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Probably, there is no other molecule as azobenzene that has been so well known for a long time and, nevertheless, still brings off surprising phenomena. Though azobenzene once started off as a simple dye a molecule just absorbing light it has been recognized as photochrome, a molecule changed by light and has since become indispensable in optics as a molecule controlling light. Recently, it has revealed a completely different characteristic a molecule moved by light. The combination of all these properties in one molecule makes it favored for a wide range of optical applications. The application of azobenzenes is further supported by the availability of various commercial dyes or by simplicity of their synthesis. Different material aspects and optical applications of azobenzene may be found in some recent reviews (Seki, 2007; Shibaev et al., 2003, 1996; Natansohn and Rochon, 2002; Yager and Barrett, 2001; Viswanathan et al., 1999; Fuhrmann and Wendorff, 1997; Ichimura, 1996; Ichimura et al., 1994). Most azobenzene derivatives can be isomerized reversibly between the E and Z isomeric forms by light or heat. Some derivatives may show phototautomerism, photodimerization, photoreduction, and fading. The effects discussed in this chapter are based on E Z photoisomerization of aromatic azobenzenes (Rau, 1990) also known in the literature as trans cis photoisomerization. Photoisomerization reaction of azobenzene allows the reversible change of molecular properties such as absorbance, dipole moment, polarity, geometric shape, and others. These molecular changes may be used to control macroscopic properties of materials. For example, the change of the geometric form of
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Smart Light Responsive Materials. Edited by Yue Zhao and Tomiki Ikeda Copyright r 2009 John Wiley & Sons, Inc.
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molecules can affect the formation of molecular aggregates (Stumpe et al., 1996; Shimomura, 1993), induce phase transitions in the material (Hasegawa et al., 1999), or change the enzyme activity (Willner et al., 1991). Recently, the photoinduced change of the geometric shape of macroscopic objects has been demonstrated (Ikeda et al., 2007; Bublitz et al., 2000; Seki et al., 1996). If the irradiating light activates both E Z and back Z E transitions, the steady state of photoreaction is established, whereas the molecules undergo repeated isomerization cycles. In many cases, it is not an equilibrium concentration of both isomeric forms that is important, it is the light-induced dynamics, that is, the continuing movement of the chromophore. In other words, the isomerizing azobenzene molecule works as a light-driven molecular motor, whose power and force direction may be controlled by the parameters of the irradiating light, such as wavelength, polarization, or intensity distribution. This statement is kept in mind when discussing the photoinduced processes in this chapter. The irradiation with polarized light results in the preferential orientation of azobenzene molecules perpendicularly to the light electric eld vector orientational order is induced, the system becomes anisotropic. The photoinduction of molecular order causes plenty of macroscopic effects, including optical anisotropy, which is one of the subjects in this chapter. After the actinic light is switched off, the photoproduct reacts back to the thermally stable E isomeric form and the initial state is restored at the molecular level. It may be changed thermally or by irradiation with actinic light. The uniformity of the photoreaction and rebuilding of the initial state at the molecular level guarantee the complete reversibility of the processes. Note that an important advantage of azobenzenes is that both photoisomerization processes take place with high quantum yields and without further side reactions. Therefore, in contrast to most other chromophores, a number of isomerization cycles can be carried out without material destruction. All these effects have been widely addressed in the literature. Since the pioneer work on photoinduction of optical anisotropy in photosensitive organic materials (Weigert, 1929), the dynamic photoorientation in azobenzene-containing viscous solutions (Makushenko et al., 1971) and dye-polymer blends (Gibbson et al., 1991; Todorov et al., 1984), and the stable anisotropy in functionalized glassy polymers (Eich et al., 1987) have been studied. Typical optical applications of the photoinduced order include polarization elements (Petrova et al., 2003), diffraction optical elements (Martinez-Ponce et al., 2004), waveguides (Karimi-Alavijeh et al., 2008; Luo et al., 2007), optical storage (Nedelchev et al., 2003; Hagen and Bieringer, 2001; Sabi et al., 2001), all-optical switching (Luo et al., 2005), multiplexing (Ilieva et al., 2005), alignment of liquid crystals (Ichimura, 1996; Ichimura et al., 1994) and bulk alignment of liquid crystalline polymers (Zen et al., 2002; Rosenhauer et al., 2001; Han et al., 2000; Fischer et al., 1997; Stumpe et al., 1991), and orientation of further functional groups in liquid crystalline (LC) polymers (Rosenhauer et al., 2005). Repeated E Z isomerization may also result in a translation motion of the molecules. This motion becomes manifested on spatially inhomogeneous irradiation. The phenomenon has been known as a light-driven mass transport or, with
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