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Search for "porphyrins" in Full Text gives 55 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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  • homometallic (Zn/Zn) and heterometallic (Zn/Au) compounds. In the open state, the porphyrins do not interact and the closing process allows the system to acquire distinct properties depending on the porphyrin. For the Zn/Zn system, guest binding abilities have been observed with diamines that can coordinate
  • arms. In the uncoordinated state, the conformation is not fixed so the porphyrins do not interact but when the tweezers are closed the porphyrins are facing each other and can interact. The closed and open states exhibit different electrochemical and photochemical properties. The porphyrin interaction
  • in the closed state splits the second oxidation of the porphyrins from a two-electron process to two single-electron processes. This is due to the electrostatic repulsion between the two positively charged complexes that shift the second oxidation potential. The absorption bands of the closed state
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Published 01 Mar 2024
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  • ][42][43][44][45][46], azulenes and their homologous compounds [32][47][48][49][50][51][52][53][54][55][56][57][58], boron dipyrromethenes (BODIPYs) [41][59][60][61], porphyrins [62][63][64], chlorophylls [65][66], triazenes [67][68], ynamides [69][70][71], arylynamines [72], indoles [73], and γ
  • CS-state formation for 60 depending on the solvent, was also observed for excitation at 458 nm corresponding to the ICT band. A series of multicomponent systems consisting of anilino-substituted TCBD or PCBD coupled with zinc porphyrins (ZnPs) were synthesized, and their photophysical properties were
  • that the introduction of the TCBD structures switched the role of porphyrins in photoevents (Figure 12) [150]. In molecules 105, 106, 109, and 110 without the TCBD structure, when the metalloporphyrin moiety (MP) was subjected to Soret-band excitation (426 nm) in benzonitrile, the emergence of the S2
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Published 22 Jan 2024

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

  • Julika Schlosser,
  • Olga Fedorova,
  • Yuri Fedorov and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

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  • turn oxidizes the DNA bases [46]. As a result, various classes of photosensitizers [47][48][49] have been established, for example, porphyrins [50], chlorins [51], phthalocyanines [52], porphycenes [53], metal-organic complexes [54][55][56], dye aggregates [57], as well as nano-drug carriers and metal
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Published 18 Jan 2024

Substituent-controlled construction of A4B2-hexaphyrins and A3B-porphyrins: a mechanistic evaluation

  • Seda Cinar,
  • Dilek Isik Tasgin and
  • Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

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  • , Central Campus, 06790 Etimesgut, Ankara, Turkey 10.3762/bjoc.19.135 Abstract A substituent-dependent construction of novel A3B-porphyrins along with A4B2-hexaphyrins was realized by the reactions of N-tosylimines and meso-aryl-substituted tripyrranes in the presence of Cu(OTf)2 as the catalyst. The
  • of porphyrinogen and hexaphyrinogen forms. Keywords: A4B2-hexaphyrin; A3B-porphyrin; N-tosylimine; Cu(OTf)2 catalysis; HRESI–TOF analysis; Introduction Porphyrins and expanded porphyrins have found widespread applications in supramolecular chemistry [1][2][3][4]. Expanded porphyrins are utilized as
  • building blocks in the fields of near-infrared (NIR) dyes [5], nonlinear optical (NLO) materials [2], and photosensitizers in photodynamic therapy [1], however, their synthesis is still a challenge for chemists. Hexaphyrins are one of the most investigated structures among expanded porphyrins owing to
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Published 06 Dec 2023

Selectivity control towards CO versus H2 for photo-driven CO2 reduction with a novel Co(II) catalyst

  • Lisa-Lou Gracia,
  • Philip Henkel,
  • Olaf Fuhr and
  • Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

