Synthesis and photophysical properties of A3B-type non-symmetrically substituted anthracene-based zinc(II) phthalocyanine

Year 2020, , 107 - 116, 15.02.2020

Sinem Temizel Altuğ Mert Sevim

https://doi.org/10.18596/jotcsa.633901

Abstract

A novel unsymmetrical zinc(II) phthalocyanine (ZnPc) (3) with an
alkynyl functional group was prepared by an efficient mixed
statistical condensation of 4-((4-ethynylbenzyl)oxy)phthalonitrile
(1) and 4-(4-tertbutylphenoxy)phthalonitrile (2). FTIR, 1H NMR,
UV-Vis, elemental analysis, and MALDI-TOF were used to characterize
this new compound. Working with different concentrations, the
compound’s aggregation properties were investigated and concluded
that no aggregation tendency has been observed in the studied
concentration range (1.0 x 10-6 M to 1.2 x10-5 M). Fluorescent
quantum yields and lifetimes of the compound were studied and found
to be 0.09 and 0.57 ns, respectively. As a fluorescent quencher,
1,4-benzoquinone was used in the experiments at differing
concentrations in tetrahydrofuran. The kq values showed a close
follow-up to the diffusion control limits, around 1011 s-1 and they
seem to agree with Einstein-Smoluchowski’s approximation for
bimolecular, diffusion-control-including, interactions. For the new
compound, the KSV value was calculated as 27.55, which is lower than
that of unsubstituted ZnPc. The fluorescence of the studied compound
3 was effectively quenched by 1,4-benzoquinone.

Keywords

Zinc, anthracene, phthalocyanine, fluorescence, characterization

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