Simeth, Nadja A. and Crespi, Stefano and Fagnoni, Maurizio and Koenig, Burkhard (2018) Tuning the Thermal Isomerization of Phenylazoindole Photoswitches from Days to Nanoseconds. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 140 (8). pp. 2940-2946. ISSN 0002-7863,
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The growing interest in light-driven molecular switches and optical oscillators led to the development of molecules that are able to interconvert from a stable to a metastable configuration upon photochemical triggering and to return to the thermodynamically stable form as soon as the light stimulus is removed. Controlling a wide range of back-isomerization lifetimes in the dark is a crucial goal for potential application of these compounds such as molecular machines. We herein present a novel dass of easily synthesizable azo photoswitches based on the arylazoindole core. Most notably, minimal modifications of the core, such as methylation, dramatically change the Z-to-E thermal isomerization rate from days (Me in position 1) to the nanosecond range (Me in position 2). Moreover, fine-tuning of the Z-to-E lifetimes can be achieved choosing a proper dimethyl sulfoxide-water (or buffered water) solvent mixture. The photochemical and thermal mechanisms have been elucidated by a thorough computational and spectroscopic analysis. This allowed to detect three different pathways of thermal isomerization and to identify the hydrazone tautomer of the phenylazoindole actor in the fast Z-E thermal isomerization of the NH-substituted switch in protic media. as the major
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | VISIBLE-LIGHT; AZOBENZENE; PHOTOISOMERIZATION; STATE; ARYLAZOIMIDAZOLES; ARYLAZOPYRAZOLES; SYSTEMS; PI; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 16 Mar 2020 13:44 |
| Last Modified: | 16 Mar 2020 13:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15013 |
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