Synthesis and Structure of meso-Substituted Dibenzihomoporphyrins.

Autor: Grover, Nitika, Emandi, Ganapathi, Twamley, Brendan, Khurana, Bhavya, Sol, Vincent, Senge, Mathias O.
Předmět:
Zdroj: European Journal of Organic Chemistry; 11/8/2020, Vol. 2020 Issue 41, p6489-6496, 8p
Abstrakt: 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 nonaromatic characteristics of the compounds synthesized. Additionally, the dibenzihomoporphyrins were found to generate singlet oxygen, potentially allowing their use as photosensitizers. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index