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Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths
Diazocines are bridged azobenzenes with phenyl rings connected by a CH(2)–CH(2) group. Despite this rather small structural difference, diazocine exhibits improved properties over azobenzene as a photoswitch and most importantly, its Z configuration is more stable than the E isomer. Herein, we revea...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10466275/ https://www.ncbi.nlm.nih.gov/pubmed/37655019 http://dx.doi.org/10.1039/d3sc02681g |
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author | Isokuortti, Jussi Griebenow, Thomas von Glasenapp, Jan-Simon Raeker, Tim Filatov, Mikhail A. Laaksonen, Timo Herges, Rainer Durandin, Nikita A. |
author_facet | Isokuortti, Jussi Griebenow, Thomas von Glasenapp, Jan-Simon Raeker, Tim Filatov, Mikhail A. Laaksonen, Timo Herges, Rainer Durandin, Nikita A. |
author_sort | Isokuortti, Jussi |
collection | PubMed |
description | Diazocines are bridged azobenzenes with phenyl rings connected by a CH(2)–CH(2) group. Despite this rather small structural difference, diazocine exhibits improved properties over azobenzene as a photoswitch and most importantly, its Z configuration is more stable than the E isomer. Herein, we reveal yet another unique feature of this emerging class of photoswitches. In striking contrast to azobenzenes and other photochromes, diazocine can be selectively switched in E → Z direction and most intriguingly from its thermodynamically stable Z to metastable E isomer upon successive excitation of two different triplet sensitizers present in solution at the same time. This approach leads to extraordinary large redshift of excitation wavelengths to perform isomerization i.e. from 400 nm blue to 530 nm green light (Z → E) and from 530 nm green to 740 nm far-red one (E → Z), which falls in the near-infrared window in biological tissue. Therefore, this work opens up of potential avenues for utilizing diazocines for example in photopharmacology, smart materials, light energy harvesting/storage devices, and out-of-equilibrium systems. |
format | Online Article Text |
id | pubmed-10466275 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-104662752023-08-31 Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths Isokuortti, Jussi Griebenow, Thomas von Glasenapp, Jan-Simon Raeker, Tim Filatov, Mikhail A. Laaksonen, Timo Herges, Rainer Durandin, Nikita A. Chem Sci Chemistry Diazocines are bridged azobenzenes with phenyl rings connected by a CH(2)–CH(2) group. Despite this rather small structural difference, diazocine exhibits improved properties over azobenzene as a photoswitch and most importantly, its Z configuration is more stable than the E isomer. Herein, we reveal yet another unique feature of this emerging class of photoswitches. In striking contrast to azobenzenes and other photochromes, diazocine can be selectively switched in E → Z direction and most intriguingly from its thermodynamically stable Z to metastable E isomer upon successive excitation of two different triplet sensitizers present in solution at the same time. This approach leads to extraordinary large redshift of excitation wavelengths to perform isomerization i.e. from 400 nm blue to 530 nm green light (Z → E) and from 530 nm green to 740 nm far-red one (E → Z), which falls in the near-infrared window in biological tissue. Therefore, this work opens up of potential avenues for utilizing diazocines for example in photopharmacology, smart materials, light energy harvesting/storage devices, and out-of-equilibrium systems. The Royal Society of Chemistry 2023-08-08 /pmc/articles/PMC10466275/ /pubmed/37655019 http://dx.doi.org/10.1039/d3sc02681g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Isokuortti, Jussi Griebenow, Thomas von Glasenapp, Jan-Simon Raeker, Tim Filatov, Mikhail A. Laaksonen, Timo Herges, Rainer Durandin, Nikita A. Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
title | Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
title_full | Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
title_fullStr | Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
title_full_unstemmed | Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
title_short | Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
title_sort | triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10466275/ https://www.ncbi.nlm.nih.gov/pubmed/37655019 http://dx.doi.org/10.1039/d3sc02681g |
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