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Phthalocyanines and Porphyrins

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

Deadline for manuscript submissions: closed (15 February 2021) | Viewed by 39200

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Special Issue Editors

Prof. Dr. M. Salomé Rodríguez-Morgade

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Guest Editor

Universidad Autónoma de Madrid, Madrid, Spain
Interests: organic Synthesis; phthalocyanines; subporphyrazines; porphyrazines; subphthalocyanines; expanded analogues; molecular photovoltaics; PDT; artificial photosynthesis

Prof. Dr. Soji Shimizu

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Guest Editor

Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 890-0395, Japan
Interests: porphyrin and phthalocyanine Chemistry; BODIPY; supramolecular Chemistry; near-infrared chromophores; photophysics

Special Issue Information

Dear Colleagues,

We are happy to be Guest Editors of this Special Issue of Molecules, dedicated to “Porphyrins and Phthalocyanines”. Porphyrins constitute a family of macrocycles that are ubiquitous in nature, playing important roles in numerous biological functions. Their 18 p-electron, aromatic, tetrapyrrolic structure represents far more than the sum of its parts, giving rise to a variety of physicochemical properties that cannot be deduced from those of pyrroles. Although the beginnings of porphyrin chemistry can be traced back to Hans Fischer in the 1930s, the synthesis of these macrocycles, as well as the preparation of new congeners, has been a matter of continuing scientific interest. Phthalocyanines represent the best known synthetic porphyrin analogues, being one of the most widely studied macrocyclic compounds. In addition, the synthesis of expanded, contracted, and intrinsically unsymmetrical porphyrin and phthalocyanine analogues remains an expanding topic. The scope of porphyrin science is enormous, ranging from chemical synthesis and molecular characterization to supramolecular organization, spectroscopy, electrochemistry, bioinorganic chemistry, photochemistry and photophysics, clinical medicine, and materials science, among others. This Special Issue is aimed at covering recent advances in the synthesis, characterization, and applications of porphyrins, phthalocyanines, and their analogues. We hope that these fields will be represented by both reviews and original chemical research reports that represent your contributions to this volume.

Prof. M. Salomé Rodríguez-Morgade
Prof. Soji Shimizu
Guest Editors

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Keywords

porphyrin
phthalocyanine
porphyrazine
contracted porphyrins and phthalocyanines
expanded porphyrins and phthalocyanines
synthesis
supramolecular organization
photophysics
photochemistry
applications

Published Papers (14 papers)

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Research

Jump to: Review

17 pages, 6833 KiB

Open AccessArticle

Molecular Dynamics of Cobalt Protoporphyrin Antagonism of the Cancer Suppressor REV-ERBβ

by Taufik Muhammad Fakih, Fransiska Kurniawan, Muhammad Yusuf, Mudasir Mudasir and Daryono Hadi Tjahjono

Molecules 2021, 26(11), 3251; https://doi.org/10.3390/molecules26113251 - 28 May 2021

Cited by 2 | Viewed by 3138

Abstract

Nuclear receptor REV-ERBβ is an overexpressed oncoprotein that has been used as a target for cancer treatment. The metal-complex nature of its ligand, iron protoporphyrin IX (Heme), enables the REV-ERBβ to be used for multiple therapeutic modalities as a photonuclease, a photosensitizer, or a fluorescence imaging agent. The replacement of iron with cobalt as the metal center of protoporphyrin IX changes the ligand from an agonist to an antagonist of REV-ERBβ. The mechanism behind that phenomenon is still unclear, despite the availability of crystal structures of REV-ERBβ in complex with Heme and cobalt protoporphyrin IX (CoPP). This study used molecular dynamic simulations to compare the effects of REV-ERBβ binding to Heme and CoPP, respectively. The initial poses of Heme and CoPP in complex with agonist and antagonist forms of REV-ERBβ were predicted using molecular docking. The binding energies of each ligand were calculated using the MM/PBSA method. The computed binding affinity of Heme to REV-ERBβ was stronger than that of CoPP, in agreement with experimental results. CoPP altered the conformation of the ligand-binding site of REV-ERBβ, disrupting the binding site for nuclear receptor corepressor, which is required for REV-ERBβ to regulate the transcription of downstream target genes. Those results suggest that a subtle change in the metal center of porphyrin can change the behavior of porphyrin in cancer cell signaling. Therefore, modification of porphyrin-based agents for cancer therapy should be conducted carefully to avoid triggering unfavorable effects. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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18 pages, 4016 KiB

