A Heck-type coupling for the synthesis of novel bridged metallochlorin-fullerene C-60 dyads
- A short and convenient synthesis of metallochlorin-C-60 dyads based on a Heck-type hetero coupling at the 3(2) position of a chlorin is described. p-Bromobenzaldehyde was treated with Zn-metalated 13(2)- demethoxycarbonylmethylpheophorbide a, using a palladium acetate/LiCl catalyst mixture under phase-transfer conditions in DMF at 70 degrees C. The resulting asymmetric olefin was obtained in a high trans/cis ratio. The desired trans isomer was separated and subsequently transformed into a donor-acceptor dyad by a 1,3-dipolar cycloaddition to C-60 in the presence of sarcosine in refluxing toluene. The resulting dyads are expected to undergo efficient photoinduced electron transfer and can potentially be utilized in solar energy conversion devices.
| Author details: | Martin Katterle, Alfred R. Holzwarth, Aldo Jesorka |
|---|---|
| URL: | http://www3.interscience.wiley.com/cgi-bin/jhome/27380/ |
| DOI: | https://doi.org/10.1002/ejoc.200500494 |
| ISSN: | 1434-193X |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2006 |
| Publication year: | 2006 |
| Release date: | 2017/03/24 |
| Source: | European journal of organic chemistry. - ISSN 1434-193X. - 16 (2006), 2, S. 414 - 422 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
| Institution name at the time of the publication: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Organische Chemie und Strukturanalytik |
