Visible light-induced single bond rotation in azoarenes triggered by self-sensitized oxidation
- 1Institut für Organische Chemie, Universität Duisburg-Essen, Universitätsstr. 7 D-45117 Essen Germany
Abstract
Controlled molecular motion is a cornerstone of both biological function and artificial dynamic systems. While light-induced isomerization of double bonds is well-established, selective rotation around single bonds without concurrent double bond isomerization remains largely unexplored. Here, we present a class of chalcogen-substituted azoarenes that undergo light-induced N–C single bond rotation, independent of N
Created by potrace 1.16, written by Peter Selinger 2001-2019
N isomerization. This rotation is triggered by self-sensitized photooxidation of an ortho-tellurium center, which switches the preferred binding site of a β-hydroxy group from the azo unit to the tellurium σ hole. Experimental evidence from UV/Vis and NMR spectroscopy, supported by quantum chemical calculations, confirms the light-induced rotation and its complete reversibility upon chemical reduction. Importantly, the process is accessible under both UV and sunlight. This study establishes a new mechanism for directing molecular motion, offering a versatile strategy for designing photo- and redox-responsive molecular switches.
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BibTeX
@article{scheller2026visible,
title = {{Visible light-induced single bond rotation in azoarenes triggered by self-sensitized oxidation}},
author = {Zoe Nonie Scheller and Jan Schulte and Christoph Wölper and Gebhard Haberhauer},
journal = {Chemical Science},
year = {2026},
month = sep,
doi = {10.1039/d6sc06305e},
url = {https://doi.org/10.1039/d6sc06305e},
note = {CC BY 3.0},
}
RIS
TY - JOUR
TI - Visible light-induced single bond rotation in azoarenes triggered by self-sensitized oxidation
AU - Zoe Nonie Scheller
AU - Jan Schulte
AU - Christoph Wölper
AU - Gebhard Haberhauer
PY - 2026
DA - 2026/09/15
JO - Chemical Science
DO - 10.1039/d6sc06305e
UR - https://doi.org/10.1039/d6sc06305e
AB - Controlled molecular motion is a cornerstone of both biological function and artificial dynamic systems. While light-induced isomerization of double bonds is well-established, selective rotation around single bonds without concurrent double bond isomerization remains largely unexplored. Here, we present a class of chalcogen-substituted azoarenes that undergo light-induced N–C single bond rotation, independent of N Created by potrace 1.16, written by Peter Selinger 2001-2019 N isomerization. This rotation is triggered by self-sensitized photooxidation of an ortho-tellurium center, which switches the preferred binding site of a β-hydroxy group from the azo unit to the tellurium σ hole. Experimental evidence from UV/Vis and NMR spectroscopy, supported by quantum chemical calculations, confirms the light-induced rotation and its complete reversibility upon chemical reduction. Importantly, the process is accessible under both UV and sunlight. This study establishes a new mechanism for directing molecular motion, offering a versatile strategy for designing photo- and redox-responsive molecular switches.
SN - 2041-6520
SN - 2041-6539
ER -