Akademik Veri Yönetim Sistemi
Polyhedron, cilt.296, 2026 (SCI-Expanded, Scopus)
Although some studies compare oxygen and sulfur azaphthalocyanine analogues and investigate the effect of intramolecular charge transfer (ICT) on fluorescence quenching, a comprehensive understanding of this mechanism and the structure-activity relationship, particularly through the use of direct analogous pairs of oxygen and sulfur substituents, has not yet been thoroughly established.Therefore, four distinct azaphthalonitrile (1–4) starting materials derived from 3-methoxyphenol and 3-methoxythiophenol were synthesized. From these precursors, four new azaphthalocyanine compounds (1a-4a) incorporating Zn(II) ion were obtained. The newly synthesized aryl-ether and aryl-thio substituted azaphthalonitrile and azaphthalocyanine compounds were rigorously characterized using various spectroscopic methods, including FT-IR, UV/Vis, and NMR. The fluorescence emission properties of the zinc-centered azaphthalocyanines (1a-4a) were systematically examined, and their Stokes shift values and fluorescence quantum yields were calculated to detail their chemical structure-fluorescence relationships.The results demonstrate that oxo-bridged Zn-azaphthalocyanines (1a and 3a) exhibit significantly high fluorescence efficiency. In contrast, their thio-substituted analogues displayed notably lower quantum yields. This work provides new insights into the structure-property relationships of aryl-ether and aryl-thio substituted azaphthalocyanines, clearly elucidating how peripheral modifications profoundly influence their photophysical characteristics. This study offers an original and valuable contribution to the field of azaphthalocyanine chemistry, establishing a foundational framework for both academic and applied research in fluorescence-active macrocyclic systems.