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  • advantages for tailoring new catalysts to specific reactions and optimize selectivity [22][27]. Cobalt catalysts successfully employed in CO2 reduction are mainly based on macrocyclic ligands, such as tetraazacyclodecene and its derivatives [3][28][29], porphyrins [30][31][32][33][34], or phthalocyanines [35
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Published 17 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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  • Maksym Matviyishyn Bartosz Szyszko Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland 10.3762/bjoc.19.120 Abstract Porphyrins and crown ether hybrids have emerged as a promising class of molecules composed of elements of a tetrapyrrole macrocycle and an
  • oligo(ethylene glycol) segment. These hybrid systems constitute a broad group of compounds, including crowned porphyrins, crownphyrins, and calixpyrrole-crown ether systems forming Pacman complexes with transition metals. Their unique nature accustoms them as excellent ligands and hosts capable of
  • materials science [10]. These two classes of molecules seem particularly remarkable among the endless family of macrocyclic compounds due to their unique features and easy accessibility. The popularity of porphyrins and crown ethers has been so extensive that the whole range of these macrocycles is even
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Published 27 Oct 2023

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

  • Chandra Sekhar Tekuri,
  • Pargat Singh and
  • Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

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  • ) porphyrins were transformed to the corresponding free base and zinc(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins under standard demetallation and zinc insertion conditions. The absorption and emission properties of the obtained porphyrins were investigated by using UV–visible and fluorescence
  • spectroscopy. The preliminary photophysical results revealed a significant red-shift in their absorption and emission spectra as compared to the meso-tetrakis(4-methylphenyl)porphyrins due to the extended π-conjugation. Keywords: bathochromic shift; benzo[f]chromeno[2,3-h]quinoxalinoporphyrins; catalysis
  • aldehydes and dimedone in chloroform at 65 °C. The optical properties of the newly prepared porphyrins have been investigated by using UV–vis and emission spectroscopy and the results are presented in this paper. Results and Discussion Synthesis The required precursors, copper(II) 2,3-diamino-5,10,15,20
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Published 11 Aug 2023

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

  • Dileep Kumar Singh and
  • Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

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  • , vitamin B12, porphyrins, chlorins, and bacteriochlorins also contain pyrroles rings (Figure 1). For the synthesis of pyrrole derivatives, many classic methods have been used, including Knorr pyrrole synthesis [29][30], Paal–Knorr synthesis [31][32][33], Hantzsch pyrrole synthesis [34][35][36], Clauson
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Published 27 Jun 2023

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

  • Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

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  • ; Introduction Porphyrins are an aromatic, immensely conjugated, and colorful macrocyclic array with remarkable optical, electrochemical, and biological features. It is one of the most fascinating heterocyclic molecules which have various applications in catalysis, materials sciences, photochemistry and
  • majority of porphyrin hybrids are synthesized by modifying β- and meso-positions of porphyrin, thus numerous chromophoric groups and biologically important scaffolds have been attached to porphyrins at these positions in recent years. In the past, many synthetic procedures have been utilized to covalently
  • includes a brief synthetic procedure with reaction conditions, product yields, and photophysical and other properties of the end products. Review Overview of CuAAC click reactions on porphyrins The CuAAC-inspired click reaction is particularly useful for the coupling of two different moieties comprising
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Published 22 Mar 2023

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole

  • Baris Temelli and
  • Pinar Kapci

Beilstein J. Org. Chem. 2022, 18, 1403–1409, doi:10.3762/bjoc.18.145

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  • porphyrins, are tetrapyrrolic aromatic compounds, with the lack of one meso-carbon atom on the macrocycle [1][2][3][4]. This feature supplies a smaller ring cavity than in the case of porphyrins, three NH in the core, and coordination ability with high-valence transition metal ions. It is noteworthy that
  • studies on porphyrins, which have many application areas such as photodynamic therapy and photovoltaic systems, have focused on oligomeric and polymeric structures in the last two decades [5][6][7][8][9]. Although such porphyrin structures have been used successfully in the development of molecular
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Published 06 Oct 2022

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

  • Jamshid Amiri Moghaddam,
  • Huijuan Guo,
  • Karsten Willing,
  • Thomas Wichard and
  • Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

