Adam, Waldemar and Nikolaus, Achim and Sauer, Juergen (1999) Influence of bridgehead substitution and ring annelation on the photophysical properties of polycyclic DBO-type azoalkanes. JOURNAL OF ORGANIC CHEMISTRY, 64 (10). pp. 3695-3698. ISSN 0022-3263,
Full text not available from this repository. (Request a copy)Abstract
The photophysical data for the polycyclic, bridgehead-substituted derivatives 1-10 of the photo-reluctant diazabicyclo[2.2.2]oct-2-ene (DBO) are presented. Substitution on the bridgehead positions with radical-stabilizing substituents enhances the photoreactivity (Phi(r)) and decreases the fluorescence quantum yields (Phi(f)) and lifetimes (tau) compared to the parent DBO. The annelated rings have no influence on the photoreactivity, except when steric interactions with an a substituent hinder the optimal radical-stabilizing conformation. The fused rings and some of the bridgehead substituents reduce the solvent-induced quenching of the singlet-excited azo chromophore by steric shielding of the azo group and, thus, increase the fluorescence quantum yields and lifetimes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HYDROGEN ABSTRACTION; RELUCTANT AZOALKANES; 2,3-DIAZABICYCLO<2.2.2>OCT-2-ENE; RADICALS; STATES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Feb 2023 14:38 |
| Last Modified: | 14 Feb 2023 14:38 |
| URI: | https://pred.uni-regensburg.de/id/eprint/49244 |
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