Open AccessArticle

Tuning the Acceptor Unit of Push–Pull Porphyrazines for Dye-Sensitized Solar Cells

by Diana-Paola Medina, Javier Fernández-Ariza, Maxence Urbani, Frédéric Sauvage, Tomás Torres and M. Salomé Rodríguez-Morgade

Molecules 2021, 26(8), 2129; https://doi.org/10.3390/molecules26082129 - 7 Apr 2021

Cited by 3 | Viewed by 2149

Abstract

A family of four push–pull porphyrazines of A₃B type, where each unit A contains two peripheral propyl chains and the unit B is endowed with a carboxylic acid, were prepared. The carboxylic acid was attached to the β-position of the pyrrolic unit, either directly (Pz 10), or through cyanovinyl (Pz 11) and phenyl (Pz 7) groups. The fourth Pz (14) consisted in a pyrazinoporphyrazine wherein the dinitrogenated heterocycle provided intrinsic donor–acceptor character to the macrocycle and contained a carboxyphenyl substituent. The direct attachment of the carboxylic acid functions and their linkers to the porphyrazine core produces stronger perturbation on the electronic properties of the macrocycle, with respect to their connection through fused benzene or pyrazine rings in TT112 and 14, respectively. The HOMO and LUMO energies of the Pzs, which were estimated with DFT calculations, show little variation within the series, except upon introduction of the cyanovinyl spacer, which produces a decrease in both frontier orbital energetic levels. This effective interaction of cyanovinyl substitution with the macrocycle is also evidenced in UV/Vis spectroscopy, where a large splitting of the Q-band indicates strong desymmetrization of the Pz. The performance of the four Pzs as photosensitizers in DSSCs were also investigated. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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12 pages, 1296 KiB

Open AccessArticle

Sustainable Approaches to the Synthesis of Metallophthalocyanines in Solution

by Gloria Zanotti, Patrizia Imperatori, Anna Maria Paoletti and Giovanna Pennesi

Molecules 2021, 26(6), 1760; https://doi.org/10.3390/molecules26061760 - 21 Mar 2021

Cited by 7 | Viewed by 2695

Abstract

This work aims to investigate more sustainable reaction conditions for the synthesis of metallophthalocyanines. Anisole, glycerol and their mixtures have been investigated as reaction media for the tetramerization of phthalonitriles. Acetates of three divalent first-transition metal cations, Co(II), Cu(II) and Zn(II), were used and several bases were tested, depending on the chosen substrates and reaction conditions, with a view to making the whole process more sustainable while ensuring its scalability. Unsubstituted phthalocyanines were synthesized to analyze the behavior of the different metal ions in terms of reactivity in the new reaction media, resulting in a general Cu > Co > Zn trend, while the nonpolar tetra-tert-butyl substitution was investigated to evaluate the synthesis of soluble derivatives in the new conditions. Furthermore, the potassium hydroxide (KOH)-aided statistical synthesis of the unsymmetrical 9(10), 16(17), 23(24)-tri-tert-butyl-2-iodophthalocyaninato zinc(II), starting from 4-tert-butylphthalonitrile and 4-iodophthalonitrile in a glycerol/anisole mixture, proceeded with a satisfactory 26% yield. Our results provide insights into the investigation of new reaction environments and the understanding of their strengths and weaknesses, with a view to further increasing the sustainability of the synthesis of metallomacrocycles with high added value while lowering their production cost. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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11 pages, 3819 KiB

