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Synthesis and Structure of meso ‐Substituted Dibenzihomoporphyrins
Author(s) -
Grover Nitika,
Emandi Ganapathi,
Twamley Brendan,
Khurana Bhavya,
Sol Vincent,
Senge Mathias O.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001165
Subject(s) - chemistry , moiety , molecule , porphyrin , aryl , crystal structure , singlet oxygen , phenylene , condensation , ene reaction , crystallography , stereochemistry , photochemistry , oxygen , organic chemistry , alkyl , thermodynamics , polymer , physics
Bench‐stable meso‐substituted di( p/m ‐benzi)homoporphyrins were synthesized through acid‐catalyzed condensation of dipyrrole derivatives with aryl aldehydes. The insertion of a 1,1,2,2‐tetraphenylethene (TPE) or but‐2‐ene‐2,3‐diyldibenzene unit in the porphyrin framework results in the formation of dibenzihomoporphyrins, merging the features of hydrocarbons and porphyrins. Single crystal X‐ray analyses established the non‐planar structure of these molecules, with the phenylene rings out of the mean plane, as defined by the dipyrromethene moiety and the two meso‐carbon atoms. Spectroscopic and structural investigations show that the macrocycles exhibit characteristics of both TPE or but‐2‐ene‐2,3‐diyldibenzene and dipyrromethene units indicating the non‐aromatic characteristics of the compounds synthesized. Additionally, the dibenzihomoporphyrins were found to generate singlet oxygen, potentially allowing their use as photosensitizers.