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Photoisomerization of azobenzene

In chemistry, photoisomerization is a molecular behavior in which structural change between isomers is caused by photoexcitation.[1] Both reversible and irreversible isomerization reactions exist. However, the word "photoisomerization" usually indicates a reversible process.


Photoisomerizable molecules are already put to practical use, for instance, in pigments for rewritable CDs, DVDs, and 3D optical data storage solutions. In fact, photoisomerization of the molecule retinal in the eye is the mechanism that allows for vision. In addition, recent interest in photoisomerizable molecules has been aimed at molecular devices, such as molecular switches,[2][3] molecular motors,[4] and molecular electronics.


Photoisomerization behavior can be roughly categorized into several classes. Two major classes are trans-cis (or 'E-'Z) conversion, and open-closed ring transition. Examples of the former include stilbene and azobenzene. This type of compounds has a double bond, and rotation or inversion around the double bond affords isomerization between the two states. Examples of the latter include fulgide and diarylethene. This type of compounds undergoes bond cleavage and bond creation upon irradiation with particular wavelengths of light. Still another class is the di-pi-methane rearrangement.

See also[edit]


  1. ^ "Photoisomerization". 2009. doi:10.1351/goldbook.P04622.
  2. ^ Mammana, A.; et al. (2011). "A Chiroptical Photoswitchable DNA Complex". Journal of Physical Chemistry B. 115 (40): 11581–11587. doi:10.1021/jp205893y.
  3. ^ Mokdad, A; Belof, J; Yi, S; Shuler, S; McLaughlin, M; Space, B; Larsen, R (2008). "Photophysical Studies of the Trans to Cis Isomerization of the Push−Pull Molecule: 1-(Pyridin-4-yl)-2-(N-methylpyrrol-2-yl)ethene (mepepy)". Journal of Physical Chemistry B. 112 (36): 8310–8315. Bibcode:2008JPCA..112.8310M. doi:10.1021/jp803268r.
  4. ^ Vachon, J.; et al. (2014). "An ultrafast surface-bound photo-active molecular motor". Photochemical and Photobiological Sciences. 13 (2): 241–246. doi:10.1039/C3PP50208B.