Tailored Synthesis of N-Substituted peri-Xanthenoxanthene Diimide (PXXDI) and Monoimide (PXXMI) Scaffolds

Abstract

The tailored synthesis of homo (A2) and hetero (AB) N-substituted peri-xanthenoxanthene diimides (PXXDIs) and peri-functionalized PXX monoimides (PXXMIs) from 3-hydroxy naphthalic anhydride is described. As A2-type PXXDIs could be synthesized in one step, AB-type PXXDIs and PXXMIs were prepared through a modular approach capitalizing on sequential Suzuki coupling, Imidation and Pummerer reactions with very high yields. In view of their potential applications as organic semiconductors, self-organization studies were performed through liquid deposition on surfaces, depicting the formation of islands, needles and rods.

Synthesis and Photodynamic Activity of <i>Peri</i>-xanthenoxanthene Derivatives

“…The synthetic route is outlined in Chart 1. Substituted 2-naphthol underwent self-coupling or cross-coupling reactions to obtain the target products via solid-phase carbon-bath microwave method 15) in the presence of copper acetate. The reaction was fast and took only 6 to 12 min.…”

“…But the maximum absorption wavelength of PXX can reach more than 600 nm after structural modification. 16) So PXX still has application prospects.…”

“…With good charge transfer properties, thermal stability, and chemical stability, these compounds are often used as compositions of pigments, charge transfer complexes, and organic semiconductors in electronic devices. [9][10][11][12][13][14][15] To the best of our knowledge, PXX derivatives have never been used in anti-tumor applications.…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…To further investigate the synthetic methods toward the peri -xanthenoxanthene diimide 135.4a , a direct oxidative Pummerer dimerization was examined ( Scheme 135 ). 272 The homocoupling of 135.5 was done in up to 43% yield in the presence of CuCl in DMSO under air. An alternative pathway toward 135.4a and related compounds was also described in the same study.…”

Oxygen‐Doped PAH Electrochromes: Difurano, Dipyrano, and Furano‐Pyrano Containing Naphthalene‐Cored Molecules

“…[79,80] Recently, our group has gone on to expand the library of Odoped PAHs through the development of Cu-catalysed intramolecular etherification reactions. [81][82][83][84][85][86] For instance, we have demonstrated that smaller O-doped molecules containing furanyl, pyranyl, and oxepinyl moieties could be easily accessed through CuO-mediated Pummerer-type oxidative cyclisation. [87] In these works, it has been shown that the formation of pyrano rings provokes a rise of the HOMO energy level, which results in a shrinking of the HOMO-LUMO gap and in the lowering of the oxidation potential.…”