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  • -2-naphthoic acid (DHNA) via an intermediate decarboxylative coupling step yielding demethylmenaquinone (DMK) [9]. In contrast, COX10 and chlorophyll synthases are known to fuse prenyl or phytyl tails to porphyrins as acceptors, while homogentisate prenyltransferases catalyze the condensation of
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Published 22 Jun 2022

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

  • Prodip Howlader and
  • Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

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  • . Accordingly, the distinct zinc porphyrins 55 and 57 were positioned at a defined distance through two NDABCO → ZnPor interactions. Clearly, without additional measures, homo- and heteromeric assemblies would form. However, due to the additional HETPYP interaction(s) in the presence of copper(I) ions
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Published 27 May 2022
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  • medicinally active as well as smart functional materials possessing the pyrrole as a fundamental subunit [28][29][30]. Additionally, 3,4-disubstituted pyrrole derivatives are versatile building blocks for the production of diverse bioactive molecules like co-enzyme, alkaloids, porphyrins and other related
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Published 02 Jun 2021

Structural effects of meso-halogenation on porphyrins

  • Keith J. Flanagan,
  • Maximilian Paradiz Dominguez,
  • Zoi Melissari,
  • Hans-Georg Eckhardt,
  • René M. Williams,
  • Dáire Gibbons,
  • Caroline Prior,
  • Gemma M. Locke,
  • Alina Meindl,
  • Aoife A. Ryan and
  • Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

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  • has been a topic of strong interest over the past decades. With this in mind we have characterized a series of direct meso-halogenated porphyrins using single crystal X-ray crystallography. This is accompanied by a detailed conformational analysis of all deposited meso-halogenated porphyrins in the
  • . Additionally, we have used density functional theory calculations to determine the structure of several halogenated porphyrins. This contrasts conformational analysis with existing X-ray structures and gives a method to characterize samples that are difficult to crystallize. By using the methods outlined above
  • we were able to deduce the impact a meso halogen has on a porphyrin, for example, meso-halogenation is dependent on the type of alternate substituents present when forming supramolecular assemblies. Furthermore, we have designed a method to predict the conformation of halogenated porphyrins, without
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Published 14 May 2021

Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

  • Jannis Ludwig,
  • Tobias Moje,
  • Fynn Röhricht and
  • Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2589–2597, doi:10.3762/bjoc.16.210

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  • Jannis Ludwig Tobias Moje Fynn Rohricht Rainer Herges Otto Diels Institute of Organic Chemistry, University of Kiel, Otto-Hahn-Platz 3–4, 24098 Kiel, Germany 10.3762/bjoc.16.210 Abstract We present the synthesis and the spin switching efficiencies of Ni(II)-porphyrins substituted with
  • )-porphyrins; photoswitch; record player molecules; spin state; spin switch; Introduction Molecular spin switches operated with visible light in homogeneous solution [1] or on surfaces [2], hold promise for a number of hitherto unprecedented applications such as switchable contrast agents [3][4][5][6][7
  • state. 4-Substituted pyridines exhibit a distinguished correlation between basicity and coordination strength as axial ligands with Ni-porphyrins [12]. Hence, Hammet σ values might be used to predict and to systematically optimize the performance of the spin switch. In previous studies we have shown
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Published 21 Oct 2020

NMR Spectroscopy of supramolecular chemistry on protein surfaces

  • Peter Bayer,
  • Anja Matena and
  • Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

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  • ], guanidiniocarbonylpyrrole (GCP) ligands [41][42][43][44][45][46], cucurbiturils [47][48][49][50][51], porphyrins [52][53][54][55][56][57][58][59][60], metal complexes [61][62][63], foldamers [64][65][66][67], nanoparticles [34][68], imprinted polymers [69][70][71][72], and dendrimers [73][74]. In this review, we focus
  • Survivin – Histone H3 interaction by a GCP ligand has been shown to inhibit tumor proliferation in cell culture [46]. Porphyrins, either with or without a complexed metal ion in the center, have been used as planar hydrophobic scaffolds where either negatively charged carboxylate or positively charged
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Published 09 Oct 2020

