Kinetic trapping of a cobalt(<scp>ii</scp>) metallocage using a carbazole-containing expanded carbaporphyrinoid ligand

Zhou, W.; Sarma, Tridib; Su, Yonghuan; Lei, Chuanhu; Sessler, Jonathan L.

doi:10.1039/d1sc06514a

Cited by 11 publications

(8 citation statements)

References 47 publications

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“…Appreciating that the connectivity of the carbazole moiety can affect its electronic properties, we prepared recently a meso -unsubstituted decaphyrin analogue V that incorporates 2,7-carbazolylene subunits. This system allows access to several conformational states without a substantive change in the electronic structure . We were thus keen to explore the chemistry of 3,6-carbazole-embedded porphyriniods.…”

Section: Introductionmentioning

confidence: 99%

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF₂ Complex

et al. 2022

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Carbazole precursors were used to prepare an octaphyrin. The conformation and electronic structure of the system could be modulated through trifluoroacetate (TFA) protonation and BF 2 complexation. The resulting nonaromatic macrocyclic complexes, 2-2TFA and 2-2BF 2 , displayed noteworthy photophysical properties. For instance, the diprotonated species 2-2TFA showed a strong panchromic absorption up to 800 nm, while the bis-BF 2 -chelated dipyrromethene (BODIPY)-like complex 2-2BF 2 exhibited an intense visible absorption feature (ε 535nm = 2.1 × 10 5 M −1 cm −1 ), as well as a relatively red-shifted emission at 640 nm characterized by a large Stokes shift. It was found that 2-2BF 2 could be used to construct a high-quality organic microlaser that functions under optical pumping. The present study highlights the potential utility of expanded porphyrins as possible laser dyes.

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Section: Introductionmentioning

confidence: 99%

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF₂ Complex

et al. 2022

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“…We postulated that carbazole-containing pyrrolic precursors, building blocks we have recently exploited to produce a carbadecaphyrin 37 and a cobalt( ii ) metallocage structure, 38 might allow construction of a 3D porphyrinoid containing co-planar dipyrrin units suitable for BF 2 complexation. The present study was undertaken as a test of this hypothesis.…”

Section: Resultsmentioning

confidence: 99%

Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays

et al. 2022

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“…Eventually, the intriguing molecular capsules have been recently reported, where the PAH‐embedded macrocycles served as structural facets to construct three‐dimensional cage architectures [54,85,86] …”

Section: Discussionmentioning

confidence: 99%

Phenanthrene‐Embedded Carbaporphyrinoids and Related Systems: From Ligands to Cages and Molecular Switches

Szyszko

2022

Eur J Org Chem

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This Review discusses the recent developments in the field of synthetic chemistry of PAH–porphyrin hybrids, emphasizing phenanthrene‐embedded carbaporphyrinoids and related systems. The discussion covers various aspects of phenanthriporphyrin and its derivates chemistry, including their spectroscopic features, aromaticity, core reactivity, and coordination properties. The development of expanded phenanthriporphyrinoids is outlined, followed by the presentation of related carbaporphyrinoids incorporating hydrocarbon moieties such as fluorene, biphenyl, terphenyl, and dibenzo[g,p]chrysene. The exploitation of phenanthriporphyrinoids as a unique class of ligands for organometallic chemistry is discussed, altogether with their use for the construction of conformational and stereochemical switches. The perspective for using related macrocycles as building blocks for carbaporphyrinoid cages is also outlined.

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Kinetic trapping of a cobalt(ii) metallocage using a carbazole-containing expanded carbaporphyrinoid ligand

Abstract: The meso-unsubstituted expanded porphyrinoid 3, incorporating two carbazole moieties, acts as an effective ligand for Co(II) and permits the isolation and X-ray diffraction-based characterization of a 6:3 metal-to-ligand metallocage complex...

Cited by 11 publications

References 47 publications

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF₂ Complex

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF₂ Complex

Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays

Phenanthrene‐Embedded Carbaporphyrinoids and Related Systems: From Ligands to Cages and Molecular Switches

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Kinetic trapping of a cobalt(ii) metallocage using a carbazole-containing expanded carbaporphyrinoid ligand

Abstract: The meso-unsubstituted expanded porphyrinoid 3, incorporating two carbazole moieties, acts as an effective ligand for Co(II) and permits the isolation and X-ray diffraction-based characterization of a 6:3 metal-to-ligand metallocage complex...

Cited by 11 publications

References 47 publications

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF2 Complex

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF2 Complex

Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays

Phenanthrene‐Embedded Carbaporphyrinoids and Related Systems: From Ligands to Cages and Molecular Switches

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Product

Resources

About

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF₂ Complex

3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF₂ Complex