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Irradiation with light produces molecular changes in azobenzenes, and under appropriate conditions, these changes can translate into larger scale motions and even modulation of material properties. Following Natansohn and Rochon (2002), we will describe motions roughly in order of increasing size scale. However, since the motion on any size scale invariably affects (and is affected by)
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other scales, clear divisions are not possible. In all cases, some of the implicated applications, photoswitching, and photomodulations will be outlined.
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1.2.1. Molecular Motion
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The fundamental molecular photomotion in azobenzenes is the geometrical change that occurs on absorption of light. In cis-azobenzene, the phenyl rings are twisted at 901 relative to the C N=N C plane (Naito et al., 1991; Uznanski et al., 1991). Isomerization reduces the distance between the 4 and 4u positions from 0.99 nm in the trans state to 0.55 nm in the cis state (Brown, 1966; Hampson and Robertson, 1941; de Lange et al., 1939). This geometric change increases the dipole moment: whereas the trans form has no dipole moment, the cis form has a dipole moment of 3.1 D (Hartley, 1937). The free volume requirement of the cis is larger than that of the trans (Naito et al., 1993), and it has been estimated that the minimum free volume pocket required to allow isomerization to proceed via the inversion pathway (Naito et al., 1991; Paik and Morawetz, 1972) is 0.12 nm3, and B0.38 nm3 via the rotation pathway (Lamarre and Sung, 1983). The effects of matrix free volume constraints on photochemical reactions in general have been considered (Weiss et al., 1993). The geometrical changes in azobenzene are very large, by molecular standards, and it is thus no surprise that isomerization modi es a wide host of material properties. This molecular displacement generates a nanoscale force, which has been measured in single-molecule force spectroscopy experiments (Holland et al., 2003; Hugel et al., 2002) and compared with theory (Neuert et al., 2005). In these experiments, illumination causes contraction of an azobenzene polymer, showing that each chromophore can exert pN molecular forces on demand. A pseudorotaxane that can be reversibly threaded dethreaded using light has been called an arti cial molecular-level machine (Balzani et al., 2001; Asakawa et al., 1999). The ability to activate and power molecular-level devices using light is of course attractive since it circumvents the limitations inherent to diffusion or wiring. The fast response and lack of waste products in azo isomerization are also advantageous. Coupling these molecular-scale motions to do useful work is of course the next challenging step. Progress in this direction is evident from a wide variety of molecular switches that have been synthesized. For example, an azo linking two porphyrin rings enabled photocontrol of electron transfer (Tsuchiya, 1999). In another example, dramatically different hydrogen-bonding networks (intermolecular and intramolecular) can be favored on the basis of the isomeric state of the azo group linking two cyclic peptides (Steinem et al., 1999; Vollmer et al., 1999).
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1.2.2. Photobiological Experiments
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The molecular conformation change of the azo chromophore can be used to switch the conformation and hence properties of larger molecular systems to which it is attached. This is particularly interesting in the case of inclusion within molecular-scale biological systems. The bridging of biology and physical
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chemistry is an ever-expanding research domain. It is no surprise that the clean and unique azo photochemistry has been applied to switching biological systems (Willner and Rubin, 1996). One of the earliest investigations of azobenzene in a biological context involved embedding azobenzene molecules into a model membrane system (Balasubramanian et al., 1975). On isomerization, the lamellae were disrupted and rearranged, which also changed the enzymatic activity of membrane-bound proteins. The catalytic activity of a cyclodextrin with a histidine and azobenzene pendant was photocontrollable because the trans version of the azo pendant can bind inside the cyclodextrin pocket, whereas the cis version liberated the catalytic site (Lee and Ueno, 2001). Photoregulation of polypeptide structure has been an active area of research (Ciardelli and Pieroni, 2001), with the azobenzenes making signi cant contributions. Azo-modi ed poly (L-alanine) (Sisido et al., 1991a,b), poly(L-glutamic acid) (Houben et al., 1983; Pieroni et al., 1980), and poly(L-lysine) (Malcolm and Pieroni, 1990), among others, have been prepared. Depending on the system, photoisomerization may cause no change (Houben et al., 1983) or can induce a substantial conformational change, including transitions from ordered chiral helix to disordered achiral chain (Fissi et al., 1996; Yamamoto and Nishida, 1991; Montagnoli et al., 1983), changes in the a-helix content, or even reversible a-helix to b-sheet conversions (Fissi et al., 1987). Also, owing to the change in local electrostatic environment, the pKa of the polypeptides can be controlled in these systems. Covalent attachment of azobenzene units to enzymes can modify protein activity by distorting the protein structure with isomerization. This was used to control the enzyme activity of papain (Willner and Rubin, 1993; Willner et al., 1991a) and the catalytic ef ciency of lysozyme (Inada et al., 2005). A different methodology is to immobilize the protein of interest inside a photoisomerizable copolymer matrix, which was used to control a-chymotrypsin (Willner and Rubin, 1993; Willner et al., 1991b, 1993). The azobenzene need not be directly incorporated into an enzyme of interest. In one case, the activity of tyrosinase could be modi ed by isomerization of small-molecule azo inhibitors (Komori et al., 2004). The photoselective binding of short peptide fragments into enzymes can be used to inhibit, thus control, activity (Harvey and Abell, 2000, 2001). Similarly, the binding of an azopeptide with a monoclonal antibody was found to be photoreversible (Harada et al., 1991). The photoresponse of azobenzene can thus be used to control the availability of key biomolecules. In one case, NAD+ was modi ed with an azobenzene group, and introduced into a mixture with an antibody that binds to the trans form (Hohsaka et al., 1994). This binding makes NAD+ unavailable, whereas irradiation of the solution with UV light induces the trans to cis isomerization, and thereby liberates NAD+. Bioengineering has more recently been broadened by expanding the natural protein alphabet with arti cial amino acids. This enables novel and nonnatural protein sequences to be created, while still exploiting the highly ef cient natural synthesis machinery. Chiral azobenzene amino acids have been synthesized and incorporated into protein sequences (Wang and Schultz, 2004). The introduction of arti cial photoactive residues opens the possibility of
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