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.

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► 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.