Order from Chaos: Self‐Assembly of Nanoprism from a Mixture of Tetratopic Terpyridine‐Porphyrin Conformers

Filosa, Alexander; Wang, Heng; Li, Weijian; Zhang, Wenjing; Ngo, Ellie; Piccolo, Jonathan E; Yang, Hai‐Bo; Li, Xiaopeng

doi:10.1002/cjoc.201900177

Cited by 11 publications

(6 citation statements)

References 47 publications

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“…The TWIM-MS spectrum also showed one set of signals with narrow distribution, suggesting the absence of other discernible structural or conformational isomers; such results also reflected the high backbone rigidity of the resulting assembly (Figure b). Collision cross-sections (CCSs) of each charge state, which can be calculated to reveal the size and shape of a charged species, ,, are summarized in Table S3. The averaged CCS is 2578.3 ± 49.6 Å 2 , agreeing well with the theoretical value of 2528.2 ± 34.0 Å 2 obtained from the modeling structure (Figure S94).…”

Section: Resultsmentioning

confidence: 99%

“…Specifically, a tridentate ligand, 2,6-di(1 H -imidazole-2-yl)pyridine (H 2 DAP), is incorporated into a tetratopic building block for precise assembly of three hexagonal wreaths upon complexation with Fe(II), Co(II), and Ni(II), instead of conventional tridentate moieties, e.g. , 2,2′:6′,2″-terpyridine (tpy), which are widely employed in the assembly of a large number of two-dimensional (2D) and three-dimensional (3D) supramolecular constructs. , The acidity of the N–H protons on the imidazole rings of H 2 DAP facilitates the state interconversion upon treatment with base and acid. Meanwhile, the ⟨H 2 DAP–Co(II)–H 2 DAP⟩ 2+ motif can undergo spontaneous oxidation upon alkali treatment in the air.…”

Section: Introductionmentioning

confidence: 99%

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Metallo-Supramolecular Hexagonal Wreath with Four Switchable States Based on a pH-Responsive Tridentate Ligand

Wei

Guo

et al. 2023

J. Am. Chem. Soc.

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In biological systems, many biomacromolecules (e.g., heme proteins) are capable of switching their states reversibly in response to external stimuli, endowing these natural architectures with a high level of diversity and functionality. Although tremendous efforts have been made to advance the complexity of artificial supramolecules, it remains a challenge to construct metallo-supramolecular systems that can carry out reversible interconversion among multiple states. Here, a pHresponsive tridentate ligand, 2,6-di(1H-imidazole-2-yl)pyridine (H 2 DAP), is incorporated into the multitopic building block for precise construction of giant metallo-supramolecular hexagonal wreaths with three metal ions, i.e., Fe(II), Co(II), and Ni(II), through coordination-driven self-assembly. In particular, a Co-linked wreath enables in situ reversible interconversion among four states in response to pH and oxidant/reductant with highly efficient conversion without losing structural integrity. During the state interconversion cycles, the physical properties of the assembled constructs are finely tuned, including the charge states of the backbone, valency of metal ions, and paramagnetic/diamagnetic features of complexes. Such discrete wreath structures with a charge-switchable backbone further facilitate layer-by-layer assembly of metallo-supramolecules on the substrate.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metallo-Supramolecular Hexagonal Wreath with Four Switchable States Based on a pH-Responsive Tridentate Ligand

Wei

Guo

et al. 2023

J. Am. Chem. Soc.

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“…Following this direction, a more recent example of 3D self‐assembled metallosupramolecular architectures using porphyrin‐linked tetratopic tpy ligands was reported by the Li group, where they constructed two discrete nanoprisms from similar tetratopic tpy‐based porphyrin building blocks. [ 82 ] Although the new porphyrin‐based tetratopic tpy ligands were detected with multiple conformations at ambient temperature by means of traveling‐wave ion mobility‐mass spectrometry (TWIM‐MS), [ 71 ] interestingly, self‐assembly of these ligands with Zn(II) produced discrete supramolecular nanoprisms rather than a mixture of polymer species. Probably, the observed nanoprisms were the energetically favorable structures so that all the ligands were fixed into one conformation.…”

Section: D Metallosupramolecular Architectures Based On Direct Self‐a...mentioning

confidence: 99%

Terpyridine‐Based 3D Discrete Metallosupramolecular Architectures

Guo

Chen

et al. 2022

Macromol. Rapid Commun.

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Terpyridine (tpy)‐based 3D discrete metallosupramolecular architectures, which are often inspired by polyhedral geometry and the biological structures found in nature, have drawn significant attention from the community of metallosupramolecular chemistry. Because of the linear tpy–M(II)–tpy connectivity, the creation of sophisticated 3D metallosupramolecules based on tpy remains a formidable synthetic challenge. Nevertheless, with recent advancement in ligand design and self‐assembly, diverse 3D metallosupramolecular polyhedrons, such as Platonic solids, Archimedean solids, prims as well as Johnson solids, have been constructed and their potential applications have been explored. This review summarizes the progress on tpy‐based discrete 3D metallosupramolecules, aiming to shed more light on the design and construction of novel discrete architectures with molecular‐level precision through coordination‐driven self‐assembly.

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“…Concerning L2, one synthetic strategy has been recently described. [31]. This product was synthesized in three steps from isophalaldehyde with an overall yield of almost 20% (Scheme 1 (c)).…”

Section: Figure 1: Terpyridinebenzaldehyde Derivatives L1 L2 and L3mentioning

confidence: 99%

Terpyridinebenzaldehyde isomers: One-pot facile synthesis

Jouaiti

2021

Synthetic Communications

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We have explored the use of (Diethoxymethyl)benzaldehyde readily available as a starting material allowing us to end up with Terpyridinebenzaldehyde isomers. An environmentally friendly procedure was undertaken for the synthesis of a series of 4, 3 and 2-([2,2 ′ :6 ′ ,2 ″terpyridin]-4 ′ -yl)benzaldehyde isomers (para, meta and ortho position). These compounds have been synthesized in one-pot conditions using ethanol and aqueous ammonia as solvents, at room temperature. This methodology offers substantial advantages with respect to its simplicity of operation, reaction time, satisfying yield of products and easy work-up procedure under mild reaction conditions. Apart from spectroscopic characterization, the structure of one of the Terpyridinebenzaldehyde derivative is confirmed by single-crystal X-ray diffraction.

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Order from Chaos: Self‐Assembly of Nanoprism from a Mixture of Tetratopic Terpyridine‐Porphyrin Conformers

Cited by 11 publications

References 47 publications

Metallo-Supramolecular Hexagonal Wreath with Four Switchable States Based on a pH-Responsive Tridentate Ligand

Metallo-Supramolecular Hexagonal Wreath with Four Switchable States Based on a pH-Responsive Tridentate Ligand

Terpyridine‐Based 3D Discrete Metallosupramolecular Architectures

Terpyridinebenzaldehyde isomers: One-pot facile synthesis

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