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Tetrapyrroles, Porphyrins and Phthalocyanines II

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

Deadline for manuscript submissions: closed (30 August 2021) | Viewed by 4881

Special Issue Editor


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Guest Editor
Department of Engineering for Innovation, University of Salento, Via Monteroni, 73100 Lecce, Italy
Interests: functional green materials and processes; materials from renewables; nanomaterials; (photo)catalysis; organic/inorganic hybrids
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Special Issue Information

Dear Colleagues,

This Special Issue on “Tetrapyrroles, Porphyrins and Phthalocyanines II” will offer an attractive forum to present recent results concerning the synthesis and characterization of these classes of macrocyclic compounds devoted to the preparation of novel functional materials and their utilization to perform innovative processes.

Prof. Dr. Giuseppe Mele
Guest Editor

Manuscript Submission Information

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Keywords

  • tetrapyrroles
  • porphyrins
  • phthalocyanines
  • (photo) catalytic processes
  • (semi)conductors/(metal)organic hybrids
  • coatings
  • drug delivery systems
  • dyes
  • electrophotocatalysis
  • functional materials
  • lanthanides
  • liquid phase processes
  • materials from renewables
  • metal organic
  • metal organic frameworks (MOFs)
  • organic/inorganic hybrids
  • removal of pollutants
  • sensitizers
  • surface functionalization
  • UV-light
  • vapour phase processes
  • visible light

Published Papers (2 papers)

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Research

17 pages, 4550 KiB  
Article
A Comparative Study of the Semiconductor Behavior of Organic Thin Films: TCNQ-Doped Cobalt Phthalocyanine and Cobalt Octaethylporphyrin
by María Elena Sánchez-Vergara, Citlalli Rios, Omar Jiménez-Sandoval and Roberto Salcedo
Molecules 2020, 25(24), 5800; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25245800 - 09 Dec 2020
Cited by 2 | Viewed by 2148
Abstract
The structure formed by cobalt phthalocyanine (CoPc) and cobalt octaethylporphyrin (CoOEP) with electron-acceptor tetracyano-π-quinodimethane (TCNQ), was studied by Density Functional Theory (DFT) methods. According to theoretical calculations, both cobalt systems can establish dispersion forces related to TCNQ and also in both cases the [...] Read more.
The structure formed by cobalt phthalocyanine (CoPc) and cobalt octaethylporphyrin (CoOEP) with electron-acceptor tetracyano-π-quinodimethane (TCNQ), was studied by Density Functional Theory (DFT) methods. According to theoretical calculations, both cobalt systems can establish dispersion forces related to TCNQ and also in both cases the link between them is built by means of hydrogen bonds. Based on the results of these DFT calculations, we developed experimental work: the organic semiconductors were doped, and the thermal evaporation technique was used to prepare semiconductor thin films of such compounds. The structure of the films was studied by FTIR and Raman spectroscopy. The optical properties of the CoPc-TCNQ and CoOEP-TCNQ films were investigated by means of UV-Vis measurements. The results obtained were used to estimate the type of transitions and the optical bandgap. The results were compared to the previously calculated theoretical bandgap. The CoOEP-TCNQ film presented the smallest theoretical and experimental bandgap. Finally, the electrical properties of the organic semiconductors were evaluated from a PET (polyethylene terephthalate)/indium tin oxide (ITO)/cobalt macrocycle-TCNQ/silver (Ag) device we prepared. The CoOEP-TCNQ-based device showed an ohmic behavior. The device manufactured from CoPc-TCNQ also showed an ohmic behavior at low voltages, but significantly changed to SCLC (space-charge limited conductivity) at high voltage values. Full article
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines II)
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15 pages, 2633 KiB  
Article
Hydrogen Bond-Mediated Conjugates Involving Lanthanide Diphthalocyanines and Trifluoroacetic Acid (Lnpc2@TFA): Structure, Photoactivity, and Stability
by Gabriela Dyrda, Maja Zakrzyk, Małgorzata A. Broda, Tomasz Pędziński, Giuseppe Mele and Rudolf Słota
Molecules 2020, 25(16), 3638; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25163638 - 10 Aug 2020
Cited by 9 | Viewed by 2286
Abstract
The interaction between lanthanide diphthalocyanine complexes, LnPc2 (Ln = Nd, Sm, Eu, Gd, Yb, Lu; Pc = C32H16N8, phthalocyanine ligand) and trifluoroacetic acid (TFA) was investigated in benzene, and the stability of the resulting molecular system [...] Read more.
The interaction between lanthanide diphthalocyanine complexes, LnPc2 (Ln = Nd, Sm, Eu, Gd, Yb, Lu; Pc = C32H16N8, phthalocyanine ligand) and trifluoroacetic acid (TFA) was investigated in benzene, and the stability of the resulting molecular system was assessed based on spectral (UV-Vis) and kinetic measurements. Structural Density Functional Theory (DFT) calculations provided interesting data regarding the nature of the bonding and allowed estimating the interaction energy between the LnPc2 and TFA species. Conjugates are created between the LnPc2 and TFA molecules via hydrogen bonds of moderate strength (>N∙∙H··) at the meso- -bridges of the Pc moieties, which renders the sandwich system to flatten. Attachment of TFA is followed by rearrangement of electronic density within the chromophore system of the macrocycles manifested in considerable changes in their UV-Vis spectra and consequently the color of the studied solutions (from green to orange). The LnPc2@TFA conjugates including Nd, Sm, Eu, and Gd appeared evidently less photostable when exposed to UV radiation than the related mother compounds, whereas in the case of Yb and Lu derivatives some TFA-prompted stabilizing effect was noticed. The conjugates displayed the capacity for singlet oxygen generation in contrast to the LnPc2s itself. Photon upconversion through sensitized triplet–triplet annihilation was demonstrated by the TFA conjugates of Nd, Sm, Eu, and Gd. Full article
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines II)
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