Structural investigation of 5,10-A2B2-type porphyrins: palladium(II) and zinc(II) complexes of 5,10-dibromo-15,20-bis(4-methylphenyl)porphyrin

Senge, Ma­thias O.; Zawadzka, Monika

doi:10.1107/s2053229614023687

Cited by 4 publications

(4 citation statements)

References 15 publications

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“…The structure of 40a (not shown, see Figure S6 in the Supporting Information) exhibits a relatively planar scaffold on which the 3,5‐di‐ tert ‐butylphenyl groups are oriented orthogonal to the plane of the 24‐atom ring. Its structural features are similar to those of other A 2 B 2 porphyrins (with B = Br) . The C a –C m (Br)–C a angle [128.6(2)°] is similar to those previously reported (127.9–128.9°).…”

Section: Resultssupporting

confidence: 83%

Comparative Synthetic Strategies for the Generation of 5,10‐ and 5,15‐Substituted Push‐Pull Porphyrins

et al. 2017

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Contemporary applications in optics, medicine, solar cells, or material science are increasingly reliant on unsymmetrically substituted porphyrins. Due to their widespread applications and rise in demand we undertook a comparative analysis of synthetic strategies for meso‐substituted porphyrins and present the synthesis of five different series of so‐called A2BC push‐pull porphyrins. The synthetic pathways used were applied to both 5,15‐substituted and 5,10‐substituted porphyrins, showcasing their flexibility and adaptability for different needs. Our approach combines well‐known reactions with a strategic and logical stepwise functionalization allowing researchers to change and modify the electronic properties of these systems at various points of the syntheses. This facilitates the easy optimization of the synthesis of systems of current interest, for example, porphyrins for dye‐sensitized solar cells (DSSCs) or for use in nonlinear optics, as well as fast generation of compound libraries.

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Section: Resultssupporting

confidence: 83%

Comparative Synthetic Strategies for the Generation of 5,10‐ and 5,15‐Substituted Push‐Pull Porphyrins

et al. 2017

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“…The hydrogen•••halogen interactions are listed in Table 2. Compounds 16-18 are a series of structures that only differ by the type of metal center in the porphyrin core [34,35]. In compound 16 the stacked porphyrin layers are orientated in a parallel arrangement with a 3.704(4) Å separation (Figure 20A) whilst a lateral alignment where the bromine atoms are pointing towards the tolyl groups in a linear network is observed (Figure 20B).…”

Section: 10-di-halo-substituted Porphyrinsmentioning

confidence: 99%

“…Details on the refinement of NESHUO (2) [27], UDERUR (3) [22], NOGWEN (12) [23], HUMWES (13A) [24], HUMWAO ( 14) [24], LASMOK (15) [33], RAKGAN (16) [34], ZOXQUA (17) [35], ZOXCAS (18) [35], BASDOR (19) [36], YISZAD(20) [39], QUGMEM (21) [38], QUGMIQ ( 22) [38], and MORBEC (23) [37] were previously reported.…”

Section: Previous Structuresmentioning

confidence: 99%

Structural effects of meso-halogenation on porphyrins

Flanagan

Dominguez

Melissari

et al. 2021

Beilstein J. Org. Chem.

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The use of halogens in the crystal engineering of supramolecular porphyrin assemblies 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 CSD. In this study we have used the Hirshfeld fingerprint plots together with normal-coordinate structural decomposition and determined crystal structures to elucidate the conformation, present intermolecular interactions, and compare respective contacts within the crystalline architectures. 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 need of crystallization, using DFT calculations with a high degree of accuracy.

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“…We speculate that this is due to a change in symmetry of the porphyrin. Palladium usually sits co-planar in the porphyrin, 33,37,38 but when in solid the symmetry may change due to distortion of the porphyrin molecule which could be due to the polymerization step or the different subtituents in the meso positions.…”

Section: Synthesis and Characterisation Of The Hydrogelsmentioning

confidence: 99%

Synthesis and bactericidal properties of porphyrins immobilized in a polyacrylamide support: influence of metal complexation on photoactivity

et al. 2017

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Structural investigation of 5,10-A₂B₂-type porphyrins: palladium(II) and zinc(II) complexes of 5,10-dibromo-15,20-bis(4-methylphenyl)porphyrin

Cited by 4 publications

References 15 publications

Comparative Synthetic Strategies for the Generation of 5,10‐ and 5,15‐Substituted Push‐Pull Porphyrins

Comparative Synthetic Strategies for the Generation of 5,10‐ and 5,15‐Substituted Push‐Pull Porphyrins

Structural effects of meso-halogenation on porphyrins

Synthesis and bactericidal properties of porphyrins immobilized in a polyacrylamide support: influence of metal complexation on photoactivity

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