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Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021
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Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021

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

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 14979

Special Issue Editors

Dr. João P. C. Tomé

E-Mail Website
Guest Editor
Centro de Química Estrutural, Institute of Molecular Science and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, 1049-001 Lisboa, Portugal
Interests: (photo)active (hybrid)materials; porphyrins; phthalocyanines; photomedicine; photoinduced energy; electron-transfer materials; optical (chemo)sensors; (photo)catalysis
Special Issues, Collections and Topics in MDPI journals
Dr. Augusto C. Tomé

E-Mail Website
Guest Editor
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: synthesis and functionalization of porphyrins, phthalocyanines and porphyrin-type compounds; photodynamic therapy; photoinactivation of microorganisms; chemical sensing; solar cells
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues, 

Natural and synthetic porphyrin derivatives, phthalocyanines, and other porphyrin-type compounds (corroles, expanded porphyrins, pyrrole-modified porphyrins, calixpyrroles, etc.) are extremely interesting compounds, both in terms of their chemistry and applications. New methods for their synthesis or structural modification are continuously being discovered, and an increasing number of molecules of these types are finding application in medicine (e.g., PDT, theranostic, imaging), solar cells, sensors, molecular recognition, catalysis, etc. The aim of this Special Issue is to provide a broad survey of the most recent developments related with the chemistry, properties, and applications of these compounds. Articles reporting recent original discoveries or reviews are welcome.

Prof. Dr. João Paulo C. Tomé
Dr. Augusto C. Tomé
Guest Editors

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Published Papers (6 papers)

