3 research outputs found
Photoacoustic Technique Applied to Skin Research: Characterization of Tissue, Topically Applied Products and Transdermal Drug Delivery
<i>meso</i>‑Tetraphenylbenzoporphyrin‑2<sup>2</sup>,2<sup>3</sup>‑dicarboxylic Anhydride: A Platform to Benzoporphyrin Derivatives
A method
to synthesize <i>meso</i>-tetraphenylbenzoporphyrin-2<sup>2</sup>,2<sup>3</sup>-dicarboxylic anhydride is reported. This compound
reacts with alkylamines and arylamines to afford the corresponding
“phthalimides” in moderate to excellent yields. The
reaction of the title compound with benzene-1,4-diamine or with benzene-1,3-diamine
yields the corresponding <i>N</i>,<i>N</i>′-(phenylene)bisphthalimides,
whereas with benzene-1,2-diamine or naphthalene-1,8-diamine it affords
heterocyclic-fused porphyrins. Molecular mechanics simulations elucidates
the multiplicity of signals observed in the NMR spectra of the <i>N</i>,<i>N</i>′-(1,4-phenylene)bisphthalimide <b>11</b>. This molecule exhibits two preferential conformations
corresponding to a coplanar and an almost perpendicular arrangement
of the benzoporphyrin units relative to the central benzenic ring