Open AccessArticle

Periphery-Fused Chiral A₂B-Type Subporphyrin

by Shoma Hirokawa, Nagao Kobayashi and Soji Shimizu

Molecules 2021, 26(4), 1140; https://doi.org/10.3390/molecules26041140 - 20 Feb 2021

Cited by 3 | Viewed by 1790

Abstract

Despite significant interest, the chiroptical properties of subporphyrins have rarely been investigated because chiral subporphyrins are elusive. Here, inherently chiral subporphyrins are elaborated by forming a fused pyran ring at the periphery of an A₂B-type meso-aryl-substituted subporphyrin. Their circular dichroism (CD) properties are largely affected by the peripheral substituents and the dihedral angles between the meso-aryl substituents and the subporphyrin core: the β-perbromo subporphyrin with an orthogonal arrangement of the meso-phenyl substituents to the subporphyrin core exhibits weak CD signals corresponding to the Q bands, whereas the unsubstituted species with smaller dihedral angles shows relatively intense CD signals. A detailed structure–property relationship of these chiral subporphyrins was elucidated by time-dependent (TD) DFT calculations. This study reveals that the CD properties of chiral subporphyrins can be controlled by peripheral substitution and meso-aryl substituents. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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12 pages, 3424 KiB

Open AccessCommunication

Mapping the Chiroptical Properties of Local Domains in Thin Films of Chiral Silicon Phthalocyanines by CD Imaging

by Dora-M. Răsădean, Tiberiu-M. Gianga, Tamás Jávorfi, Rohanah Hussain, Giuliano Siligardi and G. Dan Pantoș

Molecules 2020, 25(24), 6048; https://doi.org/10.3390/molecules25246048 - 21 Dec 2020

Cited by 5 | Viewed by 2276

Abstract

The first example of uniformly chiral thin films of silicon phthalocyanines (SiPcs) are reported. The local domains of the films are mapped using circular dichroism (CD) imaging (CDi) technique available at the Diamond B23 beamline. The CDi allowed us to increase the spatial resolution up to 525× when compared with benchtop spectrometers. The results indicate formation on-surface of chiral and stable supramolecular assemblies with homogenous distribution. Chemical functionalization and solvent choice for deposition allow controllable chiroptical properties to be obtained. The method and technique reported in this work could be applied to prepare and characterize a wide variety of chiral thin films. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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13 pages, 1625 KiB

Open AccessArticle

Condition-Dependent Coordination and Peroxidase Activity of Hemin-Aβ Complexes

by Chiara Bacchella, James T. Brewster II, Steffen Bähring, Simone Dell’Acqua, Harrison D. Root, Gregory D. Thiabaud, James F. Reuther, Enrico Monzani, Jonathan L. Sessler and Luigi Casella

Molecules 2020, 25(21), 5044; https://doi.org/10.3390/molecules25215044 - 30 Oct 2020

Cited by 5 | Viewed by 2380

Abstract

The peroxidase activity of hemin-peptide complexes remains a potential factor in oxidative damage relevant to neurodegeneration. Here, we present the effect of temperature, ionic strength, and pH relevant to pathophysiological conditions on the dynamic equilibrium between high-spin and low-spin hemin-Aβ₄₀ constructs. This influence on peroxidase activity was also demonstrated using 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and dopamine (DA) oxidation rate analyses with increasing ratios of Aβ₁₆ and Aβ₄₀ (up to 100 equivalents). Interaction and reactivity studies of aggregated Aβ₄₀-hemin revealed enhanced peroxidase activity versus hemin alone. Comparison of the results obtained using Aβ₁₆ and Aβ₄₀ amyloid beta peptides revealed marked differences and provide insight into the potential effects of hemin-Aβ on neurological disease progression. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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10 pages, 4159 KiB

Open AccessCommunication

Selective Intramolecular Dehydrocyclization of Co-Porphyrin on Au(111)

by Cen Yin, Zhantao Peng, Dan Liu, Huanjun Song, Hao Zhu, Qiwei Chen and Kai Wu

Molecules 2020, 25(17), 3766; https://doi.org/10.3390/molecules25173766 - 19 Aug 2020