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Research

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15 pages, 2495 KiB  
Article
Cationic Axial Ligand Effects on Sulfur-Substituted Subphthalocyanines
by Yusaku Ogura, Masahiro Nakano, Hajime Maeda, Masahito Segi and Taniyuki Furuyama
Molecules 2022, 27(9), 2766; https://doi.org/10.3390/molecules27092766 - 26 Apr 2022
Cited by 2 | Viewed by 2438
Abstract
Herein, we report the synthesis of sulfur-substituted boron(III) subphthalocyanines (SubPcs) with cationic axial ligands. Subphthalocyanines were synthesized by a condensation reaction using the corresponding phthalonitriles and boron trichloride as a template. An aminoalkyl group was introduced on the central boron atom; this process [...] Read more.
Herein, we report the synthesis of sulfur-substituted boron(III) subphthalocyanines (SubPcs) with cationic axial ligands. Subphthalocyanines were synthesized by a condensation reaction using the corresponding phthalonitriles and boron trichloride as a template. An aminoalkyl group was introduced on the central boron atom; this process was followed by N-methylation to introduce a cationic axial ligand. The peripheral sulfur groups shifted the Q band of SubPcs to a longer wavelength. The cationic axial ligands increased the polarity and enhanced the hydrophilicity of SubPcs. The effect of axial ligands on absorption and fluorescence properties is generally small. However, a further red shift was observed by introducing cationic axial ligands into the sulfur-substituted SubPcs. This change is similar to that in sulfur-substituted silicon(IV) phthalocyanines. The unique effect of the cationic axial ligand was extensively investigated by theoretical calculations and electrochemistry. In particular, the precise oxidation potential was determined using ionization potential measurements. Thus, the results of the present study provide a novel strategy for developing functional dyes and pigments based on SubPcs. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021)
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13 pages, 2250 KiB  
Article
Self-Assembly-Directed Exciton Diffusion in Solution-Processable Metalloporphyrin Thin Films
by Abhishek Shibu, Camilla Middleton, Carly O. Kwiatkowski, Meesha Kaushal, Jonathan H. Gillen and Michael G. Walter
Molecules 2022, 27(1), 35; https://doi.org/10.3390/molecules27010035 - 22 Dec 2021
Cited by 1 | Viewed by 2516
Abstract
The study of excited-state energy diffusion has had an important impact in the development and optimization of organic electronics. For instance, optimizing excited-state energy migration in the photoactive layer in an organic solar cell device has been shown to yield efficient solar energy [...] Read more.
The study of excited-state energy diffusion has had an important impact in the development and optimization of organic electronics. For instance, optimizing excited-state energy migration in the photoactive layer in an organic solar cell device has been shown to yield efficient solar energy conversion. Despite the crucial role that energy migration plays in molecular electronic device physics, there is still a great deal to be explored to establish how molecular orientation impacts energy diffusion mechanisms. In this work, we have synthesized a new library of solution-processable, Zn (alkoxycarbonyl)phenylporphyrins containing butyl (ZnTCB4PP), hexyl (ZnTCH4PP), 2-ethylhexyl (ZnTCEH4PP), and octyl (ZnTCO4PP) alkoxycarbonyl groups. We establish that, by varying the length of the peripheral alkyl chains on the metalloporphyrin macrocycle, preferential orientation and molecular self-assembly is observed in solution-processed thin films. The resultant arrangement of molecules consequently affects the electronic and photophysical characteristics of the metalloporphyrin thin films. The various molecular arrangements in the porphyrin thin films and their resultant impact were determined using UV-Vis absorption spectroscopy, steady-state and time-resolved fluorescence emission lifetimes, and X-ray diffraction in thin films. The films were doped with C60 quencher molecules and the change in fluorescence was measured to derive a relative quenching efficiency. Using emission decay, relative quenching efficiency, and dopant volume fraction as input, insights on exciton diffusion coefficient and exciton diffusion lengths were obtained from a Monte Carlo simulation. The octyl derivative (ZnTCO4PP) showed the strongest relative fluorescence quenching and, therefore, the highest exciton diffusion coefficient (5.29 × 10−3 cm2 s−1) and longest exciton diffusion length (~81 nm). The octyl derivative also showed the strongest out-of-plane stacking among the metalloporphyrins studied. This work demonstrates how molecular self-assembly can be used to modulate and direct exciton diffusion in solution-processable metalloporphyrin thin films engineered for optoelectronic and photonic applications. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021)
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14 pages, 2405 KiB  
Article
Double-PEGylated Cyclopeptidic Photosensitizer Prodrug Improves Drug Uptake from In Vitro to Hen’s Egg Chorioallantoic Membrane Model
by Jordan Bouilloux, Martin Kiening, Sopie Yapi and Norbert Lange
Molecules 2021, 26(20), 6241; https://doi.org/10.3390/molecules26206241 - 15 Oct 2021
Cited by 1 | Viewed by 1729
Abstract
Cyclopeptidic photosensitizer prodrugs (cPPPs) are compounds designed to specifically target overexpressed hydrolases such as serine proteases, resulting in their specific activation in close proximity to tumor cells. In this study, we explored a series of conjugates that can be selectively activated by the [...] Read more.