Azo-dimethylaminopyridine-functionalized Ni(II)-porphyrin as a photoswitchable nucleophilic catalyst

  • Jannis Ludwig,
  • Julian Helberg,
  • Hendrik Zipse and
  • Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2119–2126, doi:10.3762/bjoc.16.179

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  • activity. The rate constants in the two switching states differ by a factor of 2.2, and the catalytic switching is reversible. Keywords: catalysis; Ni(II)-porphyrins; nucleophilic catalyst; photoswitch; record player molecules; spin switch; Introduction Photoswitchable catalysis has been realized
  • very strong ligand with respect to axial coordination to Ni-porphyrins [25]. According to 1H NMR studies, however, the trans isomer exhibits concentration-dependent coordination, which clearly indicates intermolecular coordination. Again, this is due to the very strong coordination power of the DMAP
  • ligand. At a total concentration of 4 mM of the Ni-porphyrin, after irradiation with 435 nm (THF-d8, 25 °C) 46% of the molecules are in cis and 54% are in trans configuration. Whereas the cis isomers are almost completely coordinated, the trans porphyrins still exhibit 7% coordination, which is due to a
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Published 31 Aug 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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  • porphyrin colour from a purple powder to green when immobilised. The immobilisation of porphyrins onto polystyrene supports has been reported prior to this through covalent and electrostatic attractions but often suffered from poor coupling yields and low loadings [133][134][135][136]. Similarly, ionic
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Published 26 Jun 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

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  • renewal of porphyrin applications in photocatalysis. Finally, the reaction scale in which the methodologies were developed are highlighted since this is an important parameter in the authors’ opinion. Keywords: energy transfer; photocatalysis; photooxygenation; photoredox; porphyrins; Introduction In
  • detoxification of anthropogenic chemicals (cytochrome P450) and oxygen transport (hemoglobin) [5][6]. Taking into account this big group of molecules, porphyrins are notable due to both their physicochemical and electronic properties, which can be fine-tuned by functionalization of the core structures [8]. The
  • adequate tuning of the porphyrin properties can enable them to absorb light in almost all of the UV–vis spectral range. Porphyrins also have elevated molar absorptivity (ca 105 L·mol−1·cm−1) and appropriate electronic levels for both energy transfer (ET) and single electron transfer (SET) in many
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Published 06 May 2020

Towards triptycene functionalization and triptycene-linked porphyrin arrays

  • Gemma M. Locke,
  • Keith J. Flanagan and
  • Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

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  • investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes
  • evident linearity in these systems. Moreover, initial UV–vis and fluorescence studies show the promise of triptycene as a linker for electron transfer studies, showcasing its isolating nature. Keywords: BODIPY; Pd-catalyzed cross-coupling; porphyrins; Sonogashira cross-coupling; triptycene; Introduction
  • and electrochemical properties of the porphyrins by increasing the size of the aromatic π-system [16]. In contrast, our approach described herein deviates significantly from previous studies by examining how isolating the individual porphyrin units affects the overall photophysical properties of the
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Published 17 Apr 2020

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

  • Valentina A. Ol’shevskaya,
  • Elena G. Kononova and
  • Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

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  • Valentina A. Ol'shevskaya Elena G. Kononova Andrei V. Zaitsev A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991, Vavilova St. 28, Moscow, Russian Federation 10.3762/bjoc.15.263 Abstract Maleimide-containing fluorinated porphyrins and chlorins were
  • ; porphyrin; spectral characteristics; synthesis; Introduction Porphyrins belong to a broad class of the natural and synthetic macroheterocyclic compounds with unique properties. They play an important role in photosynthesis [1], catalysis [2][3], nonlinear optics [4][5], polymer synthesis [6] and energy
  • conversions [7]. Porphyrins have been extensively studied as potential photosensitizers in a photodynamic therapy (PDT) [8][9], a promising treatment modality for several cancer and infectious diseases. In PDT, light, O2, and a photosensitizing drug are combined to produce a selective therapeutic effect via
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Published 13 Nov 2019

