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NIPA
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[Irie, 1993]
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HEAM [Menzel, 1995]
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atrans aUV-atrans
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a in 1C per mol% azo in the polymer. NIPA poly(N-isopropylacrylamide), HEAM hydroxyethylacrylamide, HPMC hydroxypropyl methylcellulose. N.A. not available.
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a more polar azobenzene with 4umethoxyethyloxy substituent. not shown in the ref, our estimate uses LCST of c.a. 551C for the unmodi ed chain.
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7.2. FROM CLOUD POINT TO ASSOCIATIVE PHASE SEPARATION
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The basic origins of photovariation of LCST are the photomodulation of hydrophobic binding and Van der Waals interactions. To enhance the effect (at xed degree of modi cation with azo, i.e., to achieving larger a values) it is possible to optimize the effect of isomerization on the chromophore chromophore (attractive) interaction and the chromophore-water (repulsive) interaction. The energy of hydrophobic association is certainly dif cult to estimate, but should depend mainly on the number of carbon atoms that can be transferred in apolar microdomains. If the azos are fully accessible in the modi ed polymers (e.g., exible chains, long spacers), the isomerization does not markedly affect the hydrophobic binding. In contrast, the E Z conversion modi es the dipole interactions to an extent that should vary in proportion to the dipole moments of E and Z forms (irrespective of polymer composition), making thus the aUV atrans coef cient in Equation 7.1 proportional to the dipole variation. We remark that almost optimal photoswitches of dipolar interaction have been reached in the published investigations, because the azobenzenes used were essentially apolar under their trans form and polar under their cis form. Improvements are therefore not obvious, and shall be devised on new basis, for instance, using additional enthalpic contributions to the intrachain interaction.
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7.2.2. Complexation and Solubility of Chains
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Typical attempts at enhancing the impact of E Z conversion on intrachain and monomer-solvent interactions use solution of CDs in water. CDs form host guest inclusion complexes with azobenzene derivatives (Zheng et al., 2002; Sanchez and deRossi, 1996; Yang et al., 1996; Suzuki et al., 1991). The association with CDs of azobenzene-containing chains adds further degrees of complexity (interaction between CDs and nonazo monomers can be attractive or repulsive) to the intrachain interactions. The association of CDs with the chain may depend on the E Z isomerisation. It was found that aCD and bCDs are best suited than larger CDs to discriminate the E and Z isomers of azobenzene. Naturally, the association of CD modi es the enthalpy of chain folding and collapsing, by masking the hydrophobes in CD cavities, and adding CD-monomers contacts and steric hampering to conformational freedom. All these effects contribute to chain swelling or collapse. The common interpretation of photoresponses in the presence of CDs invokes that the trans isomer associates tightly into the CD cavities, whereas the cis isomer does not bind (Zheng et al., 2004; RodriguezCabello et al., 2002; Ueno et al., 2002). Measurements by NMR and circular dichroism validate this point in some systems containing aCD (Tomatsu et al., 2006; Zheng et al., 2005). In general, things are less obvious, and CDs (especially bCD) may partially dissociate upon transconversion to the cis form, or bind to both the E and Z forms of azobenzene, with a different geometries and stoichiometries (Fig. 7.3a; Inoue et al., 2007; Pouliquen et al., 2007; Tomatsu et al., 2006). Both phenomena make nevertheless the azo-modi ed chains more hydrophilic in presence of CDs (upper shift of LCSTs). The dark-adapted (trans) form is even
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CHAPTER 7: ASSOCIATION BETWEEN AZOBENZENE MODIFIED POLYMERS
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100 Transmittance (%) 80 60 40 20 0 10
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30 mM -CD
trans
trans
40 50 Temperature ( C) (b)
Figure 7.3. Effect of CD host guest interaction on azobenzene-modi ed polymers. (a) Drawing of the equilibrium between bound and unbound CDs. With the change of geometry under the cis form approaching the CD toward the backbone, Ktrans may be higher than Kcis. (b) Experimental variation of turbidity and shift of LCST measured in mixtures of hydroxypropyl methylcellulose in the presence or absence of aCD as quoted in the gure. Source: Reprinted with permission from Zheng et al., 2004.
more hydrophilic than the cis one, presumably because of the deeper penetration of the E-form inside the CD cavity. Consequently, the coef cient aUV atrans in Equation 7.1 can become negative. In such mixed systems, the rst stage of ampli cation is achieved by recognition of azobenzene s isomers at the molecular scale. The second ampli cation stage is brought by chain collapsing in poor solvent. The development of new photocomplexing agents coupled with chain collapsing could certainly help design systems with a large temperature range of photoresponsiveness.