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Porphyrin Analogues: From Synthesis to Application
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Porphyrin Analogues: From Synthesis to Application

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

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 6343

Special Issue Editor

Prof. Dr. Johannes A. A. W. Elemans

E-Mail Website
Guest Editor
Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
Interests: supramolecular chemistry; (metal-)organic synthesis; porphyrins; catalysis; surface chemistry; scanning probe microscopy
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Porphyrins play a prominent role in nature, e.g., in light harvesting, oxygen transport, and enzyme-mediated catalysis. In the past few decades, the development of efficient synthetic methodologies of these macrocyclic dyes has established a research field in which porphyrins and their derivatives have also found a wide range of applications in the chemical, physical, and medical sciences. The versatility of porphyrins is primarily based on their ease of chemical functionalization and their ability to coordinate virtually all transition metals in their core, providing them with a broad potential of applications, as well as their integration in molecular and supramolecular structures and as components of materials and devices. In this Special Issue, we welcome contributions (articles and reviews) dealing with recent developments in porphyrin chemistry, with a special focus on new synthetic methodologies and the application of porphyrin derivatives in areas of catalysis, sensing, optics, and electronics.

Prof. Dr. Johannes A. A. W. Elemans
Guest Editor

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Keywords

  • Porphyrin derivatives
  • Porphyrin synthesis
  • (Photo)catalysis
  • Porphyrin-based host-guest chemistry
  • Supramolecular materials
  • Photoactive (nano)materials
  • Self-assembly
  • Sensors
  • Molecular electronics
  • (Nonlinear) optics

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Published Papers (2 papers)

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19 pages, 6285 KiB  
Article
Synthesis, Characterization, DFT and Photocatalytic Studies of a New Pyrazine Cadmium(II) Tetrakis(4-methoxy-phenyl)-porphyrin Compound
by Chadlia Mchiri, Louis-Charl C. Coetzee, Faycal Chandoul, Abdesslem Jedidi, Adedapo S. Adeyinka, Nomampondo Magwa, Thierry Roisnel, Sana Ben Moussa and Habib Nasri
Molecules 2022, 27(12), 3833; https://doi.org/10.3390/molecules27123833 - 14 Jun 2022
Cited by 6 | Viewed by 2752
Abstract
This study describes the synthesis, theoretical investigations, and photocatalytic degradational properties of a new (pyrazine)(meso-tetrakis(4-tert-methoxyphenyl)-porphyrinato)-cadmium (II) ([Cd(TMPP)-Pyz]) complex (1). The new penta-coordinated CdII porphyrin complex (1) was characterized by various spectroscopic techniques, including FT-IR, NMR, UV-visible absorption, fluorescence [...] Read more.
This study describes the synthesis, theoretical investigations, and photocatalytic degradational properties of a new (pyrazine)(meso-tetrakis(4-tert-methoxyphenyl)-porphyrinato)-cadmium (II) ([Cd(TMPP)-Pyz]) complex (1). The new penta-coordinated CdII porphyrin complex (1) was characterized by various spectroscopic techniques, including FT-IR, NMR, UV-visible absorption, fluorescence emission, and singlet oxygen, while its molecular structure was studied using single crystal X-ray diffraction. The UV–Vis spectroscopic study highlighted the redshift of the absorption bands after the insertion of the Cd(II) metal ion into the TMPP ring. The co-coordination of the pyrazine axial ligand enhanced this effect. A fluorescence emission spectroscopic study showed a significant blueshift in the Q bands, accompanied by a decrease in the fluorescence emission intensity and quantum yields of Φf = 0.084, Φf = 0.06 and Φf = 0.03 for H2-TMPP free-base porphyrin, [Cd(TMPP)] and [Cd(TMPP)(Pyz)] (1) respectively. Singlet oxygen revealed that the H2-TMPP porphyrin produced the most efficient singlet oxygen quantum yield of (ΦΔ = 0.73) compared to [CdTMPP] (ΦΔ = 0.57) and [Cd(TMPP)(Pyz)] (1) (ΦΔ = 0.13). In the crystal lattice, the [Cd(TMPP)Pyz] was stabilized through non-covalent intermolecular interactions (NCI), such as the hydrogen bonds C-H···N and C-H···Cg. Additionally, crystal explorer software was then utilized to measure the quantitative analysis of the intermolecular interactions in the unit cell of the crystal structure and established that the C-H···π interaction dominated. The Natural bond orbital (NBO) analysis revealed that each molecule is stabilized by hyperconjugation and charge delocalization. As a photocatalyst, the coordination complex 1 showed excellent photocatalytic activity toward the degradation of Levafix Blue CA reactive dye (i.e., dye photo-degradation of 80%). Full article
(This article belongs to the Special Issue Porphyrin Analogues: From Synthesis to Application)
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13 pages, 3483 KiB  
Article
Wet-Chemically Prepared Porphyrin Layers on Rutile TiO2(110)
by Daniel Wechsler, Cynthia Carolina Fernández, Julia Köbl, Lisa-Marie Augustin, Corinna Stumm, Norbert Jux, Hans-Peter Steinrück, Federico José Williams and Ole Lytken
Molecules 2021, 26(10), 2871; https://doi.org/10.3390/molecules26102871 - 12 May 2021
Cited by 5 | Viewed by 2937
Abstract
Porphyrins are large organic molecules that are interesting for different applications, such as photovoltaic cells, gas sensors, or in catalysis. For many of these applications, the interactions between adsorbed molecules and surfaces play a crucial role. Studies of porphyrins on surfaces typically fall [...] Read more.
Porphyrins are large organic molecules that are interesting for different applications, such as photovoltaic cells, gas sensors, or in catalysis. For many of these applications, the interactions between adsorbed molecules and surfaces play a crucial role. Studies of porphyrins on surfaces typically fall into one of two groups: (1) evaporation onto well-defined single-crystal surfaces under well-controlled ultrahigh vacuum conditions or (2) more application-oriented wet chemical deposition onto less well-defined high surface area surfaces under ambient conditions. In this study, we will investigate the wet chemical deposition of 5-(monocarboxyphenyl)-10,15,20-triphenylporphyrin (MCTPP) on well-defined rutile TiO2(110) single crystals under ambient conditions. Prior to deposition, the TiO2(110) crystals were also cleaned wet-chemically under ambient conditions, meaning none of the preparation steps were done in ultrahigh vacuum. However, after each preparation step, the surfaces were characterized in ultrahigh vacuum with X-ray photoelectron spectroscopy (XPS) and the result was compared with porphyrin layers prepared in ultrahigh vacuum (UHV) by evaporation. The differences of both preparations when exposed to zinc ion solutions will also be discussed. Full article
(This article belongs to the Special Issue Porphyrin Analogues: From Synthesis to Application)
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