Porphyrin substituent regiochemistry, conformation and packing - the case of 5,10-diphenylporphyrin
- 5,10-Disubstituted porphyrins are more recent additions to the family of meso-substituted porphyrins. A crystallographic comparison of 5,10-diphenylporphyrin with the regioisomeric 5,15-disubstituted system reveals striking differences in their conformation. In the free base porphyrins the former uses mainly out-of-plane distortion to alleviate steric strain while in-plane core elongation predominates in the latter. In contrast, the structure of the Cu(II) complex is planar and forms strong p-p aggregates with very small lateral shifts. Macroscopically, the packing is similar to that of porphyrin sponges of the 5,10,15,20-tetraphenylporphyrin type.
Author details: | Mathias O. Senge, Katja Dahms, Hans-Jürgen HoldtORCiD, Alexandra Kelling |
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DOI: | https://doi.org/10.1515/znb-2014-0217 |
ISSN: | 0932-0776 |
ISSN: | 1865-7117 |
Title of parent work (English): | Zeitschrift für Naturforschung : B, Chemical sciences |
Publisher: | De Gruyter |
Place of publishing: | Tübingen |
Publication type: | Article |
Language: | English |
Year of first publication: | 2015 |
Publication year: | 2015 |
Release date: | 2017/03/27 |
Tag: | conformational analysis; crystal structure; porphyrins; tetrapyrroles |
Volume: | 70 |
Issue: | 2 |
Number of pages: | 5 |
First page: | 119 |
Last Page: | 123 |
Funding institution: | Science Foundation Ireland [SFI P.I. 09/IN.1/B2650, IvP 13/IA/1894 SFI] |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Peer review: | Referiert |