Purple subphthalocyanine-phthalocyanine dyad: Synthesis, photophysicochemical properties and DFT study

Saad Makhseed, Basma Ghazal, Mahmut Durmuş

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A new phthalocyanine-subphthalocyanine heterodyad (5) was prepared by Pd(0)-catalyzed Sonogashira coupling reaction between an asymmetrical phthalocyanine (3) bearing monoiodo and multiple triazolide moieties on its backbone and a subphthalocyanine (4) bearing axially propargyl group. The structure of this heterodyad (5) was subsequently confirmed by the conventional spectroscopic techniques. The photophysical and photochemical properties including; fluorescence and singlet oxygen generation of (5) along with its building chromophores (3) and (4) were also investigated. Interestingly, a purple colored solution was observed by this novel dyad which was significantly different from those colors (green or blue) obtained by phthalocyanine-subphthalocyanine conjugates. Based on steady state absorption spectroscopic data and transient absorption results, the synthesized dyad 5 was free of aggregation and there is good energy transfer occurs between Pc and subPc moieties. This result was confirmed using density functional theory (DFT) and time-dependent DFT (TDDFT) analyses: B3LYP exchange-correlation functional and the 6–31 + G(d) basis set.

Original languageEnglish
Article numbere5780
JournalApplied Organometallic Chemistry
Volume34
Issue number9
DOIs
StatePublished - 1 Sep 2020

Keywords

  • DFT Study
  • energy transfer
  • heterodyad
  • phthalocyanine
  • subphthalocyanine

Funding Agency

  • Kuwait Foundation for the Advancement of Sciences

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