Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages
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- Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages_(accepted_version)
Accepted author manuscript, 1.82 MB, PDF document
Photoswitchable small molecules, such as N , N'- disubstituted indigos, have received great interest within fields such as pharmacology, energy storage, and functional materials, as they represent key building blocks for reversible and non-invasive control of chemical processes. However, to ensure applicability of photochromic systems it is of paramount importance to manipulate the photostationary state. In this work, we achieved this by tethering two redox-active indenofluorene-extended tetrathiafulvalene units to an N , N' -disubstituted indigo photoswitch. Upon two-electron oxidation, we observe significantly enhanced stability of the Z -isomer, compared to the neutral compound, illustrated by a substantial increase in the half-life from 0.48 seconds to 22 hours. This remarkable stabilization is ascribed to formation of strong, intramolecular pi-dimers between the oxidized subunits.
Original language | English |
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Journal | European Journal of Organic Chemistry |
Volume | 2021 |
Issue number | 46 |
Pages (from-to) | 6304-6311 |
Number of pages | 8 |
ISSN | 1099-0690 |
DOIs | |
Publication status | Published - 2 Sep 2021 |
- Cross-coupling, Fused-ring systems, Photochromism, sulfur heterocycles, Supramolecular chemistry
Research areas
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