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Synthesis and Structure of meso-Substituted Dibenzihomoporphyrins.

ABSTRACT: 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.

SUBMITTER: Grover N

PROVIDER: S-EPMC7702178 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Synthesis and Structure of meso-Substituted Dibenzihomoporphyrins.

Grover Nitika N Emandi Ganapathi G Twamley Brendan B Khurana Bhavya B Sol Vincent V Senge Mathias O MO

European journal of organic chemistry 20200928 41

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 ...[more]

PMID: 33328793

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