Cited by 7 | Viewed by 2808

Abstract

The on-surface C–H bond activation and coupling reaction is a powerful approach to constructing fine-tuned surface nanostructures. It is quite challenging to control its regioselectivity due to the inertness of the C–H bond involved. With scanning tunneling microscopy/spectroscopy and theoretical calculations, the C–H activation and sequential intramolecular dehydrocyclization of meso-tetra(p-methoxyphenyl)porphyrinatocobalt(II) was explored on Au(111), showing that the methoxy groups in the molecule could kinetically mediate the selectivity of the intramolecular reaction over its intermolecular coupling counterpart. The experimental results demonstrate that the introduced protecting group could help augment the selectivity of such on-surface reaction, which can be applied to the precise fabrication of functional surface nanostructures. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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14 pages, 5111 KiB

Open AccessArticle

NIR Absorbing AzaBODIPY Dyes for pH Sensing

by Gugu Kubheka, John Mack, Tebello Nyokong and Zhen Shen

Molecules 2020, 25(16), 3689; https://doi.org/10.3390/molecules25163689 - 13 Aug 2020

Cited by 7 | Viewed by 3380

Abstract

Two near-infrared (NIR) absorbing di(thien-2-nyl)-di(dimethylanilino)azaBODIPY dyes 2a and 2b were synthesized and characterized that differ depending on whether the dimethylaniline substituents are introduced at the 3,5- or 1,7-positions of the azaBODIPY core. The main spectral bands lie at 824 and 790 nm, respectively, in CH₂Cl₂. The effect of substituent position on the photophysical and pH sensing properties was analyzed through a comparison of the optical properties with the results of time-dependent density functional theory (TD-DFT) calculations. Protonation of the dimethylamino nitrogen atoms eliminates the intramolecular charge transfer properties of these compounds, and this results in a marked blue-shift of the main absorption bands to 696 and 730 nm, respectively, in CH₂Cl₂, and a fluorescence “turn-on” effect in the NIR region. The pH dependence studies reveal that the pK_a values of the non-protonated 2a and 2b molecules are ca. 6.9 (±0.05) and 7.3 (±0.05), respectively, while that of the monoprotonated species for both dyes is ca. 1.4 (±0.05) making them potentially suitable for use as colorimetric pH indicators under highly acidic conditions. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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14 pages, 2576 KiB

Open AccessArticle

Comparative Study of Conduction Mechanisms in Disodium Phthalocyanine-Based Organic Diodes for Flexible Electronics

by Leon Hamui, María Elena Sánchez-Vergara, N. Díaz-Ortega and Roberto Salcedo

Molecules 2020, 25(16), 3687; https://doi.org/10.3390/molecules25163687 - 13 Aug 2020

Cited by 8 | Viewed by 1923

Abstract

In the current work, flexible diodes with flat heterojunction and dispersed heterojunction architecture were manufactured with to study the behavior of thin films of disodium phthalocyanine (Na₂Pc). The thin film devices, using the electronic acceptor tetracyano-π-quinodimethane (TCNQ), were fabricated by high-vacuum thermal evaporation with annealing post-treatment in order to optimize their behavior. Theoretical calculations based on density functional theory (DFT) with dispersion force analysis were carried out in order to simulate molecular interactions and to establish the nature of the weak interactions between the Na₂Pc and TCNQ fragments. In the optimized structure of the coupled Na₂Pc-TCNQ, the electronic relationship between phthalocyanine and TCNQ was observed to be through hydrogen bonds with bond lengths of 2.94 and 3.13 Å. Dispersed heterojunction device current density values were considerably larger than those of the flat heterojunction device. Barrier heights of 1.024 and 0.909 eV and charge mobilities of 10⁻¹⁰ and 10⁻⁹ m²/Vs for the flat heterojunction device and the dispersed heterojunction device, respectively, were observed. A small effect was observed on the electrical properties by thermal annealing on the flat heterojunction device. The threshold voltage decreased from 1.203 to 1.147 V and φ_b decreased by 0.001 eV. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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14 pages, 3220 KiB

