Anion‐Receptive Triazine‐Centered Azobenzene Trimers
Abstract
Triazine‐centered C 3 ‐symmetric azobenzene trimers were synthesized using complementary azo‐forming strategies, providing a versatile platform for multiresponsive molecular photoswitches. Relative to the isoelectronic benzonitrile monomer, incorporation of the triazine core induces an intrinsic bathochromic shift of the azobenzene absorption bands. The thiomethoxy‐substituted derivative exhibits negative photochromism, enabling efficient trans–cis photoisomerization with wavelengths up to 525 nm. Combined temperature‐dependent operando UV/vis spectroscopy and DFT calculations reveal thermal cis–trans isomerization kinetics consistent with a triplet‐assisted rotational pathway. Evaluation of transmission coefficients exposes pronounced solvent‐friction effects, demonstrating that substituent‐controlled solute–solvent coupling governs thermal half‐lives beyond barrier heights. In addition, the electron‐deficient triazine core enables anion binding that induces intramolecular charge‐transfer absorption and modulates thermal relaxation, introducing triazine‐centered azobenzenes as supramolecular multistimuli‐responsive photoswitches.
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BibTeX
@article{ayadi2026anionreceptive,
title = {{Anion‐Receptive Triazine‐Centered Azobenzene Trimers}},
author = {Awatef Ayadi and Atiur Rahaman and Quentin Deborde and Valentin Magné and Orein Jafter and Dominik Lungerich},
journal = {European Journal of Organic Chemistry},
year = {2026},
month = jul,
doi = {10.1002/ejoc.70669},
url = {https://hal.science/hal-05774552v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Anion‐Receptive Triazine‐Centered Azobenzene Trimers
AU - Awatef Ayadi
AU - Atiur Rahaman
AU - Quentin Deborde
AU - Valentin Magné
AU - Orein Jafter
AU - Dominik Lungerich
PY - 2026
DA - 2026/07/12
JO - European Journal of Organic Chemistry
DO - 10.1002/ejoc.70669
UR - https://hal.science/hal-05774552v1
AB - Triazine‐centered C 3 ‐symmetric azobenzene trimers were synthesized using complementary azo‐forming strategies, providing a versatile platform for multiresponsive molecular photoswitches. Relative to the isoelectronic benzonitrile monomer, incorporation of the triazine core induces an intrinsic bathochromic shift of the azobenzene absorption bands. The thiomethoxy‐substituted derivative exhibits negative photochromism, enabling efficient trans–cis photoisomerization with wavelengths up to 525 nm. Combined temperature‐dependent operando UV/vis spectroscopy and DFT calculations reveal thermal cis–trans isomerization kinetics consistent with a triplet‐assisted rotational pathway. Evaluation of transmission coefficients exposes pronounced solvent‐friction effects, demonstrating that substituent‐controlled solute–solvent coupling governs thermal half‐lives beyond barrier heights. In addition, the electron‐deficient triazine core enables anion binding that induces intramolecular charge‐transfer absorption and modulates thermal relaxation, introducing triazine‐centered azobenzenes as supramolecular multistimuli‐responsive photoswitches.
SN - 1434-193X
SN - 1099-0690
ER -