Synthesis, structure, and host-guest chemistry of a pair of isomeric selenanthrene-bridged molecular cages

Lv, Wanqian; Song, Yadong; Lv, Xinyuan; Yuan, Jun; Zhu, Kelong

doi:10.1016/j.cclet.2023.108179

Cited by 2 publications

(2 citation statements)

References 41 publications

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“…In an attempt to shorten reaction times, 25 mol % triphenylphosphine was included as a phase-transfer catalyst (Table , entry 12); this unfortunately provided lower conversion than the standard conditions (entry 9); presumably the phosphine deactivates catalytically relevant species. Concomitant with our work, an article detailing the synthesis of a pair of isomeric selenanthrene-bridged molecular cages was published that utilizes analogous reaction conditions (DMA, K 2 CO 3 , 150 °C, 72 h) . This lends credence to the generality of the copper-catalyzed approach for preparing organoselenium compounds from aryl iodides and elemental selenium.…”

Section: Resultsmentioning

confidence: 75%

“…Concomitant with our work, an article detailing the synthesis of a pair of isomeric selenanthrene-bridged molecular cages was published that utilizes analogous reaction conditions (DMA, K 2 CO 3 , 150 °C, 72 h). 14 This lends credence to the generality of the copper-catalyzed approach for preparing organoselenium compounds from aryl iodides and elemental selenium.…”

Section: Resultsmentioning

confidence: 80%

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Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds

Larson,

Boyle,

Labrecque

et al. 2024

Inorg. Chem.

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The use of new dynamic scaffolds for constructing inorganic and organometallic complexes with enhanced reactivities is an important new research direction. Toward this fundamental aim, an improved synthesis of the dynamic scaffold selenanthrene, along with its monoxide, trans-dioxide and the previously unknown trioxide, is reported. A discussion of the potential reaction mechanism for selenanthrene is provided, and all products were characterized using 1 H, 13 C, and 77 Se nuclear magnetic resonance (NMR) spectroscopy and single-crystal X-ray crystallography. The dynamic ring inversion processes (i.e., "butterfly motion") for selenanthrene and its oxides were investigated using variabletemperature 1 H NMR and density functional theory calculations. The findings suggest that selenanthrene possesses a roughly equal barrier to inversion as its sulfur analogue, thianthrene. However, selenanthrene oxides evidently possess larger inversion barriers as compared to their sulfur analogues due to the enhanced electrostatic intramolecular interactions inherent between the highly polar selenium−oxygen bond and adjacent C−H moieties. Finally, we propose a quantitative "flexibility index" in deg/(kcal/mol) for various tricyclic scaffolds to provide researchers with a comparative scale of dynamic motion across many different systems.

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 80%

Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds

Larson,

Boyle,

Labrecque

et al. 2024

Inorg. Chem.

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Engineering Nanobelt Structure via Sulphur and Oxygen Doping: Synthesis, Structural Characterization, and Complexation with Fullerenes

Liu,

Wang,

Xie

et al. 2024

Chemistry An Asian Journal

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This study explores the synthesis, structural characterization, and host‐guest interactions of heteroatom bridged nanobelts, focusing on a cyclothianthrene nanobelt and a fused nanobelt incorporating thianthrene and phenoxathiin. Utilizing a cyclization‐followed‐by‐bridging synthetic approach, both molecular belts were successfully synthesized, and their structures confirmed through NMR and MALDI‐TOF‐MS analysis. Crystallographic studies revealed that the cyclothianthrene nanobelt adopts an octagonal column‐like conformation, while the hybrid belt forms an oval tub‐shaped shape, both exhibiting distinct assembly motifs. The host‐guest chemistry of these nanobelts was investigated with fullerenes (C60, C70, and PC61BM). The cyclothianthrene belt showed no interaction with these fullerenes, whereas the other belt demonstrated adaptive binding capabilities, forming stable complexes with C60 and C70 through π−π interactions and C‒H∙∙∙S hydrogen bonds. The binding constants indicated that the hybrid belt has a stronger affinity for C70 due to better size complementarity. Additionally, its interaction with PC61BM showcased a specific 1:1 binding mode despite exhibiting a smaller binding constant. This study underscores the impact of heteroatom incorporation on the structural and functional properties of nanobelts, offering insights for future molecular design strategies.

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Synthesis, structure, and host-guest chemistry of a pair of isomeric selenanthrene-bridged molecular cages

Cited by 2 publications

References 41 publications

Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds

Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds

Engineering Nanobelt Structure via Sulphur and Oxygen Doping: Synthesis, Structural Characterization, and Complexation with Fullerenes

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