Synthesis and characterization, aggregation and electrochemical redox properties of beta and octa 5-[4-(1,1,3,3-tetramethylbutyl)phenoxy]penta-n-1-ol substituted phthalocyanines
SYNTHETIC METALS, cilt.321, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 321
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.synthmet.2026.118276
- Dergi Adı: SYNTHETIC METALS
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC
- Anahtar Kelimeler: 4-tert-octyphenol, Aggregation, Electrochemistry, Phthalocyanine, Spectroelectrochemistry, Synthesis
- Karadeniz Teknik Üniversitesi Adresli: Evet
Özet
The synthesis, characterization, and aggregation properties of new phthalocyanine compounds, including 5-[4-(1,1,3,3-tetramethylbutyl)phenoxy]pentan-1-ol groups, have been reported. The metal-free compound 3 was obtained through a cyclotetramerization reaction involving 5-[4-(1,1,3,3-tetramethylbutyl)phenoxy]penty}oxy) substituted phthalonitrile compound 2. On the other hand, complexes 4-5 were synthesized by the reaction of compound 2 and complexes 7-8 were synthesized by the reaction of 4,5bis(5-[4-(1,1,3,3-tetramethylbutyl)phe-noxy]penty}oxy) substituted phthalonitrile compound 6 to obtain the corresponding dinitrile-derived complexes, the reactions were carried out using the appropriate anhydrous metal salts in n-pentanol in the presence of DBU. The molecular structures of all synthesized parent compounds were elucidated through the application of FT-IR, UV-vis spectroscopic data, 13C NMR, 1H NMR, Mass, and elemental analysis. The electrochemical redox properties of compounds 3-5 and 7-8 were investigated with voltammetric and in situ spectroelectrochemical methods. The spectral and electrochemical redox properties of compounds 3-5 and 7-suggested aggregation tendencies. Furthermore, the redox-inactive metal-centered ZnPc (4) and metal-free H2Pc (3) compounds exhibited only ring-based redox processes. In contrast, the redox-active metal-centered compounds CoPc (5), CoPc (7), and Mn(OAc)Pc (8) showed additional metal-based redox behaviors. In contrast to the other complexes, Mn(OAc)Pc (8) showed metal-based M3+/M2+ reduction and M3+/M4+ oxidation processes owing to the initial + 3 oxidation state of the manganese metal center. The distinct spectral and color changes, coupled with its rich redox behavior, highlight the potential of Mn(OAc)Pc (8) as a functional material for electrochemical and electrochromic applications.