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Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

Jannis Ludwig, Tobias Moje, Fynn Röhricht and Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2589–2597. https://doi.org/10.3762/bjoc.16.210

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Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

Jannis Ludwig, Tobias Moje, Fynn Röhricht and Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2589–2597. https://doi.org/10.3762/bjoc.16.210

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Ludwig, J.; Moje, T.; Röhricht, F.; Herges, R. Beilstein J. Org. Chem. 2020, 16, 2589–2597. doi:10.3762/bjoc.16.210

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TY  - JOUR
A1  - Ludwig, Jannis
A1  - Moje, Tobias
A1  - Röhricht, Fynn
A1  - Herges, Rainer
T1  - Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches
JF  - Beilstein Journal of Organic Chemistry
PY  - 2020///
VL  - 16
SP  - 2589
EP  - 2597
SN  - 1860-5397
DO  - 10.3762/bjoc.16.210
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.16.210
KW  - azopyridines
KW  - Ni(II)-porphyrins
KW  - photoswitch
KW  - record player molecules
KW  - spin state
KW  - spin switch
N2  - We present the synthesis and the spin switching efficiencies of Ni(II)-porphyrins substituted with azopyridines as covalently attached photoswitchable ligands. The molecules are designed in such a way that the azopyridines coordinate to the Ni ion if the azo unit is in cis configuration. For steric reasons no intramolecular coordination is possible if the azopyridine unit adopts the trans configuration. Photoisomerization of the azo unit between cis and trans is achieved upon irradiation with 505 nm (trans→cis) and 435 nm (cis→trans). Concurrently with the isomerization and coordination/decoordination, the spin state of the Ni ion switches between singlet (low-spin) and triplet (high-spin). Previous studies have shown that the spin switching efficiency is strongly dependent on the solvent and on the substituent at the 4-position of the pyridine unit. We now introduced thiol, disulfide, thioethers, nitrile and carboxylic acid groups and investigated their spin switching efficiency.
ER  -

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Gupta, D.; Gaur, A. K.; Kumar, H.; Singh, S.; Venkataramani, S. Light‐Switchable Metal Complexes: Introducing Photoresponsive Behaviour Through Azoheteroarenes. ChemPhotoChem 2023, 7. doi:10.1002/cptc.202300068
Orvoš, J.; Pančík, F.; Fischer, R. Facile One‐Step Oxidation of N‐Boc‐Protected Diarylhydrazines to Diaryldiazenes with (Diacetoxyiodo)benzene under Mild Conditions. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300049
Fischer, K.; Krahmer, J.; Tuczek, F. Chemically and Light-Driven Coordination-Induced Spin State Switching (CISSS) of a nonheme-iron complex. Zeitschrift für Naturforschung B 2022, 77, 299–311. doi:10.1515/znb-2022-0011
Wang, Y.; Iglesias, D.; Gali, S. M.; Beljonne, D.; Samorì, P. Light-Programmable Logic-in-Memory in 2D Semiconductors Enabled by Supramolecular Functionalization: Photoresponsive Collective Effect of Aligned Molecular Dipoles. ACS nano 2021, 15, 13732–13741. doi:10.1021/acsnano.1c05167

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