Synthesis of model bacteriochlorophylls containing substituents of native rings A, C and E

Abstract

An established route to the bacteriochlorophyll skeleton from two dihydrodipyrrin halves has been extended to accommodate several substituents characteristic of the native bacteriochlorophyll a.

Design and Characterisation of pH-Responsive Photosensitiser-Loaded Nano-Transfersomes for Enhanced Photodynamic Therapy

“…The FTIR spectra of F1 and F2 demonstrated that the peaks for both formulations were not detected for both C=C stretching and C=O stretching and shifted for N-H stretching to 3675 and 3672 cm −1 , respectively. This suggests that cholesterol is the difference in composition between F1 and F2 [40,41]. Additionally, the peak of N-H stretching in MPa was slightly shifted when comparing F1 with F2.…”

“…Additionally, the peak of N-H stretching in MPa was slightly shifted when comparing F1 with F2. Therefore, the H of N-H stretching in MPa forms a weak H-bond (hydrogen bond) with the hydroxyl group in cholesterol [40,41].…”

Synthesis of bacteriochlorins bearing diverse β-substituents

“…2). While 1 H NMR spectroscopic analysis routinely affords a characteristic ABX pattern of the methylene protons on the carbon adjacent to the stereogenic center, structural analysis of such pyrrole–nitrohexanones has previously been reported for only four compounds, 46–48 although compounds containing the 2-(2-nitroethyl)pyrrole moiety are growing in importance. 49…”

“…2). While 1 H NMR spectroscopic analysis routinely affords a characteristic ABX pattern of the methylene protons on the carbon adjacent to the stereogenic center, structural analysis of such pyrrole-nitrohexanones has previously been reported for only four compounds, [46][47][48] although compounds containing the 2-(2-nitroethyl)pyrrole moiety are growing in importance. 49 To our surprise, the standard self-condensation conditions 15 afforded 5-unsubstituted BC-1 only in 4.1% yield and was accompanied by 5-methoxybacteriochlorin BC-2 in 1.7% yield.…”

Chlorophylls: A Personal Snapshot

“…Their stereochemistry was determined by Ian Fleming, by Burrell et al and by Crabbé et al (reviewed in Brockmann, [ 16 ]). Total syntheses were achieved by the groups of Strell [ 17 ] and, more rigorously, Woodward [ 18 ], but a general synthetic access of Chl-type pigments remains a challenge [ 19 , 20 ].…”