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Hydrophilic
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Hydrophobic
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trans-azo (small dipole moment)
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cis-azo (large dipole moment)
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Light
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Figure 6.1. Schematic illustration of light-controllable micelles and vesicles formed by azobenzene-containing block copolymers displaying the trans cis photoisomerization. See color insert.
CHAPTER 6: AZOBENZENE CONTAINING BLOCK COPOLYMER MICELLES
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moment for the trans isomer than the cis isomer (Simmons et al., 2007), should not be used because of the opposite change in dipole moment upon UV light illumination. Another consideration also does not favor the use of azobenzene derivatives with strong electron-donor and electron-acceptor groups. This pattern of substitution on azobenzene usually results in overlap of the absorption of transazobenzene (p-p*) with that of cis-azobenzene (n-p*), in the 440 460 nm region. Not only does the cis isomer have a fast thermally activated relaxation back to the trans isomer, photons absorbed by trans-azobenzene, inducing the trans cis isomerization, can also be signi cantly absorbed by cis-azobenzene that induces the reverse cis trans isomerization. The consequence of the fast thermal relaxation of cisazobenzene and the simultaneous photoisomerization in the two directions is that few azobenzene moieties in the cis form can stay. Obviously, for light-controllable polymer micelles, a bistable photoswitch is preferred. As far as azobenzene is concerned, its derivatives that can undergo a thorough trans cis isomerization upon UV light illumination and have thermally stable cis isomer are mostly interesting. From the above analysis, using azobenzene BCPs, a signi cant increase in dipole moment accompanying the trans cis isomerization of the chromophore under UV light can increase the entire polarity of the hydrophobic polymer block and, consequently, shift the hydrophilic hydrophobic balance in the direction thermodynamically unfavorable to the micellar association. Although the micellar association is very sensitive to the balance, such a shift may not be necessarily enough to cause the dissociation of BCP micelles; other factors need to be taken into consideration. This can be illustrated using a classical small-molecule surfactant as example. The anionic surfactants of CH3(CH2)nNHCOO has a cmc sensitive to the hydrophilic hydrophobic balance; the cmc is 1.8 10 4 mol dm 3 for n=13, while it is reduced by an order to 1.8 10 5 mol dm 3 for n=15 (longer hydrocarbon tail) (Everett DH, 1988). Now, imagine a micellar solution of the surfactant with n=15 exposed to light, if somehow two methylene groups were removed from the hydrocarbon tail, the micelles would be dissociated if the surfactant concentration in solution was below 1.8 10 4 mol dm 3 (cmc of the surfactant with n=13), while they would remain if the surfactant concentration was above this cmc. This simple example points to the fact that an important shift in the hydrophilic hydrophobic balance alone may not be enough to result in the dissociation of the micelles and that other conditions need to be ful lled. As will be discussed later, this indeed is the case for the micelles formed by azobenzenecontaining BCPs. In order to achieve an effective dissociation under UV light, a signi cant increase in the dipole moment for azobenzene while converting from the trans to the cis isomer should be conjugated with a hydrophilic block that is weakly hydrophilic, yet enough to induce the formation of BCP micelles in a selective solvent (Tong et al., 2005). The rst BCP micelles exhibiting reversible light-induced control in dissociation and formation were prepared using azobenzene BCPs (Tong et al., 2005; Wang et al., 2004). More important is the fact that inspired by the principles revealed from these studies on azobenzene BCPs using other chromophores, photosensitive BCP micelles with more effective light-induced
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6.3. SYNTHESIS OF AZOBENZENE CONTAINING AMPHIPHILIC
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dissociation were obtained, and light-controlled release of model compounds loaded in the micelles was also demonstrated (Lee et al., 2007; Jiang et al., 2006, 2005). To achieve more straightforward destabilization of BCP micelles upon illumination, the hydrophobic block can be designed to bring a chromophore as pendant groups, whose photoreaction such as photocleavage (Jiang et al., 2006, 2005) and isomerization (Lee et al., 2007) simply transforms the hydrophobic block to a hydrophilic one. This obviously leads to the dissociation of BCP micelles since the amphiphilicity required for the micellar association is gone. The same strategy has also been extended by Zhang s group to amphiphiles composed of a polymer and a photosensitive chromophore to make photodissociable vesicles (Jiang et al., 2007). In principle, azobenzene moieties can also be incorporated into the structure of the hydrophilic block of amphiphilic BCPs. Synthetically speaking, it may be more dif cult, but it is feasible by using, for example, azobenzene-containing polyelectrolytes as the hydrophilic block. However, if the trans cis photoisomerization under UV light irradiation results in an increase in dipole moment of azobenzene, the increased polarity of the hydrophilic block obviously cannot destabilize the micelles. Using appropriate substitution patterns for azobenzene, the trans cis isomerization can lead to a decrease in dipole moment of azobenzene. The resulting decrease in polarity of the hydrophilic block can eventually shift the hydrophilic hydrophobic balance in the direction unfavorable for BCP micelles. This may result in either morphological changes of the micellar aggregates or simply precipitation of the polymer if the hydrophilicity of the hydrophilic block can no longer ensure the solubility or the stability of the aggregates. Clearly, in the context of polymer nanocarriers for controlled delivery applications, it would be less interesting to use hydrophilic blocks carrying azobenzene moieties.
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