Bimberg, Ben C. and Blaser, Florian K. and Pidenko, Pavel S. and Ramos, Javier Recio and Fedotova, Elena and Mueller, Bastian and Burmistrova, Natalia A. and Baeumner, Antje J. and Duerkop, Axel and von Wangelin, Axel Jacobi (2025) Fluorescent and Chemiluminescent Dyes with Aryl Phthalimide and Aryl Luminol Chromophores. CHEMPHOTOCHEM, 9 (8): e202500064. ISSN 2367-0932,
Full text not available from this repository. (Request a copy)Abstract
Luminol is one of the most widely established and most well-known chemiluminescent molecules with diverse applications in modern analytical sciences such as forensics and cell assays. Structural and electronic modifications of the parent luminol can effectively enhance the (photo)physical and (photo)chemical properties. Herein, a straightforward route to stereoelectronically modulated luminol derivatives is developed by utilization of an effective cross-coupling at a versatile bromo phthalimide precursor. The modular synthesis enabled convenient access to two distinct classes of photoactive molecules: highly fluorescent 6-aryl-4-amino N-methyl phthalimides and chemiluminescent 7-aryl luminol derivatives. Electron-rich aryl substituents are shown to significantly enhance chemiluminescence (CL) quantum yields and exhibit good limits of detection in a CL hydrogen peroxide assay. The stereoelectronic effects on absorption, fluorescence, and CL properties are evaluated by experimental and theoretical studies.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | RESONANCE ENERGY-TRANSFER; HYDROGEN-PEROXIDE; ELECTROGENERATED CHEMILUMINESCENCE; QUANTUM-DOTS; DERIVATIVES; ELECTROCHEMILUMINESCENCE; MECHANISM; ANALOGS; SYSTEM; PROBE; biaryl cross-coupling; chemiluminescence; fluorescent dyes; luminol; structure-activity relationships |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Analytische Chemie, Chemo- und Biosensorik > Chemo- und Biosensorik (Prof. Antje J. Bäumner, formerly Prof. Wolfbeis) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 07 May 2026 05:11 |
| Last Modified: | 07 May 2026 05:11 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66849 |
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