ChemInform Abstract: Octaalkoxy Phthalocyanine and Naphthalocyanine Derivatives: Dyes with Q‐Band Absorption in the Far Red or Near Infrared.

Abstract

The tetramerization of dicarbonitriles such as (I) is catalyzed by lithium alkoxides and leads to the dyes (II) and their analogues (IIIa) and (IIIb).

Chemoselective Synthesis of Aryloxy-Substituted Phthalocyanines

“…Chemical shifts are expressed in δ (ppm) values, and coupling constants are expressed in hertz (Hz). 1 H and 13 C{ 1 H} NMR spectra were referenced to the tetramethylsilane (TMS) or the residual solvent as an internal standard. The 31 P{ 1 H} NMR spectrum was referenced to 85% H 3 PO 4 solution (0.0 ppm).…”

“…3-Hydroxypyridine was also used in this reaction, and pyridyloxy groups could be introduced (1e). All phthalonitriles were characterized by 1 H and 13 C NMR spectroscopy as well as HR-ESI-FT-ICR mass spectroscopy. The solid-state structure of 1a was also determined (Figure S1).…”

“…In the case of alkyloxy-substituted phthalonitriles, alkoxide exchange proceeds only for 4,5-dichloro-substituted phthalonitriles or 3,8-substituted naphthalonitriles. 13 However, the exchange reaction of aryloxy-substituted phthalonitriles proceeds smoothly due to the lower basicity of the aryloxy anions. The lead-mediated route was also effective for such phthalonitriles.…”