A series of near-infrared (NIR) organic absorbers, named FNs and FPs, have been obtained with absorption maxima from 870 nm to 1100 nm and thus falling into the attractive second near-infrared region (NIR-II). The synthesis of their extended aromatic cores utilized an initial aryl-amination between 4-aminonaphthalene-1,8-dicarboximide (NMI-NH2 ) or 9-aminoperylene-3,4-dicarboximide (PMI-NH2 ) with chloro-substituted 9,10-anthraquinones followed by a novel base-induced cyclodehydrogenation. A NIR-II pigment, compound FPP, was obtained through de-alkylation of a soluble precursor. The synthesis of this photostable pigment is high-yielding and avoids column chromatographic purification which is important for many applications.
Keywords: cyclodehydrogenation; photostability; pigment; rylenecarboximide; second near-infrared.
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