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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.

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Author details:Mathias O. Senge, Katja Dahms, Hans-Jürgen HoldtORCiD, Alexandra Kelling
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
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