Open AccessFeature PaperArticle

A Leopard Cannot Change Its Spots: Unexpected Products from the Vilsmeier Reaction on 5,10,15-Tritolylcorrole

by Fabrizio Caroleo, Greta Petrella, Lorena Di Zazzo, Sara Nardis, Beatrice Berionni Berna, Daniel O. Cicero and Roberto Paolesse

Molecules 2020, 25(16), 3583; https://doi.org/10.3390/molecules25163583 - 6 Aug 2020

Cited by 3 | Viewed by 2542

Abstract

The reaction of 5,10,15-tritolylcorrole with 3-dimethylaminoacrolein (3-DMA) and POCl₃ gives a further example of the rebel reactivity of this contracted macrocycle. While no evidence was obtained for the formation of the expected β-acrolein corrole, the inner core substituted N21,N22-3-formylpropylcorrole and the 10-acrolein isocorrole were the reaction products. By increasing the temperature or the amount of the Vilsmeier reagent, the 10-isocorrole became the unique reaction product. The formation of the isocorrole by electrophilic attack of the Vilsmeier reagent to the 10-position of the corrole is unprecedented in the porphyrinoids field and it could pave the way for a novel route to the preparation of stable isocorroles. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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11 pages, 2117 KiB

Open AccessCommunication

Oxidation-Induced Detachment of Ruthenoarene Units and Oxygen Insertion in Bis-Pd(II) Hexaphyrin π-Ruthenium Complexes

by Akito Nakai, Takayuki Tanaka and Atsuhiro Osuka

Molecules 2020, 25(12), 2753; https://doi.org/10.3390/molecules25122753 - 15 Jun 2020

Cited by 1 | Viewed by 2384

Abstract

Two types of new bis-Pd(II) hexaphyrin π-ruthenium complexes are reported. A double-decker bis-Pd(II) hexaphyrin π-ruthenium complex 4 was obtained by oxidation-induced detachment of a ruthenoarene unit from the triple-decker complex 3 and oxygen-inserted triple-decker bis-Pd(II) hexaphyrin π-ruthenium complex 6 was obtained upon treatment of bis-Pd(II) [26]hexaphyrin 5 with [RuCl₂(p-cymene)]₂ under aerobic conditions. Although π-metal complexation of porphyrinoids often results in decreased global aromaticity due to the enhancement of local 6π aromatic segments, distinct aromatic characters were indicated for 4 and 6 by ¹H-NMR spectral and theoretical calculations. These results are accounted for in terms of possible resonance contributors of hexaphyrin di- and tetraanion ligands. Thus, π-metal coordination has been shown to be effective for modulation of the overall aromaticity. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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17 pages, 4494 KiB

Open AccessArticle

A Hybrid Nanomaterial Based on Single Walled Carbon Nanotubes Cross-Linked via Axially Substituted Silicon (IV) Phthalocyanine for Chemiresistive Sensors

by Maxim Polyakov, Victoria Ivanova, Darya Klyamer, Baybars Köksoy, Ahmet Şenocak, Erhan Demirbaş, Mahmut Durmuş and Tamara Basova

Molecules 2020, 25(9), 2073; https://doi.org/10.3390/molecules25092073 - 29 Apr 2020

