Arylmethylene-1,3-indandione based molecular glasses: Third order optical non-linearity

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Journal Article
Dyes and Pigments, 2012, 95 (1), pp. 33 - 40
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The synthesis and new optical features of three indan-1,3-dione class structures is reported. The simple arylmethylene-1,3-indandione structure 2-(4-diethylaminobenzylidene)indan-1,3-dione was used to design two linked structures: 1,3-bis-{3-hydroxy-4-[4-diethylamino-1-(1,3-dioxoindan-2- ylmethylene)benzen-3-yloxy]-1-thiabuthyl}benzene and 4,4′-bis-{{3-hydroxy- 4-[4-diethylamino-1-(1,3-dioxoindan-2-ylmethylene)benzen-3-yloxy]-1-thiabutyl} phenyl}sulfide. In contrast to the simple compound, which readily crystallized, the linked derivatives remained in an amorphous phase and are considered as molecular glasses with respective glass transition temperatures 88 and 100°C. For non-linear optical investigations samples were prepared as a guest-host system in polycarbonate matrix (10%). The Maker-fringe technique was used to investigate the third harmonic generation at a wavelength of 355 nm (YAG laser). Third-order non-linear susceptibility χ(3)values were extracted 5.75·10-21m2V-2, 8.60·10-21m2V-2, 16.85·10-21m2V-2for these respective indandiones while modeling the experimental results. To evaluate the susceptibility of the indan-1,3-dione derivatives third harmonic generation a comparative experiment for a reference azodye in polycarbonate was performed. The results show an important feature - higher molecular second order hyperpolarizability for the linked structures. NMR, MS, IR, UV-VIS, XRD and elemental analysis were used to structurally characterize the new compounds and ellipsometry was applied to interpret the non-linear optical results. © 2012 Elsevier Ltd. All rights reserved.
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