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Beilstein J Org Chem. 2012;8:2184-90. doi: 10.3762/bjoc.8.246. Epub 2012 Dec 14.

A bisazobenzene crosslinker that isomerizes with visible light.

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  • 1Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6, Canada; telephone: (416) 978-0675, fax: (416) 978-8775.

Abstract

BACKGROUND:

Large conformational and functional changes of azobenzene-modified biomolecules require longer azobenzene derivatives that undergo large end-to-end distance changes upon photoisomerization. In addition, isomerization that occurs with visible rather than UV irradiation is preferred for biological applications.

RESULTS:

We report the synthesis and characterization of a new crosslinker in which a central piperazine unit links two azobenzene chromophores. Molecular modeling indicates that this crosslinker can undergo a large change in end-to-end distance upon trans,trans to cis,cis isomerization. Photochemical characterization indicates that it does isomerize with visible light (violet to blue wavelengths). However, the thermal relaxation rate of this crosslinker is rather high (τ(½) ~ 1 s in aqueous buffer at neutral pH) so that it is difficult to produce large fractions of the cis,cis-species without very bright light sources.

CONCLUSION:

While cis-lifetimes may be longer when the crosslinker is attached to a biomolecule, it appears the para-piperazine unit may be best suited for applications where rapid thermal relaxation is required.

KEYWORDS:

azobenzene; molecular switches; photo-control; switch; visible

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