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The role of alkyl substituents in deazaadenine-based diarylethene photoswitches

Diarylethenes are an important class of reversible photoswitches and often claimed to require two alkyl substituents at the carbon atoms between which the bond is formed or broken in the electrocyclic rearrangement. Here we probe this claim by the synthesis and characterization of four pairs of deaz...

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Autores principales: Sarter, Christopher, Heimes, Michael, Jäschke, Andres
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901873/
https://www.ncbi.nlm.nih.gov/pubmed/27340498
http://dx.doi.org/10.3762/bjoc.12.106
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author Sarter, Christopher
Heimes, Michael
Jäschke, Andres
author_facet Sarter, Christopher
Heimes, Michael
Jäschke, Andres
author_sort Sarter, Christopher
collection PubMed
description Diarylethenes are an important class of reversible photoswitches and often claimed to require two alkyl substituents at the carbon atoms between which the bond is formed or broken in the electrocyclic rearrangement. Here we probe this claim by the synthesis and characterization of four pairs of deazaadenine-based diarylethene photoswitches with either one or two methyl groups at these positions. Depending on the substitution pattern, diarylethenes with one alkyl group can exhibit significant photochromism, but they generally show poor stability towards extended UV irradiation, low thermal stability, and decreased fatigue resistance. The results obtained provide an important direction for the design of new efficient DNA photoswitches for the application in bionanotechnology and synthetic biology.
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spelling pubmed-49018732016-06-23 The role of alkyl substituents in deazaadenine-based diarylethene photoswitches Sarter, Christopher Heimes, Michael Jäschke, Andres Beilstein J Org Chem Full Research Paper Diarylethenes are an important class of reversible photoswitches and often claimed to require two alkyl substituents at the carbon atoms between which the bond is formed or broken in the electrocyclic rearrangement. Here we probe this claim by the synthesis and characterization of four pairs of deazaadenine-based diarylethene photoswitches with either one or two methyl groups at these positions. Depending on the substitution pattern, diarylethenes with one alkyl group can exhibit significant photochromism, but they generally show poor stability towards extended UV irradiation, low thermal stability, and decreased fatigue resistance. The results obtained provide an important direction for the design of new efficient DNA photoswitches for the application in bionanotechnology and synthetic biology. Beilstein-Institut 2016-06-01 /pmc/articles/PMC4901873/ /pubmed/27340498 http://dx.doi.org/10.3762/bjoc.12.106 Text en Copyright © 2016, Sarter et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Sarter, Christopher
Heimes, Michael
Jäschke, Andres
The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
title The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
title_full The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
title_fullStr The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
title_full_unstemmed The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
title_short The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
title_sort role of alkyl substituents in deazaadenine-based diarylethene photoswitches
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901873/
https://www.ncbi.nlm.nih.gov/pubmed/27340498
http://dx.doi.org/10.3762/bjoc.12.106
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