λ-orthogonal pericyclic macromolecular photoligation
Hiltebrandt, Kai, Pauloehrl, Thomas, Blinco, James P., Linkert, Katharina, Börner, Hans G., & Barner-Kowollik, Christopher (2015) λ-orthogonal pericyclic macromolecular photoligation. Angewandte Chemie International Edition, 54(9), pp. 2838-2843.
A photochemical strategy enabling λ-orthogonal reactions is introduced to construct macromolecular architectures and to encode variable functional groups with site-selective precision into a single molecule by the choice of wavelength. λ-Orthogonal pericyclic reactions proceed independently of one another by the selection of functional groups that absorb light of specific wavelengths. The power of the new concept is shown by a one-pot reaction of equimolar quantities of maleimide with two polymers carrying different maleimide-reactive endgroups, that is, a photoactive diene (photoenol) and a nitrile imine (tetrazole). Under selective irradiation at λ=310–350 nm, any maleimide (or activated ene) end-capped compound reacts exclusively with the photoenol functional polymer. After complete conversion of the photoenol, subsequent irradiation at λ=270–310 nm activates the reaction of the tetrazole group with functional enes. The versatility of the approach is shown by λ-orthogonal click reactions of complex maleimides, functional enes, and polymers to the central polymer scaffold.
Impact and interest:
Citation counts are sourced monthly from and citation databases.
These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.
Citations counts from theindexing service can be viewed at the linked Google Scholar™ search.
|Item Type:||Journal Article|
|Keywords:||click reaction, orthogonal reactivity, photochemistry, photoenol, tetrazole|
|Subjects:||Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MACROMOLECULAR AND MATERIALS CHEMISTRY (030300)
Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MACROMOLECULAR AND MATERIALS CHEMISTRY (030300) > Synthesis of Materials (030306)
|Divisions:||Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
|Deposited On:||31 Mar 2015 23:29|
|Last Modified:||02 Apr 2015 02:58|
Repository Staff Only: item control page