{"title":"Novel phthalocyanines bearing 4-(2-isopropylphenoxy) groups: Synthesis, characterization, electrochemical and in-situ spectroelectrochemical properties","authors":"","doi":"10.1016/j.jorganchem.2024.123272","DOIUrl":null,"url":null,"abstract":"<div><p>In this study, 4-(2-isopropylphenoxy)phthalonitrile (<strong>3</strong>) was prepared via a substitution reaction between 2-isopropylphenol (<strong>1</strong>) and 4-nitrophthalonitrile (<strong>2</strong>). Then, peripherally tetra 2-isopropylphenoxy substituted zinc(II) (<strong>4</strong>) and cobalt(II) (<strong>5</strong>) phthalocyanines were obtained via a cyclotetramerization reaction between phthalonitrile (<strong>3</strong>) and related metal salt. The structural characterization of synthesized compounds were completed via FT-IR, <sup>1</sup>HNMR , UV–Vis and MALDI-TOF mass data. Electrochemical and spectroelectrochemical measurements were performed to determine the potential of novel phthalocyanines to be used in electrochemical applications. While the cobalt(II) phthalocyanine (<strong>5</strong>) displayed one metal-based reduction, two ring-based reductions and one metal and ring-based oxidation; zinc(II) phthalocyanine (<strong>4</strong>) showed three ring-based reductions and one ring-based oxidation reaction. In addition, it was determined that electron-releasing isopropyl phenoxy group affected half-wave peak potentials of complexes and the Q band positions. Diffusion-controlled, reversible and multi-electron transfer abilities of the zinc(II) (<strong>4</strong>) and cobalt(II) (<strong>5</strong>) phthalocyanines showed that they have redox richness for can be used in optical technological applications.</p></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organometallic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022328X24002675","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
In this study, 4-(2-isopropylphenoxy)phthalonitrile (3) was prepared via a substitution reaction between 2-isopropylphenol (1) and 4-nitrophthalonitrile (2). Then, peripherally tetra 2-isopropylphenoxy substituted zinc(II) (4) and cobalt(II) (5) phthalocyanines were obtained via a cyclotetramerization reaction between phthalonitrile (3) and related metal salt. The structural characterization of synthesized compounds were completed via FT-IR, 1HNMR , UV–Vis and MALDI-TOF mass data. Electrochemical and spectroelectrochemical measurements were performed to determine the potential of novel phthalocyanines to be used in electrochemical applications. While the cobalt(II) phthalocyanine (5) displayed one metal-based reduction, two ring-based reductions and one metal and ring-based oxidation; zinc(II) phthalocyanine (4) showed three ring-based reductions and one ring-based oxidation reaction. In addition, it was determined that electron-releasing isopropyl phenoxy group affected half-wave peak potentials of complexes and the Q band positions. Diffusion-controlled, reversible and multi-electron transfer abilities of the zinc(II) (4) and cobalt(II) (5) phthalocyanines showed that they have redox richness for can be used in optical technological applications.
期刊介绍:
The Journal of Organometallic Chemistry targets original papers dealing with theoretical aspects, structural chemistry, synthesis, physical and chemical properties (including reaction mechanisms), and practical applications of organometallic compounds.
Organometallic compounds are defined as compounds that contain metal - carbon bonds. The term metal includes all alkali and alkaline earth metals, all transition metals and the lanthanides and actinides in the Periodic Table. Metalloids including the elements in Group 13 and the heavier members of the Groups 14 - 16 are also included. The term chemistry includes syntheses, characterizations and reaction chemistry of all such compounds. Research reports based on use of organometallic complexes in bioorganometallic chemistry, medicine, material sciences, homogeneous catalysis and energy conversion are also welcome.
The scope of the journal has been enlarged to encompass important research on organometallic complexes in bioorganometallic chemistry and material sciences, and of heavier main group elements in organometallic chemistry. The journal also publishes review articles, short communications and notes.