Synthesis and photophysical studies of a chlorin sterically designed to prevent self-aggregation

Synthesis and photophysical evaluations of a new non-aggregating chlorin derivative are described. A β-octa(carboxyethyl)porphyrin 3 was synthesized in 2 steps starting from pyrrole-3,4-dicarboxylic acid diethyl ester (2). The new chlorin derivative 6 was obtained through a 1,3-dipolar cycloaddition using benzyl azomethine ylide. Chlorin 6 presents a molecular scaffold in an “L” shape avoiding aggregation in solutions at 1–27 mM. Photophysical properties were measured, and indicate that this new compound can be considered a useful candidate for PDT studies.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of a new non-aggregating chlorin derivative is described. ► A 1,3-dipolar cycloaddition was used as the key step. ► This new chlorin has proven to be a good candidate for PDT studies.