Noell, Gilbert and Daub, Joerg and Lutz, Michaela and Rurack, Knut (2011) Synthesis, Spectroscopic Properties, and Electropolymerization of Azulene Dyads. JOURNAL OF ORGANIC CHEMISTRY, 76 (12). pp. 4859-4873. ISSN 0022-3263,
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Four azulene dyads have been synthesized and studied by spectroscopic and electrochemical methods. A triarylamine, a boron-dipyrromethene (BDP or BODIPY), a porphyrin, and an isoalloxazine moiety have been linked to an extended pi electron system at the 2-position of azulene, leading to the dyads 1-4, respectively. For the synthesis of 1-4, first 2-(4-ethynyl-phenyl)azulene (EPA) was prepared, which was further reacted with the halogenated chromophores by Pd-catalyzed cross-coupling reactions. The dyads 1-4 exhibit strong absorption bands in the visible range, which are dominated by the absorption spectra of the individual subchromophores. Fluorometric studies of 2-4 revealed that after excitation of the subchromophoric unit attached to the parent azulene moiety, quenching mainly through energy,. transfer to azulene is effective, whereas possible charge-transfer interactions play only a minor role. Potentiodynamic oxidation of the dyads 1-4 leads to the formation of polymer films, which are deposited at the electrode. The polymer film derived from 1 was further characterized by spectroelectrochemistry. During positive doping of poly-1, a strong absorption band appears at 13,200 cm(-1), which is typical for triarylamine radical cations. This band is overlapping with a broad absorption band in the low-energy region that might be caused by charge-transfer interactions within the polymer.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HETEROJUNCTION SOLAR-CELLS; INVERSE RING POLARIZATION; SELF-ASSEMBLED MONOLAYERS; OPEN-CIRCUIT VOLTAGE; CHARGE-TRANSFER; ENERGY-TRANSFER; CONDUCTING POLYMERS; ELECTRON-TRANSFER; HIGHLY EFFICIENT; PHOTOELECTROCHEMICAL PROPERTIES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Prof. Dr. Jörg Daub |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 09 Jun 2020 08:44 |
| Last Modified: | 09 Jun 2020 08:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/20654 |
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