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3.3. AZOBENZENE CONTAINING SOLID FILMS
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Figure 3.4. Swelling behavior of slide-ring gels in DMSO upon alternate irradiation of UV and visible light. D and D0 are diameters of the gel and inner diameter of mold capillary, respectively. Source: Sakai et al., 2007.
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The use of structural changes of photoisomerizable chromophores to change the size of polymers was rst proposed by Merian (1966). He observed that a nylon lament fabric dyed with an azobenzene derivative shrank upon photoirradiation. This effect is ascribed to the photochemical structural change of the azobenzene moiety absorbed on the nylon bers. However, the observed shrinkage was very small (only B0.1%), and subsequent to this work, much effort was made to nd new photomechanical systems with an enhanced ef ciency (Irie, 1990; Smets and De Blauwe, 1974). Eisenbach (1980) investigated the photomechanical effect of poly(ethyl acrylate) networks (3) cross-linked with azobenzene moieties and observed that the polymer network contracted upon exposure to UV light (caused by the trans cis isomerization of the azobenzene cross-links) and expanded upon irradiation of visible light (caused by cis trans back-isomerization; Fig. 3.5). This photomechanical effect is mainly due to the conformational change of the azobenzene crosslinks by the trans cis isomerization of the azobenzene chromophore. However, the degree of deformation was small (0.2%).
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CHAPTER 3: PHOTODEFORMABLE MATERIALS AND PHOTOMECHANICAL EFFECTS
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Figure 3.5. Schematic representation of photomechanical effect in a poly(ethyl acrylate) network with azobenzene cross-links upon irradiation. f = Force. Source: Eisenbach, 1980.
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Matejka et al. synthesized several types of photochromic polymers based on a copolymer of maleic anhydride and styrene with azobenzene moieties both in the side chains and cross-links of the polymer network (Matejka et al., 1981; Matejka and Dusek, 1981; Matejka et al., 1979) . The photomechanical effect was enhanced by an increase in the content of photochromic groups, and the photoinduced contraction of the sample amounted to 1% for a polymer with 5.4 mol% azobenzene moieties. The photoinduced expansion of thin lms of polymers (4) containing azobenzene chromophores was explored in real time by single wavelength ellipsometry (Fig. 3.6; Tanchak and Barret, 2005). The initial expansion of the azobenzene polymer lms of thickness ranging from 25 to 140 nm was irreversible and amounted to 1.5% 4%. Subsequently, reversible expansion was observed with repeated irradiation cycles; the relative expansion was 0.6% 1.6%. Recent development of single-molecular force spectroscopy by atomic force microscopy (AFM) techniques has enabled quite successfully the measurement of mechanical force produced at a molecular level. Gaub and coworkers reported on a phototriggered polymer, which contains azobenzene units as part of the main polymer backbone (5; Adoc=1-adamantyloxycarbonyl) (Holland et al., 2003; Hugel et al., 2002). This key study demonstrates a photomechanical cycle using
3.3. AZOBENZENE CONTAINING SOLID FILMS
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Figure 3.6. Schematic representation of photoexpansion effect in the thin lms. Source: Tanchak and Barret, 2005.
a single azobenzene polymer molecule (Fig. 3.7), representing the rst experimental work using photomechanical energy conversion in a single-molecule device, in which a polymer is covalently coupled to an AFM tip and a glass slide. The azobenzene units are reversibly switched at two distinctly different wavelengths between an extended trans and a contracted cis con guration. Applying focused UV light (l=420 nm) to the glass substrate having the polymer bound to it results in stretching of the polymer since its conformation is switched to the alltrans state. Subsequent irradiation with light of lmax=356 nm causes relaxation of the polymer and conversion to the all-cis conformation. The material can be repeatedly cycled between these two states, even when an external load is put on the AFM tip. The mechanical work performed by the azobenzene polymer strand by trans cis photoisomerization was approximately 4.5 10 20 J. This mechanical work at the molecular level results from a macroscopic photoexcitation, and the real quantum ef ciency of the photomechanical work for the given cycle in their AFM setup was only on the order of 10 18. However, a maximum ef ciency of the photomechanical energy conversion at a molecular level can be estimated as 0.1, if it is assumed that each switching of a single azobenzene unit is initiated by a single photon with an energy of 5.5 10 19 J (l=365 nm) (Holland et al., 2003; Hugel et al., 2002).