Synthesis of 2,3,11,12,20,21,29,30‐octadodecylthio‐2,3‐naphthalocyanines

Abstract

The title compounds were synthesized. They were soluble in organic solvents and their Q bands showed bathochromic shifts compared with unsubstituted 2,3‐naphthalocyanines.

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“…Predictably, the equivalent naphthalocyanine derivative 6(R~alkyl; M~Zn 2z ) has a clearing point above its decomposition temperature (w300 uC). 24,25 The largest macrodiscotic compound based on a Pc-type structure, reported to date, is the tetrapyrazinoporphyrazine 7(R~C 12 H 25 ) described by Ohta et al that has a rigid core of diameter y2.4 nm. 26 This material displays a columnar mesophase which is stable over the entire accessible temperature range (v2100 to w300 uC).…”

Reactions of Benzyne−Nickel(0) Complexes with Thioalkynes: Preparation and Coordination of Polydentate Thioethers Containing a 2,3-Naphthylene Backbone

“…The preparation of naphthalenes selectively substituted in the 2 and 3 positions by reactive groups for use as chelating ligands is notoriously difficult, and in this context, few preparations of such compounds bearing thiol , or thioether groups − have been reported. Some naphthalene-2,3-dithiolato complexes have been prepared with tungsten(VI) as models for oxidoreductases 32 or with gold(III) for the study of their luminescent properties, but to the best of our knowledge, no coordinated thioether analogue has been reported and complex 6 represents the first example.…”

Phthalocyanines and Naphthalocyanines with Sulfur-Containing Functional Groups: Synthesis, Preparation of Hybrid Gold Nanoparticles and Some Application Areas

“…[14] Previously, only one approach to the synthesis of 2,3-dicyanonaphthalenes substituted with functional groups containing sulfur was described in the literature. [54][55][56][57] Bromo-substituted 2,3-dicyanonaphthalenes 8, which are obtained starting from bis(dibromomethyl)benzenes, are used as the initial compound. [14,58] These tetrabromides under the action of sodium iodide are converted into o-quinodimethanes 8´, which enter into the Diels-Alder reaction with fumaronitrile.…”

“…Alkylthio-and arylthio-substituted 2,3-dicyanonaphthalenes 9 obtained from compounds 8a,b are presented in Table 5. Copper salts of alkylthiols, [54,55,57] or thiolate obtained by the action of 1,8-diazabicyclo[5.4.0]undecene-7 (DBU) [56] were used in the synthesis (Table 5). Copper salts of alkyl thiols can be formed in situ or can be prepared and isolated in advance.…”

“…The authors of [55,56] carried out the synthesis of naphthalocyanine complexes under milder conditions (Scheme 22, Table 8): boiling 1-pentanol or 1-hexanol. Both the diiminoisoindoline derivative (1) and the corresponding nitrile (2) were used as starting compounds.…”