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Chemicals from Aromatic Hydrocarbons
Published in James G. Speight, Handbook of Petrochemical Processes, 2019
Phthalonitrile is the precursor to phthalocyanine pigments which are produced by the reaction of phthalonitrile with various metal precursors. The reaction is carried out in a solvent at around 180°C (355°F).
Metallo-phthalocyanines containing triazole substituents: Synthesis, spectroscopic and photophysicochemical properties
Published in Journal of Coordination Chemistry, 2022
Ümit Demirbaş, Dilek Öztürk, Hakkı Türker Akçay, Mahmut Durmuş, Emre Menteşe, Halit Kantekin
Compound 3 was prepared in dry DMF at 50 °C for 3 days by reaction between 5-benzyl-4-methyl-4H-1,2,4-triazole-3-thiol and 4-nitrophthalonitrile [21]. Metallo-phthalocyanines 4–6 were prepared in n-pentanol by reaction between phthalonitrile 3 and metal salt for 24 h at 160 °C. In the recorded IR spectra of phthalocyanines 4–6 the nitrile signals of phthalonitrile 3 disappeared. This change indicated that the complexation was completed. When the 1H-NMR spectra of 4–6 were examined, the aromatic and aliphatic proton signals were within the expected chemical shift and integral values. In the UV-Vis spectra of 4–6, the Q and B bands which are characteristic for metallo-phthalocyanines are further evidence of the complexation. The [M + H]+ peaks recorded in the mass spectra also supported the structures of 4–6. The obtained data are in agreement with the structural characterization of previously prepared phthalocyanines [22, 23] (Scheme 1).
Synthesis, photophysical, photochemical, and DFT properties of a zinc phthalocyanine with 2-(2-isopropyl-5-methylphenoxy)phenoxy peripheral groups
Published in Journal of Coordination Chemistry, 2022
Derya Güngördü Solğun, Ümit Yildiko, Mehmet Salih Ağirtaş
In this study, one phthalonitrile derivative and a zinc phthalocyanine complex were synthesized. The structures of the new compounds were characterized by UV–Vis, FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. The photophysical and chemical properties of the zinc phthalocyanine complex were investigated. The data zinc phthalocyanine compound was evaluated as a photosensitizer. Value ΦΔ of zinc phthalocyanine 4 was 0.61. Quantum analyses of the phthalocyanine compound were performed in the gas phase with B3PW91/6-31 G and B3LYP/LanL2DZ basis set via the DFT approach. The obtained results show that the estimated gap energy (ΔE) for molecule 4 at the level of B3PW91/6-31G and B3LYP/LanL2DZ of DFT varies between 2.21 and 2.14 eV, respectively. These low values indicate that this molecule has a high degree of conjugation. Zinc phthalocyanine reactivity properties were evaluated with the DFT approach, taking into account the energy band gap and also some global descriptors. The phthalocyanine structure has a narrower HOMO–LUMO energy range, higher global softness, electrophilicity index values and can be said to exhibit a better electrophilic profile. In addition to these, electrophilic and nucleophilic activity regions of the molecule were shown with the MEP maps in the Zn-Pc structure. The molecule has good stability of the phthalocyanine core with, for example, N6-C23 and C1-N5 π → π* transition E(2) energy 37.33 kcal mol−1. Zn-Pc molecule with NLO material properties could be useful for sensing optical signals and imaging applications with multi-photon absorption.
Computational DFT calculations, photovoltaic properties and synthesis of (2R, 3S)-2, 3, 4-trihydroxybutoxy substituted phthalocyanines
Published in Inorganic and Nano-Metal Chemistry, 2020
Beyza Cabir, Umit Yildiko, Mehmet Salih Ağırtaş, Sabit Horoz
In the IR spectrum of phthalonitrile 3, the presence of C≡N and C=C groups is indicated by the intense bands at 2231 and 1597 cm−1. The phthalocyanine compounds, unlike the starting material, do not give nitrile peaks. It confirms the structure of phthalocyanine compounds and shows that there is no starting material as impurity. Figure 1 shows the IR spectra of metallic phthalocyanine compounds and starting material phthalonitrile. 1H-NMR spectrum of phthalonitrile 3 exhibited the aromatic protons around 8.03–7.40 (Ar–H) ppm. The aliphatic protons adjacent to the hydroxyl group appeared at around 4.29–3.70 (OH) ppm, aliphatic protons 5.88–5.35(CH2) and 5.09–4.56 (CH) ppm. The 13C NMR spectrum of phthalonitrile 3 indicated the nitrile carbons at 116.67 and 116.20 ppm as expected. Aromatic carbon atoms appeared in the range at 136.19–106.24 ppm. Aromatic carbon oxygen was observed at the 162.73 ppm. 1H NMR measurements of compounds 4 and 5 were excluded due to their paramagnetic property. There is a lot of literature on the absence of NMR spectra of such cobalt and copper metal phthalocyanine compounds.[26] As a general rule, 1H NMR spectra of metal-free phthalocyanine and the phthalocyanines with diamagnetic metal ion in the core are consistent with proposed structures.[27]