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- Title
Stabilizing Indigo Z‐Isomer through Intramolecular Associations of Redox‐Active Appendages.
- Authors
Broløs, Line; Klaue, Kristin; Bendix, Jesper; Grubert, Lutz; Hecht, Stefan; Nielsen, Mogens Brøndsted
- Abstract
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 π‐dimers between the oxidized subunits.
- Subjects
INDIGO; CHEMICAL process control; SMALL molecules; TETRATHIAFULVALENE; ENERGY storage
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 46, p6304
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202100781