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Phthalocyanines and Their Analogues: Something Old, Something New
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Phthalocyanines and Their Analogues: Something Old, Something New

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (30 March 2020) | Viewed by 20178

Special Issue Editor

Prof. Dr. Tamara Basova

E-Mail Website
Guest Editor
Nikolaev Institute of Inorganic Cmemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia
Interests: optical sensors; chemiresistive sensors; amperometric sensors; gas detection; phthalocyanine thin films
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Metal phthalocyanines were discovered in the early 20th century, but they still attract the attention of researchers due to their unique optical, electrochemical, catalytic, and semiconductor properties. Phthalocyanines and their analogues are widely used in various fields of science and technology. The development in recent decades of such new scientific directions as chemistry of nanostructured materials, supramolecular chemistry, molecular electronics, initiated the use of their hybrid materials with carbon nanomaterials and metal nanoparticles as active layers of various electronic devices. The main target of this Special Issue is to provide a broad survey of the application of metal phthalocyanines and their hybrid materials as dyes, chemical sensors, catalysts of chemical processes, materials for nonlinear optics, and sensitizers in photodynamic therapy of oncological diseases. Articles devoted to basic research of structure–property correlations in phthalocyanines and other porphyrin-type compounds are also welcome.

Prof. Dr. Tamara Basova
Guest Editor

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Keywords

  • Phthalocyanine dyes
  • Phthalocyanine-based hybrid materials
  • Chemiresistive chemical sensors
  • Optical sensors
  • Electrochemistry
  • Photodynamic therapy
  • Photoinduced energy- and electron-transfer materials
  • Catalysts
  • Optical limiting

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Published Papers (5 papers)

