A3B and ABAB aminophthalocyanines: Building blocks for dimeric and polymeric constructs

BOZKURT EKREN S., DUMOULİN F., Musluoglu E., AHSEN V., GÜNGÖR Ö.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.23, pp.1448-1454, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23
  • Publication Date: 2019
  • Doi Number: 10.1142/s1088424619501499
  • Journal Name: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1448-1454
  • Keywords: asymmetric phthalocyanine, dimer, polymer, PHOTOPHYSICAL PROPERTIES, TIN(IV) PHTHALOCYANINES, LIQUID-CRYSTALS, METAL-COMPLEXES, SUBSTITUTION, INACTIVATION, INDIUM(III), DERIVATIVES, SENSITIZERS, COPPER(II)
  • Kocaeli University Affiliated: Yes

Abstract

Mono or diamino phthalocyanines with A3B or crosswise ABAB substitution patterns have been synthesized and used as building blocks for the preparation of dimeric and polymeric phthalocyanines. For this, 4,5-di(dodecylsulfanyl) phthalonitrile was converted into 1 ,3-diimino-6,7-di-(n-dodecylsulfanyl)-isoiminoindoline and then reacted with 6-nitro-1,3,3-trichloroisoindoline. The nitro functions on the resulting inseparable mixture of A3B and ABAB phthalocyanines were reduced into amines by Na2S and the phthalocyanines could be chromatographically separated. Dimeric phthalocyanine was synthesized by the reaction of the mono-amino AB3 with sebacoyldichloride, and a poorly soluble linear polymeric material was obtained by reaction of the ABAB di-amino phthalocyanine with sebacoyl dichloride.