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Perhaps of a range as wide as the interesting phenomena displayed by azo aromatic compounds is the variety of molecular systems into which these chromophores can be incorporated. In addition to LC media and amorphous glasses, azobenzenes can be incorporated into self-assembled monolayers and superlattices, sol gel silica glasses, and various biomaterials. The photochromic or photoswitchable nature of azobenzenes can also be used to control the properties of novel small molecules, using an attached aromatic azo group. A review will be presented here of the photochemical and photophysical nature of chromophores in host polymers, the geometric and orientational consequences of this isomerization, and some of the interesting ways in which these phenomena have been expolited recently to exert control over solution and biochemical properties using light. This photoisomerization can be exploited as a photoswitch to orient the chromophore (which induces birefringence), or even to perform all-optical surface topography patterning. These photomotions enable many interesting applications, ranging from optical components and lithography to sensors and smart materials.
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1.1.1. Azobenzene Chromophores
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In this text, as in most on the subject, we use azobenzene and azo in a general way: to refer to the class of compounds that exhibit the core azobenzene structure, with different ring substitution patterns (even though, strictly, these compounds should be referred to as diazenes ). There are many properties common to nearly all azobenzene molecules. The most obvious is the strong electronic absorption of the conjugated p system. The absorption spectrum can be tailored, via the ring substitution pattern, to lie anywhere from the UV to the visible red region. It is not surprising that azobenzenes were originally used as dyes and colorants, and up to 70% of the world s commercial dyes are still azobenzene-based (Zollinger, 1987, 1961). The geometrically rigid structure and large aspect ratio of azobenzene molecules make them ideal mesogens: azobenzene small molecules and polymers functionalized with azobenzene can exhibit LC phases (Mohlmann and van der Vorst, 1989; Kwolek et al., 1985). The most startling and intriguing characteristic of the azobenzenes is their highly ef cient and fully reversible photoisomerization. Azobenzenes have two stable isomeric states, a thermally stable trans con guration and a metastable cis form. Remarkably, the azo chromophore can interconvert between these isomers upon absorption of a photon. For most azobenzenes, the molecule can be optically isomerized from trans to cis with light anywhere within the broad absorption band, and the molecule will subsequently thermally relax back to the trans state on a timescale dictated by the substitution pattern. This clean photochemistry is central to azobenzene s potential use as a tool for nanopatterning. Azobenzenes can be separated into three spectroscopic classes, well described by Rau (1990): azobenzene-type molecules, aminoazobenzene-type molecules, and pseudo-stilbenes (refer to Fig. 1.1 for examples). The particulars of their absorption spectra (shown in Fig. 1.2) give rise to their prominent colors: yellow, orange, and red, respectively. Many azos exhibit absorption characteristics similar to the unsubstituted azobenzene archetype. These molecules exhibit
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Figure 1.1. Examples of azomolecules classi ed as (a) azobenzenes, (b) aminoazobenzenes, and (c) pseudo-stilbenes.
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a low intensity n-p* band in the visible region and a much stronger p-p* band in the UV. Although the n-p* is symmetry-forbidden for trans-azobenzene (C2h), vibrational coupling and some extent of nonplanarity nevertheless make it observable (Rau, 1968).
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Figure 1.2. Schematic of typical absorbance spectra for trans-azobenzenes. The azobenzene-type molecules (solid line) have a strong absorption in the UV, and a low intensity band in the visible (barely visible in the graph). The aminoazobenzenes (dotted line) and pseudo-stilbenes (dashed line) typically have strong overlapped absorptions in the visible region.
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