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

Yvonne Becker; Erik Unger; Manuela A. H. Fichte; Daniel A. Gacek; Andreas Dreuw; Josef Wachtveitl; Peter J. Walla; Alexander Heckel

doi:10.1039/C7SC05182D

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

Yvonne Becker,‡^a Erik Unger,‡^a Manuela A. H. Fichte,^a Daniel A. Gacek,

^b Andreas Dreuw,

^c Josef Wachtveitl,

^d Peter J. Walla^b and Alexander Heckel

*^a

Author affiliations

* Corresponding authors

^a Goethe University Frankfurt, Institute for Organic Chemistry and Chemical Biology, Max-von-Laue-Str. 7, 60438 Frankfurt, Germany
E-mail: heckel@uni-frankfurt.de

^b Technical University Braunschweig, Institute for Physical and Theoretical Chemistry, Gaußstr. 17, 38106 Braunschweig, Germany

^c Interdisciplinary Center for Scientific Computing (IWR), Theoretical and Computational Chemistry, Im Neuenheimer Feld 205A, 69120 Heidelberg, Germany

^d Goethe University Frankfurt, Institute for Physical and Theoretical Chemistry, Max-von-Laue-Str. 7, 60438 Frankfurt, Germany

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.

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DOI: https://doi.org/10.1039/C7SC05182D
Article type: Edge Article
Submitted: 06 Dec 2017
Accepted: 08 Feb 2018
First published: 09 Feb 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2018,9, 2797-2802

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

Y. Becker, E. Unger, M. A. H. Fichte, D. A. Gacek, A. Dreuw, J. Wachtveitl, P. J. Walla and A. Heckel, Chem. Sci., 2018, 9, 2797 DOI: 10.1039/C7SC05182D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Science

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

Abstract

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

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