Cyclopeptidic photosensitizer prodrugs (cPPPs) are compounds designed to specifically target overexpressed hydrolases such as serine proteases, resulting in their specific activation in close proximity to tumor cells. In this study, we explored a series of conjugates that can be selectively activated by the urokinase plasminogen activator (uPA). They differ from each other by their pheophorbide a (Pha) loading, their number of PEG chains and the eventual presence of black hole quenchers (BHQ3). The involvement of a peptidic linker between the drugs and the cyclopeptidic carrier allows specific cleavage by uPA. Restoration of the photophysical activity was observed in vitro on A549 lung and MCF7 breast cancer cells that exhibited an increase in red fluorescence emission up to 5.1-fold and 7.8-fold, respectively for uPA-cPPQ2+2/5. While these cPPP conjugates do not show dark toxicity, they revealed their phototoxic potential in both cell lines at 5 µM of Phaeq and a blue light fluence of 12.7 J/cm2 that resulted in complete cell death with almost all conjugates. This suggests, in addition to the promising use for cancer diagnosis, a use as a PDT agent. Intravenous injection of tetrasubstituted conjugates in fertilized hen eggs bearing a lung cancer nodule (A549) showed that a double PEGylation was favorable for the selective accumulation of the unquenched Pha moieties in the tumor nodules. Indeed, the diPEGylated uPA-cPPP4/52 induced a 5.2-fold increase in fluorescence, while the monoPEGylated uPA-cPPP4/5 or uPA-cPPQ2+2/5 led to a 0.4-fold increase only. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021)
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19 pages, 4245 KiB  
Article
Porphyrin–Schiff Base Conjugates Bearing Basic Amino Groups as Antimicrobial Phototherapeutic Agents
by María E. Pérez, Javier E. Durantini, Eugenia Reynoso, María G. Alvarez, María E. Milanesio and Edgardo N. Durantini
Molecules 2021, 26(19), 5877; https://doi.org/10.3390/molecules26195877 - 28 Sep 2021
Cited by 19 | Viewed by 2693
Abstract
New porphyrin–Schiff base conjugates bearing one (6) and two (7) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(N,N-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive [...] Read more.
New porphyrin–Schiff base conjugates bearing one (6) and two (7) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(N,N-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission (ΦF ~ 0.12) in N,N-dimethylformamide. Porphyrins 6 and 7 photosensitized the generation of O2(1Δg) (ΦΔ ~ 0.44) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly mediated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photodynamic action through a reaction with O2(1Δg) to produce iodine. The photodynamic inactivation capacity induced by porphyrins 6 and 7 was evaluated in Staphylococcus aureus, Escherichia coli, and Candida albicans. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021)
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10 pages, 3213 KiB  
Article
Spectrophotometric Study of Bridging N-Donor Ligand-Induced Supramolecular Assembly of Conjugated Zn-Trisporphyrin with a Triphenylamine Core
by Nirmal K. Shee, Ju-Won Seo and Hee-Joon Kim
Molecules 2021, 26(16), 4771; https://doi.org/10.3390/molecules26164771 - 6 Aug 2021
Cited by 13 | Viewed by 2112
Abstract
This article studies the supramolecular assembly behavior of a Zn-trisporphyrin conjugate containing a triphenylamine core (1) with bridging N-donor ligands using the UV-vis spectrophotometric titration method at micromolar concentrations. Our results show that pyridine, a non-bridging ligand, formed a 3:1 [...] Read more.
This article studies the supramolecular assembly behavior of a Zn-trisporphyrin conjugate containing a triphenylamine core (1) with bridging N-donor ligands using the UV-vis spectrophotometric titration method at micromolar concentrations. Our results show that pyridine, a non-bridging ligand, formed a 3:1 open complex with 1. The corresponding binding constant was estimated to be (2.7 ± 0.15) × 1014 M−3. In contrast, bridging ligands, 4,4-bipyridine (BIPY) and 1,3-di(4-pyridyl)propane (DPYP), formed stable 3:2 double-decker complexes with 1 in solution, which collapsed to yield a 3:1 open complex when excess BIPY or DPYP was added. The binding constants for forming BIPY and DPYP double-decker complexes were estimated to be (9.26 ± 0.07) × 1027 M−4 and (3.62 ± 0.16) × 1027 M−4, respectively. The UV-vis titration profiles supported the conclusion that the degradation of the 3:2 double-decker 1∙BIPY complex is less favorable compared to that of 1∙DPYP. Consequently, the formation of the 3:1 1∙DPYP open complex proceeded more readily than that of 1∙BIPY. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021)
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Review

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15 pages, 1843 KiB  
Review
Porphyrins as Chelating Agents for Molecular Imaging in Nuclear Medicine
by Krystyna Pyrzynska, Krzysztof Kilian and Mateusz Pęgier
Molecules 2022, 27(10), 3311; https://doi.org/10.3390/molecules27103311 - 21 May 2022
Cited by 10 | Viewed by 2405
Abstract
Porphyrin ligands, showing a significant affinity for cancer cells, also have the ability to chelate metallic radioisotopes to form potential diagnostic radiopharmaceuticals. They can be applied in single-photon emission computed tomography (SPECT) and positron emission tomography (PET) to evaluate metabolic changes in the [...] Read more.
Porphyrin ligands, showing a significant affinity for cancer cells, also have the ability to chelate metallic radioisotopes to form potential diagnostic radiopharmaceuticals. They can be applied in single-photon emission computed tomography (SPECT) and positron emission tomography (PET) to evaluate metabolic changes in the human body for tumor diagnostics. The aim of this paper is to present a short overview of the main metallic radionuclides complexed by porphyrin ligands and used in these techniques. These chelation reactions are discussed in terms of the complexation conditions and kinetics and the complex stability. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications 2021)
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