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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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Metadaten
Author:Mathias O. Senge, Katja Dahms, Hans-Jürgen Holdt, Alexandra Kelling
DOI:https://doi.org/10.1515/znb-2014-0217
ISSN:0932-0776 (print)
ISSN:1865-7117 (online)
Parent Title (English):Zeitschrift für Naturforschung : B, Chemical sciences
Publisher:De Gruyter
Place of publication:Tübingen
Document Type:Article
Language:English
Year of first Publication:2015
Year of Completion:2015
Release Date:2017/03/27
Tag:conformational analysis; crystal structure; porphyrins; tetrapyrroles
Volume:70
Issue:2
Pagenumber:5
First Page:119
Last Page:123
Funder: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