Kaletas, B. K. and Mandl, Christian and van der Zwan, G. and Fanti, M. and Zerbetto, F. and De Cola, L. and Koenig, Burkhard and Williams, R. M. (2005) Unexpected photophysical properties of symmetric indolylmaleimide derivatives. JOURNAL OF PHYSICAL CHEMISTRY A, 109 (29). pp. 6440-6449. ISSN 1089-5639,
Full text not available from this repository. (Request a copy)Abstract
Arcyriarubin A and arcyriaflavin A, two strongly emissive and intensely colored natural products containing both two indoles and a maleimide unit, are investigated (in the flavin the two indole moieties are coupled by a cyclization). The photophysical properties of these compounds were studied in several solvents using UV-vis absorption, steady-state and time-resolved emission, nano- and ferntosecond transient absorption spectroscopy. Furthermore, the effect of complexation with zinc(II) 1,4,7,11 -tetraazacyclododecane on the photophysical properties of these natural products has been investigated. The chemical structures of the compounds would suggest a charge transfer (CT) character in the ground and/or excited states, since indole is a well-known electron donor and maleimide is a good electron acceptor. Their solvatochromic behavior was investigated by using the Kamlet-Taft approach and indicates only a small CT character in the excited state. This is substantiated by the time-resolved spectroscopy and the complexation study. Molecular orbital calculations indicate that there are no electronic transitions in which a large electron density is transferred from one indole unit to the maleimide part. All calculated orbitals show a strong delocalization of the electron density over the whole molecule. These findings corroborate the experimental results. Whereas the two compounds do have a substantial (calculated) ground-state dipole moment (6 D) and show some solvatochromic behavior, they behave more like conjugated aromatic systems than like electron donor-acceptor systems.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PROTEIN-KINASE-C; SOLVATION ENERGY RELATIONSHIPS; PI-STAR; BISINDOLYLMALEIMIDES; STAUROSPORINE; RECOGNITION; INHIBITORS; PROMOTION; POTENT; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 04 May 2021 07:04 |
| Last Modified: | 04 May 2021 07:04 |
| URI: | https://pred.uni-regensburg.de/id/eprint/35867 |
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