102040-65-3Relevant academic research and scientific papers
Studies on the Conformation of 5,15-Diarylporphyrins with (Arylsulfonyl)oxy Substituents
Sanders, Georgine M.,Dijk, Marinus van,Veldhuizen, Albertus van,Plas, Henk C. van der,Hofstra, Ulbert,Schaafsma, Tjeerd J.
, p. 5272 - 5281 (2007/10/02)
Dimeso-substituted octaalkylporphyrins, carrying an (arylsulfonyl)oxy group at the ortho position of the two (meso) phenyl groups, were synthesized from dipyrrolylmethanes and aldehydes.On account of a 1H NMR upfield shift in CDCl3 solution of 2-5 ppm for the aryl protons, a folded conformation is assumed in which the substituted aryl groups lie right above and below the porphyrin plane.In CDCl3/CF3COOH solution the upfield shifts are absent.The results of low-temperature 1H NMR measurements and ring-current calculations agreed with our assumptions.The sulfonyloxy group promotes folding of the molecule more than the ester, sulfonyl, sulfinyl, thio, or methylene group.In zinc porphyrins carrying anthraquinone substituents, intramolecular coordination was observed. ΔG, ΔH, and ΔS values for the various conformational equilibria were calculated from the NMR data.We suggest van der Waals interactions with a contribution of charge transfer as the driving force for the folding of the molecule.
SYNTHESIS AND FOLDED CONFORMATION OF SOME 5,15-DIARYLOCTAMETHYLPORPHYRINS WITH A SULFONYLOXY GROUP IN THE ARYL PART
Sanders, G. M.,Dijk, M. van,Koning, G. P.,Veldhuizen, A. van,Plas, H. C. van der
, p. 243 - 244 (2007/10/02)
The porphyrins 1a-g were synthesized.In CDCl3 solutions 1a and 1b occur to an important extent in a folded conformation, as is indicated by an upfield shift of 2 -3 ppm for the tosylprotons in the 1H NMR spectrum.For compounds with longer chains or an est
