Azobenzene

Azobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond.

[5] Different classes of azo dyes exist, most notably the ones substituted with heteroaryl rings.

These azos are yellow, orange, and red, respectively,[15][16] owing to the subtle differences in their electronic absorption spectra.

Azos that are ortho- or para-substituted with electron-donating groups (such as aminos), are classified as aminoazobenzenes, and tend to closely spaced[15] n-π* and π-π* bands in the visible.

The pseudo-stilbene class is characterized by substituting the 4 and 4' positions of the two azo rings with electron-donating and electron-withdrawing groups (that is, the two opposite ends of the aromatic system are functionalized).

The addition of this push-pull configuration results in a strongly asymmetric electron distribution, which modifies a host of optical properties.

[16] Thus, for these compounds a single wavelength of light in the visible region will induce both the forward and reverse isomerization.

The rate of the thermal back-relaxation varies greatly depending on the compound: usually hours for azobenzene-type molecules, minutes for aminoazobenzenes, and seconds for the pseudo-stilbenes.

There is experimental and computational evidence for the existence of a multistate rotation mechanism involving a triplet state.

[21] However, those relaxed (trans) molecules that fall perpendicular to the incoming light polarization will no longer be able to absorb, and will remain fixed.

Skeletal formula of azobenzene
Skeletal formula of azobenzene
Ball-and-stick model of azobenzene
Ball-and-stick model of azobenzene
X-ray crystallography reveals the highly nonplanar, twisted structure for cis -azobenzene.
Azobenzene photoisomerization . The trans form (left) can be converted to the cis form (right) using a UV wavelength of 300–400 nm. Visible illumination at >400 nm converts the molecule back to the trans form. Alternately, the molecule will thermally relax to the stable trans form.
Photoisomerization of methoxyazobenzene results in reversible color change