013 .

[28]  X. Duan,et al.  Preparation, photoisomerization, and microfabrication with two‐photon polymerization of crosslinked azo‐polymers , 2013 .

[29]  Satoshi Kawata,et al.  Three-Dimensional Optical Data Storage Using Photochromic Materials. , 2000, Chemical reviews.

[30]  Paul Rochon,et al.  Azo Polymers for Reversible Optical Storage. 5. Orientation and Dipolar Interactions of Azobenzene Side Groups in Copolymers and Blends Containing Methyl Methacrylate Structural Units , 1995 .

[31]  Hai-Yun Li,et al.  Synthesis of a main-chain liquid crystalline azo-polymer via “click” chemistry , 2013, Colloid and Polymer Science.

[32]  S. Couris,et al.  Third-order nonlinear optical response of push–pull azobenzene polymers , 2012 .

[33]  L. Săcărescu,et al.  Study of the nanostructuration capacity of some azopolymers with rigid or flexible chains , 2013 .

[34]  Rainer Hagen,et al.  Photoaddressable Polymers for Optical Data Storage , 2001 .

[35]  Philippe Pretre,et al.  Second‐order polarizabilities of nitropyridine derivatives determined with electric‐field‐induced second‐harmonic generation and a solvatochromic method: A comparative study , 1992 .

[36]  Stephen T. Kowel,et al.  Second-harmonic generation and absorption studies of polymer-dye films oriented by corona-onset poling at elevated temperatures , 1989 .

[37]  Y. Morille,et al.  Image storage in coumarin-based copolymer thin films by photoinduced dimerization. , 2013, Optics letters.

[38]  John T. Sheridan,et al.  A Review of the Optimisation of Photopolymer Materials for Holographic Data Storage , 2012 .

[39]  Mark S. Gordon,et al.  General atomic and molecular electronic structure system , 1993, J. Comput. Chem..

[40]  J. Grote,et al.  Grating inscription in picosecond regime in thin films of functionalized DNA. , 2007, Optics express.

[41]  Jing Ma,et al.  Tuning the absorption spectra and nonlinear optical properties of D-π-A azobenzene derivatives by changing the dipole moment and conjugation length: a theoretical study , 2011 .

[42]  M. Sallé,et al.  Nonlinear absorption reversing between an electroactive ligand and its metal complexes. , 2012, Optics express.

[43]  A. Immirzi,et al.  Prediction of density in organic crystals , 1977 .

[44]  O. Krupka,et al.  Second- and third-order nonlinearities of novel push-pull azobenzene polymers. , 2011, The journal of physical chemistry. B.

[45]  Tomiki Ikeda,et al.  Smart light-responsive materials : azobenzene-containing polymers and liquid crystals , 2009 .