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Under illumination with polarized light, azobenzene moieties undergo angleselective E Z photoisomerization cycles depending on the angle between the transition dipole moment of the azobenzene unit and the electric eld vector of the exiting light. The linear polarized irradiation tends to orient the chromophores perpendicular to the electric eld vector of the exiting light, generating an oblate orientation distribution. This photoorientation process takes place via a number of angular-dependent photoselection events in the steady state of the photoisomerization, and it is connected with the rotational diffusion of the chromophores. This effect occurs in all media. However, stability of the induced anisotropy depends on the matrix properties. In some materials (e.g, glassy polymers), this effect may be cooperative, which means causing an orientation of nonphotochromic side groups and other polymer segments toward the same direction and often to a comparable degree of anisotropy (Shibaev et al., 1996; McArdle, 1992). The photoinduced order is stable in the glassy state of the matrix, and the anisotropy disappears above the glass transition temperature. Considerable research efforts are currently focused on the interplay between molecular architecture, intermolecular interactions, order, and macroscopic properties (Lehn, 1995; Ikkala and ten Brinke, 2002; Moore, 1966). The construction of materials with different functionalities, easy processing, high
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anisotropy and stability through self-assembly, and self-organization processes, in which molecules associate spontaneously into ordered aggregates as a result of noncovalent interactions or entropic factors, is becoming one of the primary frontiers of materials research. To achieve this goal, several strategies such as H-bonding (Macdonald and Whitesides, 1994), metal coordination (Lehn, 1990), charge-assisted H-bonding (Hosseini, 2003), and, more recently, ISA (Faul and Antonetti, 2003) have been investigated. A rather large number of these activities are directed to generate mesophases, where the mesogenic units are formed by intermolecular interactions. The mutual order is encoded not only in the shape and chemical functionality of the objects involved but also in the strength and directionality of the secondary interactions used. In classical supramolecular chemistry, these interactions are usually hydrogen bridges or coordinative metal binding. However, molecular recognition and amphiphilic association should also be considered. Table 2.1 summarizes the most important interactions playing the main role in organization of organic supramolecular materials. Manipulation of structural and macroscopic order in lms and bulk solids, however, remains a major challenge for all of these approaches. The approach of deriving new photosensitive materials using secondary noncovalent interactions like H-bonding and ionic interactions between different units such as polymers and low-molecular-weight functionalized units has gained a great interest in the past decade. This approach allows the development of a new generation of smart materials and their application in optoelectronics, holography, data recording, and imaging systems. New materials may advantageously combine the properties of polymers ( lm forming) and low-molecular-weight components (photochromism, high optical activity, easy processing, etc.). The simplest way to use secondary interactions in design of photosensitive material would be to introduce them between the polymer backbone and functional photosensitive groups. This approach would allow direct comparison of photoorientation properties with already well-studied materials. A general application of this idea between different high-molecular-weight and
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TA B L E 2 . 1 . Interactions and Some of Their Properties
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Interaction van der Waals H bonding Coordination binding Fit interactions Amphiphilic Ionic Covalent
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Strength (kJ/mol) B50 5 65 50 200 10 100 5 50 50 250a 350
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Range Short Short Short Short Short Long Short
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Character Nonselective, nondirectional Selective, directional directional Very selective Nonselective Nonselective irreversible
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Data are for organic media, dependent on solvent and ion solution.
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Source: Faul and Antonetti 2003. Reproduced with permission from Wiley VCH.
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CHAPTER 2: SUPRAMOLECULAR AZOBENZENE MATERIALS
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Figure 2.3. Principles of molecular construction of LC polymers by self-assembly induced by hydrogen or ionic bonding.
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low-molecular-weight tectonic unit is shown in Fig. 2.3. For the rst time, this approach was realized for photosensitive polymer azobenzene unit complexes using ionic interaction (Fig. 2.2d) (Meyer et al., 1991) and H-bonding (Fig. 2.4a) (Kato et al., 1996), where nonlinear optical properties and in uence of UV-vis irradiation on a reversible isothermal nematic isotropic phase transition have been investigated, respectively. The development of H-bonded complexes is now considered. An in uence of UV irradiation on optical properties of low-molecular-weight azobenzene-containing material (Fig. 2.4b) has been investigated (Aoki et al., 2000) on the basis of such interactions. The rst observation of photoinduced optical anisotropy in Hbonded complexes of azobenzene dyes and copolymers (Fig. 2.4b) has been recently demonstrated (Medvedev et al., 2005). In this case, the induced anisotropy was stable, and the maximum dichroic ratio of 2 has been observed. A kinetics of the induction of birefringence (maximum value of ca. 0.01) in one of these complexes is shown in Fig. 2.5. An in uence of H-bonding on the mesomorphic and photoorientation properties was recently demonstrated (Cui and Zhao, 2004). In this approach, the amorphous azopyridine side-chain polymer was converted into liquid crystalline polymers through self-assembly with a series of commercially available, aliphatic, and aromatic carboxylic acids (Fig. 2.4d).
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