An investigation into the photochemical properties of cyclized-Azobenzene photoswitches.

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Abstract Summary


Molecular photoswitches are playing increasingly central roles in interrogating the functions of chemical systems by allowing for selective conversion between two distinct states [1]. With applications in fields including but not limited to; neurobiology [2], chemical synthesis, and even branching into material science, the potential for novel discovery is expanding and variations of implementations are becoming realizable. Molecular photoswitches allow for precise spatial rearrangement of atoms in time, they are being used to interrogate systems by selectively initializing highly energetic reactions within systems, which otherwise would prove difficult to execute. 

Azobenzene derivatives specifically have garnered great interest for their well understood photochemical properties and reasonable incorporation into other chemistries. However, where prototypical azo-units have fallen short in performing, cyclized-Azobenzene’s are picking up the slack with their distinguished absorption bands and long relaxation rates. Not only are these cyclized motif’s an improvement in selectivity and stability, but they have the added benefit of incorporating a degree of ring strain, which is yet another functional property that can be explored and exploited to overcome energetic barriers of reactions. Thus, with slight modifications to a molecular species of interest[2], there may be a means to not only initiate high-energy reactions, but to do so at precise sites within molecules, and thus paving the way for new types of synthetic control. 

Potential future application includes; tethered biological-receptor-substrate’s, a responsive handle for labeled moieties, and potentially even use in novel syntheses of various photo-responsive polymers.



[1] Siewertsen, Ron, et al. “Highly Efficient Reversible Z−E Photoisomerization of a Bridged Azobenzene with Visible Light through Resolved S1(Nπ*) Absorption Bands.” Journal of the American Chemical Society, vol. 131, no. 43, 2009, pp. 15594–15595.


[2] Thapaliya, Ek Raj, et al. “Locked-Azobenzene: Testing the Scope of a Unique Photoswitchable Scaffold for Cell Physiology.” ACS Chemical Neuroscience, 2019, 

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