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Research

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12 pages, 2082 KiB  
Article
Chlorosubstituted Copper Phthalocyanines: Spectral Study and Structure of Thin Films
by Alexandr Sukhikh, Dmitry Bonegardt, Darya Klyamer, Pavel Krasnov and Tamara Basova
Molecules 2020, 25(7), 1620; https://doi.org/10.3390/molecules25071620 - 1 Apr 2020
Cited by 10 | Viewed by 3353
Abstract
In this work, the tetra-, octa- and hexadecachloro-substituted copper phthalocyanines CuPcClx (where x can equal 4, 8 or 16) were investigated by the methods of vibrational (IR and Raman) spectroscopy and X-ray diffraction. The assignment of the most intense bands, both in [...] Read more.
In this work, the tetra-, octa- and hexadecachloro-substituted copper phthalocyanines CuPcClx (where x can equal 4, 8 or 16) were investigated by the methods of vibrational (IR and Raman) spectroscopy and X-ray diffraction. The assignment of the most intense bands, both in IR and Raman spectra, was carried out on the basis of DFT calculations. The structure of a CuPcCl4 single crystal grown by sublimation in vacuum was refined for the first time. The effect of chloro-substitution on the structure of CuPcClx thin films deposited in a vacuum onto a glass substrate at 50 and 200 °C was studied. It was shown that CuPcCl4 formed polycrystalline films with the preferential orientation of the (100) crystallographic plane of crystallites parallel to the substrate surface when deposited on a substrate at 50 °C. Introduction of more Cl-substituents into the phthalocyanine macrocycle leads to the formation of amorphous films on the substrates at 50 °C. At the elevated substrate temperature, the growth of polycrystalline disordered films was observed for all three copper phthalocyanines. Full article
(This article belongs to the Special Issue Phthalocyanines and Their Analogues: Something Old, Something New)
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14 pages, 2909 KiB  
Article
α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties
by Hande Pekbelgin Karaoğlu and Ayfer Kalkan Burat
Molecules 2020, 25(2), 363; https://doi.org/10.3390/molecules25020363 - 16 Jan 2020
Cited by 11 | Viewed by 4305
Abstract
Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the [...] Read more.
Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained. Full article
(This article belongs to the Special Issue Phthalocyanines and Their Analogues: Something Old, Something New)
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20 pages, 3910 KiB  
Article
FePc and FePcF16 on Rutile TiO2(110) and (100): Influence of the Substrate Preparation on the Interaction Strength
by Reimer Karstens, Mathias Glaser, Axel Belser, David Balle, Małgorzata Polek, Ruslan Ovsyannikov, Erika Giangrisostomi, Thomas Chassé and Heiko Peisert
Molecules 2019, 24(24), 4579; https://doi.org/10.3390/molecules24244579 - 13 Dec 2019
Cited by 12 | Viewed by 4152
Abstract
Interface properties of iron phthalocyanine (FePc) and perfluorinated iron phthalocyanine (FePcF16) on rutile TiO2(100) and TiO2(110) surfaces were studied using X-ray photoemission spectroscopy (XPS), X-ray absorption spectroscopy (XAS), and low-energy electron diffraction (LEED). It is demonstrated that [...] Read more.
Interface properties of iron phthalocyanine (FePc) and perfluorinated iron phthalocyanine (FePcF16) on rutile TiO2(100) and TiO2(110) surfaces were studied using X-ray photoemission spectroscopy (XPS), X-ray absorption spectroscopy (XAS), and low-energy electron diffraction (LEED). It is demonstrated that the interaction strength at the interfaces is considerably affected by the detailed preparation procedure. Weak interactions were observed for all studied interfaces between FePc or FePcF16 and rutile, as long as the substrate was exposed to oxygen during the annealing steps of the preparation procedure. The absence of oxygen in the last annealing step only had almost no influence on interface properties. In contrast, repeated substrate cleaning cycles performed in the absence of oxygen resulted in a more reactive, defect-rich substrate surface. On such reactive surfaces, stronger interactions were observed, including the cleavage of some C–F bonds of FePcF16. Full article
(This article belongs to the Special Issue Phthalocyanines and Their Analogues: Something Old, Something New)
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13 pages, 3160 KiB  
Article
Nanomaterials Based on Fe3O4 and Phthalocyanines Derived from Cashew Nut Shell Liquid
by Viviane G. P. Ribeiro, João P. F. Mota, Antônio E. Costa Júnior, Nayane M. A. Lima, Pierre B. A. Fechine, Juliano C. Denardin, Luigi Carbone, Ermelinda Bloise, Giuseppe Mele and Selma E. Mazzetto
Molecules 2019, 24(18), 3284; https://doi.org/10.3390/molecules24183284 - 9 Sep 2019
Cited by 11 | Viewed by 3007
Abstract
In this work we report the synthesis of new hybrid nanomaterials in the core/shell/shell morphology, consisting of a magnetite core (Fe3O4) and two consecutive layers of oleic acid (OA) and phthalocyanine molecules, the latter derived from cashew nut shell [...] Read more.
In this work we report the synthesis of new hybrid nanomaterials in the core/shell/shell morphology, consisting of a magnetite core (Fe3O4) and two consecutive layers of oleic acid (OA) and phthalocyanine molecules, the latter derived from cashew nut shell liquid (CNSL). The synthesis of Fe3O4 nanoparticle was performed via co-precipitation procedure, followed by the nanoparticle coating with OA by hydrothermal method. The phthalocyanines anchorage on the Fe3O4/OA core/shell nanomaterial was performed by facile and effective sonication method. The as obtained Fe3O4/OA/phthalocyanine hybrids were investigated by Fourier transform infrared spectroscopy, X-ray diffraction, UV-visible spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis and magnetic measurements. TEM showed round-shaped nanomaterials with sizes in the range of 12–15 nm. Nanomaterials presented saturation magnetization (Ms) in the 1–16 emu/g and superparamagnetic behavior. Furthermore, it was observed that the thermal stability of the samples was directly affected by the insertion of different transition metals in the ring cavity of the phthalocyanine molecule. Full article
(This article belongs to the Special Issue Phthalocyanines and Their Analogues: Something Old, Something New)
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Review

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51 pages, 10538 KiB  
Review
Applications of Photoinduced Phenomena in Supramolecularly Arranged Phthalocyanine Derivatives: A Perspective
by Simona Bettini, Ludovico Valli and Gabriele Giancane
Molecules 2020, 25(16), 3742; https://doi.org/10.3390/molecules25163742 - 16 Aug 2020
Cited by 11 | Viewed by 4626
Abstract
This review focuses on the description of several examples of supramolecular assemblies of phthalocyanine derivatives differently functionalized and interfaced with diverse kinds of chemical species for photo-induced phenomena applications. In fact, the role of different substituents was investigated in order to tune peculiar [...] Read more.
This review focuses on the description of several examples of supramolecular assemblies of phthalocyanine derivatives differently functionalized and interfaced with diverse kinds of chemical species for photo-induced phenomena applications. In fact, the role of different substituents was investigated in order to tune peculiar aggregates formation as well as, with the same aim, the possibility to interface these derivatives with other molecular species, as electron donor and acceptor, carbon allotropes, cyclodextrins, protein cages, drugs. Phthalocyanine photo-physical features are indeed really interesting and appealing but need to be preserved and optimized. Here, we highlight that the supramolecular approach is a versatile method to build up very complex and functional architectures. Further, the possibility to minimize the organization energy and to facilitate the spontaneous assembly of the molecules, in numerous examples, has been demonstrated to be more useful and performing than the covalent approach. Full article
(This article belongs to the Special Issue Phthalocyanines and Their Analogues: Something Old, Something New)
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