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A Synthetic Strategy for Cofacial Porphyrin-Based Homo- and Heterobimetallic Complexes.

ABSTRACT: We present a straightforward and generally applicable synthesis route for cofacially linked homo- and heterobimetallic porphyrin complexes. The protocol allows the synthesis of unsymmetrical aryl-based meso-meso as well as ?-meso-linked porphyrins. Our method significantly increases the overall yield for the published compound known as o-phenylene-bisporphyrin (OBBP) by a factor of 6.8. Besides the synthesis of 16 novel homobimetallic complexes containing Mn^III , Fe^III , Ni^II , Cu^II , Zn^II , and Pd^II , we achieved the first single-crystal X-ray structure of an unsymmetrical cofacial benzene-linked porphyrin dimer containing both planar-chiral enantiomers of a Ni^II ₂ complex. Additionally, this new methodology allows access to heterobimetallic complexes such as the Fe^III -Ni^II containing carbon monoxide dehydrogenase active site analogue. The isolated species were investigated by various techniques, including ion mobility spectrometry, DFT calculations, and UV/Vis spectroscopy. This allowed us to probe the influence of interplane distance on Soret band splitting.

SUBMITTER: Schissler C

PROVIDER: S-EPMC7898677 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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A Synthetic Strategy for Cofacial Porphyrin-Based Homo- and Heterobimetallic Complexes.

Schissler Christoph C Schneider Erik K EK Felker Benjamin B Weis Patrick P Nieger Martin M Kappes Manfred M MM Bräse Stefan S

Chemistry (Weinheim an der Bergstrasse, Germany) 20210118 9

We present a straightforward and generally applicable synthesis route for cofacially linked homo- and heterobimetallic porphyrin complexes. The protocol allows the synthesis of unsymmetrical aryl-based meso-meso as well as β-meso-linked porphyrins. Our method significantly increases the overall yield for the published compound known as o-phenylene-bisporphyrin (OBBP) by a factor of 6.8. Besides the synthesis of 16 novel homobimetallic complexes containing Mn<sup>III</sup> , Fe<sup>III</sup> , Ni ...[more]

PMID: 33459421

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Project description:A heterobimetallic complex, (TPFC)Sn-Co(TAP) (TPFC = 5,10,15-tris(pentafluorophenyl)corrole, TAP = 5,10,15,20-tetrakis(p-methoxyphenyl)porphyrin), was synthesized. The complex featured a Sn-Co bond with a bond dissociation enthalpy (BDE) of 30.2 ± 0.9 kcal mol-1 and a bond dissociation Gibbs free energy (BDFE) of 21.0 ± 0.2 kcal mol-1, which underwent homolysis to produce the (TPFC)Sn radical and (TAP)CoII under either heat or visible light irradiation. The novel tin radical (TPFC)Sn, being the first four-coordinate tin radical observed at room temperature, was studied spectroscopically and computationally. (TPFC)Sn-Co(TAP) promoted the oligomerization of aryl alkynes to give the insertion products (TPFC)Sn-(CH 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 C(Ar)) n -Co(TAP) (n = 1, 2, or 3) as well as 1,3,5-triarylbenzenes. Mechanistic studies revealed a radical chain mechanism involving the (TPFC)Sn radical as the key intermediate.

Dataset Information

A Synthetic Strategy for Cofacial Porphyrin-Based Homo- and Heterobimetallic Complexes.

Publications

A Synthetic Strategy for Cofacial Porphyrin-Based Homo- and Heterobimetallic Complexes.

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