Robust Red-Absorbing Donor-Acceptor Stenhouse Adduct Photoswitches
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Donor-Acceptor Stenhouse Adduct (DASA), a class of push-pull negative photochrome, has received large interest lately owing to its versatile synthesis, modularity and excellent photoswitching in solutions. From a technological perspective, it is imperative for this class of photoswitches to work robustly in solid state, e. g. thin films. We feature a molecular framework for the optimized design of DASAs by introducing a new thioindoline donor (D3) and assessing its performance against known 2nd generation indoline-based donors. The systematic structure-function investigations suggest that to achieve robust reversible photoswitching, a ground state with low charge separation is desired. DASAs with stronger electron donors and a larger charge separation in the ground state result in a low population of the photothermalstationary state (PTSS) and reduced photostability. The DASA with thioindoline donor (D3A3) seems to be a special case among the donor series as it causes a red shift (ca. 15 nm), however with less polarization of the ground state and marginally better photostability as compared to the unsubstituted 2-methyl indoline (D1A3). We also emphasize the consideration of the key additional factors that can modulate the red-light photoswitching properties of DASA chromophores in polymer thin films, which might not be dominant in homogenous solution state.
Original language | English |
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Article number | e202400621 |
Journal | Chemistry - A European Journal |
ISSN | 0947-6539 |
DOIs | |
Publication status | E-pub ahead of print - 2024 |
Bibliographical note
Funding Information:
Authors acknowledge the financial support from the European Union, Horizon Europe, Project 101046790 \u2013 InsectNeuroNano.
Publisher Copyright:
© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
- Donor-Acceptor Stenhouse Adducts, Photoswitches, Polymer Thin Films, Red-Light Photoswitching, Structure-Function Relationship
Research areas
ID: 391116378