Coordination polymers with embedded recognition sites: lessons from cyclotriveratrylene-type ligands

Snelgrove, Matthew P.; Hardie, Michaele J.

doi:10.1039/d1ce00471a

Cited by 4 publications

(2 citation statements)

References 95 publications

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“…As methylene bridges can act as hinges, they have been used as important building blocks in the cyclization of planar aromatic units. − Owing to the broad applicability of methylene bridges, a variety of macrocyclic arenes, including calix[ n ]arenes, − calix[ n ]pyrrole, − cyclotriveratrylene, − and resorcin[ n ]arenes, − have been synthesized over recent decades. Compared with rigid and planar conjugated macrocycles, methylene-bridged macrocyclic arenes show conformational adaptability, which allows chirality recognition, − conformational response to guests, − and stimuli-responsive self-assembly. − Therefore, macrocyclic arenes can serve as interesting platforms in supramolecular chemistry.…”

Section: Introductionmentioning

confidence: 99%

Silapillar[n]arenes: Their Enhanced Electronic Conjugation and Conformational Versatility

Ohtani,

Akine,

Kato

et al. 2024

J. Am. Chem. Soc.

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During recent decades, methylene-bridged macrocyclic arenes have been widely used in supramolecular chemistry. However, their π-conjugations are very weak, as the methylene bridges disrupt the electronic communication between π orbitals of the aromatic units. Herein, we successfully synthesized a series of silapillar[n]arenes (n = 4, 6, and 8) using silylene bridging. These showed enhanced electronic conjugation compared with the parent pillar[n]arenes because of σ*−π* conjugation between σ* (Si−C) orbitals and π* orbitals of the benzenes. Owing to the longer Si−C bond compared with the C−C bond, silylene-bridging provides additional structural flexibility into the pillar[n]arene scaffolds; a strained silapillar[4]arene was formed, which is unavailable in the parent pillar[n]arenes because of the steric requirements. Furthermore, silapillar[n]arenes displayed interesting size-dependent structural and optical properties.

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Section: Introductionmentioning

confidence: 99%

Silapillar[n]arenes: Their Enhanced Electronic Conjugation and Conformational Versatility

Ohtani,

Akine,

Kato

et al. 2024

J. Am. Chem. Soc.

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“…Coordination polymers (CPs) − have received extensive attention due to their adjustable architectures and topologies − and potential applications in various fields, such as dye adsorption, − catalysis, − nuclide removal, − luminescence sensing, − and so forth. Compared with the rapidly increasing number of CPs based on transition metal and lanthanide nodes, − studies on actinide-involving CPs are relatively insufficient due to their intrinsic radioactivity and less availability.…”

Section: Introductionmentioning

confidence: 99%

Unveiling Structural Diversity of Uranyl Compounds of Aprotic 4,4′-Bipyridine N,N′-Dioxide Bearing O-Donors

et al. 2023

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As an aprotic O-donor ligand, 4,4′-bipyridine N,N′dioxide (DPO) shows good potential for the preparation of uranyl coordination compounds. In this work, by regulating reactant compositions and synthesis conditions, diverse coordination assembly between uranyl and DPO under different reaction conditions was achieved in the presence of other coexisting Odonors. A total of ten uranyl-DPO compounds, U-DPO-1 to U-DPO-10, have been synthesized by evaporation or hydro/ solvothermal treatment, and the possible competition and cooperation of DPO with other O-donors for the formation of these uranyl-DPO compounds are discussed. Starting with an aqueous solution of uranyl nitrate, it is found that an anionic nitrate or hydroxyl group is involved in the coordination sphere of uranyl in, and U-DPO-3 ((UO 2 )(DPO)(μ 2 -OH) 2 ), where DPO takes three different kinds of coordination modes, i.e. uncoordinated, monodentate, and biconnected. The utilization of UO 2 (CF 3 SO 3 ) 2 in acetonitrile, instead of an aqueous solution of uranyl nitrate, precludes the participation of nitrate and hydroxyl, and ensures the engagement of DPO ligands (4−5 DPO ligands for each uranyl) in a uranyl coordination sphere of U-DPO-4 ([(UO 2 )(CF 3 SO 3 )(DPO) 2 ](CF 3 SO 3 )), U-DPO-5 ([UO 2 (H 2 O)-(DPO) 2 ](CF 3 SO 3 ) 2 ) and U-DPO-6 ([(UO 2 )(DPO) 2.5 ](CF 3 SO 3 ) 2 ). Moreover, when combined with anionic carboxylate ligands, terephthalic acid (H 2 TPA), isophthalic acid (H 2 IPA), and succinic acid (H 2 SA), DPO works well with them to produce four mixedligand uranyl compounds with similar structures of two-dimensional (2D) networks or three-dimensional (3D) frameworks, U-DPO-7 ((UO 2 )(TPA)(DPO)), U-DPO-8 ((UO 2 ) 2 (DPO)(IPA) 2 •0.5H 2 O), U-DPO-9 ((UO 2 )(SA)(DPO)•H 2 O), and U-DPO-10 ((UO 2 ) 2 (μ 2 -OH)(SA) 1.5 (DPO)). Density functional theory (DFT) calculations conducted to probe the bonding features between uranyl ions and different O-donor ligands show that the bonding ability of DPO is better than that of anionic CF 3 SO 3 − , nitrate, and a neutral H 2 O molecule and comparable to that of an anionic carboxylate group. Characterization of physicochemical properties of U-DPO-7 and U-DPO-10 with high phase purity including infrared (IR) spectroscopy, thermogravimetric analysis (TGA), and luminescence properties is also provided.

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Synthetic progress of CTVs with different numbers of substituents on aromatic units

Li¹,

Chen

2022

Tetrahedron Letters

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Coordination polymers with embedded recognition sites: lessons from cyclotriveratrylene-type ligands

Abstract: Coordination polymers with molecular recognition sites are assembled using cyclotriveratrylene ligands. Many show differential guest-spaces with host and lattice sites available, however common host–guest and self-inclusion motifs can block sites.

Cited by 4 publications

References 95 publications

Silapillar[n]arenes: Their Enhanced Electronic Conjugation and Conformational Versatility

Silapillar[n]arenes: Their Enhanced Electronic Conjugation and Conformational Versatility

Unveiling Structural Diversity of Uranyl Compounds of Aprotic 4,4′-Bipyridine N,N′-Dioxide Bearing O-Donors

Synthetic progress of CTVs with different numbers of substituents on aromatic units

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