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RESEARCH PRODUCT
Functionalization of Porphyrins: Mechanistic Insights, Conformational Studies, and Structural Characterizations
Bernard BoitrelMohammed LachkarZakaria HalimeZakaria HalimeThierry RoisnelPhilippe RichardSébastien Balieusubject
Cation bindingAtropisomer010405 organic chemistryStereochemistryOrganic Chemistry010402 general chemistry[ CHIM ] Chemical Sciences01 natural sciencesPorphyrin0104 chemical sciencesDiethyl malonatechemistry.chemical_compoundchemistryPolymer chemistry[CHIM]Chemical SciencesSurface modificationPhysical and Theoretical ChemistryComputingMilieux_MISCELLANEOUSdescription
The condensation of 3-chloromethylbenzoyl chloride with three atropisomers of meso-5,10,15,20-tetrakis(2-aminophenyl)porphyrin (TAPP) is reported, followed by the reaction of the anion of diethyl malonate to prepare various strapped porphyrins. According to two different geometries of the straps, the resulting preorganization of the hanging ethoxycarbonyl groups is more or less adapted to the coordination of cations such as lanthanides. The conformational study, as well as the X-ray structures of three strapped porphyrins, demonstrate that among the three atropisomers investigated in this work, only two of them lead to strapped porphyrins in which an ethoxycarbonyl group is directed towards the centre of the porphyrin. Additionally, we were able to explain some peculiar reactivities observed for single-strapped porphyrins, as the 5–15 strapped geometry is shown to be favoured. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-03-01 | European Journal of Organic Chemistry |