Cited by 23 | Viewed by 3136

Abstract

In this work, the novel hybrid nanomaterial SWCNT/SiPc made of single walled carbon nanotubes (SWCNT) cross-linked via axially substituted silicon (IV) phthalocyanine (SiPc) was studied as the active layer of chemiresistive layers for the detection of ammonia and hydrogen. SWCNT/SiPc is the first example of a carbon-based nanomaterial in which an axially substituted phthalocyanine derivative is used as a linker. The prepared hybrid material was characterized by spectroscopic methods, thermogravimetry, scanning and transmission electron microscopies. The layers of the prepared hybrid were tested as sensors toward ammonia and hydrogen by a chemiresistive method at different temperatures and relative humidity as well as in the presence of interfering gases like carbon dioxide, hydrogen sulfide and volatile organic vapors. The hybrid layers exhibited the completely reversible sensor response to both gases at room temperature; the recovery time was 100–200 s for NH₃ and 50–120 s in the case of H₂ depending on the gas concentrations. At the relative humidity (RH) of 20%, the sensor response was almost the same as that measured at RH 5%, whereas the further increase of RH led to its 2–3 fold decrease. It was demonstrated that the SWCNT/SiPc layers can be successfully used for the detection of both NH₃ and H₂ in the presence of CO₂. On the contrary, H₂S was found to be an interfering gas for the NH₃ detection. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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11 pages, 2023 KiB

Open AccessArticle

In Vitro Anti-Leishmanial Effect of Metallic Meso-Substituted Porphyrin Derivatives against Leishmania braziliensis and Leishmania panamensis Promastigotes Properties

by Fabian Espitia-Almeida, Carlos Díaz-Uribe, William Vallejo, Doris Gómez-Camargo and Arnold R. Romero Bohórquez

Molecules 2020, 25(8), 1887; https://doi.org/10.3390/molecules25081887 - 19 Apr 2020

Cited by 20 | Viewed by 2642

Abstract

In this study, a family of porphyrins based on 5,10,15,20-Tetrakis(4-ethylphenyl)porphyrin (1, Ph) and six metallo-derivatives (Zn²⁺(2, Ph-Zn), Sn⁴⁺(3, Ph-Sn), Mn²⁺ (4, Ph-Mn), Ni²⁺ (5, Ph-Ni), Al³⁺ (6, Ph-Al), and V³⁺ (7, Ph-V)) were tested as photosensitizers for photodynamic therapy against Leishmania braziliensis and panamensis. The singlet oxygen quantum yield value (Φ_Δ) for (1–7) was measured using 1,3-diphenylisobenzofuran (DPBF) as a singlet oxygen trapping agent and 5,10,15,20-(tetraphenyl)-porphyrin (H2TPP) as a reference standard; besides, parasite viability was estimated by the MTT assay. After metal insertion into the porphyrin core, the Φ_Δ increased from 0.76–0.90 and cell viability changed considerably. The Φ_Δ and metal type changed the cytotoxic activity. Finally, (2) showed both the highest Φ_Δ (0.90) and the best photodynamic activity against the parasites studied (IC₅₀ of 1.2 μM). Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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Review

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28 pages, 5907 KiB

Open AccessReview

BODIPY- and Porphyrin-Based Sensors for Recognition of Amino Acids and Their Derivatives

by Marco Farinone, Karolina Urbańska and Miłosz Pawlicki

Molecules 2020, 25(19), 4523; https://doi.org/10.3390/molecules25194523 - 2 Oct 2020

Cited by 16 | Viewed by 4014

Abstract

Molecular recognition is a specific non-covalent and frequently reversible interaction between two or more systems based on synthetically predefined character of the receptor. This phenomenon has been extensively studied over past few decades, being of particular interest to researchers due to its widespread occurrence in biological systems. In fact, a straightforward inspiration by biological systems present in living matter and based on, e.g., hydrogen bonding is easily noticeable in construction of molecular probes. A separate aspect also incorporated into the molecular recognition relies on the direct interaction between host and guest with a covalent bonding. To date, various artificial systems exhibiting molecular recognition and based on both types of interactions have been reported. Owing to their rich optoelectronic properties, chromophores constitute a broad and powerful class of receptors for a diverse range of substrates. This review focuses on BODIPY and porphyrin chromophores as probes for molecular recognition and chiral discrimination of amino acids and their derivatives. Full article

(This article belongs to the Special Issue Phthalocyanines and Porphyrins)

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