A red-shifted two-photon-only caging group for three-dimensional photorelease?

Chemical Science Pub Date: 2018-02-09 DOI: 10.1039/C7SC05182D

Abstract

Based on nitrodibenzofuran (NDBF) a new photocage with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visualized via double-strand displacement in a hydrogel. With this assay we achieved three-dimensional photorelease of DMA-NDBF-protected DNA orthogonal to NDBF-protected strands. While being an excellent 2P-cage, DMA-NDBF is surprisingly stable under visible-light one-photon excitation (1PE). This case of excitation-specific photochemistry enhances the scope of orthogonal photoregulation.

Graphical abstract: A red-shifted two-photon-only caging group for three-dimensional photorelease
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