α-Photooxygenation of chiral aldehydes with singlet oxygen

  • Dominika J. Walaszek,
  • Magdalena Jawiczuk,
  • Jakub Durka,
  • Olga Drapała and
  • Dorota Gryko

Beilstein J. Org. Chem. 2019, 15, 2076–2084, doi:10.3762/bjoc.15.205

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  • dichroism (ECD) and TD-DFT methods. Keywords: 1,2-diols; ECD; enamines; organocatalysis; porphyrins; silyl ethers of diarylprolinols; singlet oxygen; Introduction Carbonyl compounds are one of the most important building blocks in organic synthesis. As a consequence, there is a constant need for new
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Published 30 Aug 2019

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

  • Silvie Rimpelová,
  • Michal Jurášek,
  • Lucie Peterková,
  • Jiří Bejček,
  • Vojtěch Spiwok,
  • Miloš Majdl,
  • Michal Jirásko,
  • Miloš Buděšínský,
  • Juraj Harmatha,
  • Eva Kmoníčková,
  • Pavel Drašar and
  • Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

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  • ] and was also found to be cytotoxic with localization to the endoplasmic reticulum [8]. The cytotoxicity of compound 2 prompted the preparation and evaluation of compound 2 conjugates with porphyrins [9] and steroids [10] for targeted uptake of compound 2 into cancer cells, and the conjugates showed
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Published 13 Aug 2019

Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

  • Xiujun Liu,
  • Xiang Ma and
  • Yaqing Feng

Beilstein J. Org. Chem. 2019, 15, 1434–1440, doi:10.3762/bjoc.15.143

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  • Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China 10.3762/bjoc.15.143 Abstract Isoxazoline-linked porphyrins have been synthesized by a regioselective 1,3-dipolar cycloaddition reaction between vinylporphyrin 2 and nitrile oxides. The steric interaction directed the
  • reaction trajectory, in which only the product with a link between the 5-position of the isoxazoline and the β-position of porphyrin was observed. The isoxazoline-porphyrins 3a,b have been characterized by absorption, emission, 1H NMR and mass spectra. Later, the crystal structure of 3a was obtained and
  • the double bond after the cycloaddition reaction, the absorption spectrum shifted to shorter wavelengths. The isoxazoline-modified porphyrins have been identified by absorption, emission, 1H NMR and mass spectrometry, and 3a was further characterized by X-ray analysis. In the crystal, a pair of
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Published 28 Jun 2019

Extending mechanochemical porphyrin synthesis to bulkier aromatics: tetramesitylporphyrin

  • Qiwen Su and
  • Tamara D. Hamilton

Beilstein J. Org. Chem. 2019, 15, 1149–1153, doi:10.3762/bjoc.15.111

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  • -positions have been historically difficult in porphyrin synthesis, presumably owing to steric hindrance around the reactive site. We have used mechanochemistry for the simple, room-temperature synthesis of tetra-meso-substituted porphyrins. In the present study, mesitaldehyde undergoes acid-catalyzed
  • , simple, room-temperature method for producing tetra-meso-substituted porphyrins with bulky substituents. Keywords: condensation; grinding; mechanochemistry; milling; porphyrin; sterically-hindered; Introduction Porphyrins and related macrocycles such as chlorins, corroles, and bacteriochlorins carry
  • out important functions in nature including light harvesting (i.e., chlorophyll), oxygen transport (i.e., heme), biocatalysis, and electron transfer. The ability to synthesize porphyrins bearing a variety of chemical and steric functionalities on the periphery is important in fields as diverse as
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Published 22 May 2019
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