meso-Ester Corroles

Chemistry : a European Journal
Gabriel CanardTeodor Silviu Balaban

Abstract

The introduction of ester groups on the 5- and 15-meso positions of corroles stabilizes them against oxidation and induces a redshift of their absorption and emission spectra. These effects are studied through the photophysical and electrochemical characterization of up to 16 different 5,15-diester corroles, in which the third meso position is free or occupied by an aryl group, a long alkyl chain, or an ester moiety. Single-crystal X-ray structure analysis of five 5,15-diestercorroles and DFT and time-dependent DFT calculations show that the strong electron-withdrawing character of the 5,15 ester substituents is reinforced by their π overlap with the macrocyclic aromatic system. The crystal packing of corroles 2, 4, 6, 9, and 15 features short distances between chromophores that are stacked into columns thanks to the low steric hindrance of meso-ester groups. This close packing is partially due to intermolecular interactions that involve inner hydrogen and nitrogen atoms, and thereby, stabilize a single, identical corrole tautomeric form.

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Citations

Oct 16, 2015·Inorganic Chemistry·Giuseppe PomaricoRoberto Paolesse
Nov 5, 2016·Chemical Reviews·Rafał OrłowskiDaniel T Gryko
Dec 24, 2016·Chemical Reviews·Yuanyuan FangKarl M Kadish
May 18, 2017·Chemistry : a European Journal·Rafał OrłowskiDaniel T Gryko
Jul 14, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Zhao ZhangHai-Yang Liu
Apr 17, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jyoti RaiJeyaraman Sankar
Mar 31, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Lucia Flamigni
Nov 15, 2017·Angewandte Chemie·Qiu-Cheng ChenZeev Gross
Apr 6, 2021·Angewandte Chemie·Pinky YadavZeev Gross
Jun 18, 2015·Organic Letters·Irena SaltsmanZeev Gross

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