Regioselektive Funktionalisierung von [2.2]Paracyclophanen: aktuelle Synthesefortschritte und Perspektiven

Hassan, Zahid; Spuling, Eduard; Knoll, Daniel M.; Bräse, Stefan

doi:10.1002/ange.201904863

Cited by 27 publications

(2 citation statements)

References 132 publications

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“…Beyond the prototypical double‐layered PCP, it remains to be explored whether this approach might be compatible with even larger molecular tectons [12] . For instance, co‐facially stacked PCP‐based multi‐layered molecules, ring‐fused or bridge‐extended cyclophane homologue systems could lead to new structural and functional attributes by constructing large, intricate, and highly ordered skeletally novel structures.…”

Section: Figurementioning

confidence: 99%

Stacking Cyclophanes into Chiral Microvessels

Hassan

Bräse

2023

Angew Chem Int Ed

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Engineering novel micro-/nanoscale systems and devices based on supramolecular assembly has tremendous potential from diverse applications perspective. However, controlling the size, shape, spatial arrangements, and hierarchical transcription by a dimensional organizing principle (1D-3D arrangement) without the help of templates remains a challenging task. In this vein, a recent study by Oki and colleagues reporting the stacking of chiral cyclophanes via intermolecular non-covalent interactions for crafting synchronous microcrystalline 3D chiral vessels with controlled conformational arrangements represents a truly remarkable illustration of molecular engineering. The microvessels bear stereocontrolled skeletal morphology, recognize stereoisomers and serve as containers to accommodate microcrystals, polymer particles, and fluorescent dyes. The full application scope of this fascinating research is far beyond non-covalent interactions, supramolecular self-assembly, and crystal engineering.

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Section: Figurementioning

confidence: 99%

Stacking Cyclophanes into Chiral Microvessels

Hassan

Bräse

2023

Angew Chem Int Ed

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“…[2.2]PC consists of two paraphenylenes bridged by a diethylene (–CH 2 CH 2 –) moiety and is widely employed as a building block for stacked π-conjugated structures. 19 20 The two phenylene units face each other and cannot rotate because of steric hindrance. Therefore, [2.2]PC with substituents at specific positions on the phenylene rings have planar chirality.…”

Section: Stereogenic Macrocycle Based On [22]paracyclophanementioning

confidence: 99%

Stereogenic π-Conjugated Macrocycles: Synthesis, Structure, and Chiroptical Properties Including Circularly Polarized Luminescence

Hasegawa,

Mazaki

2023

Synlett

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Highly symmetrical and aesthetically pleasing molecules have attracted the attention of organic chemists. We synthesized new highly symmetric stereogenic π-conjugated macrocycles with planar or axial chirality. Macrocyclic oligomers synthesized by Yamamoto coupling or Suzuki–Miyaura cross-coupling from the π-unit containing chirality. These cyclization reactions gave multiple oligomers in relatively high yields. We then elucidated their structures and investigated their chiroptical properties, including circular dichroism (CD) and circularly polarized luminescence (CPL). Because of the selection rule for rigid and symmetric structures, these macrocycles exhibit a high dissymmetry factor (g abs or g lum) for circularly polarized light in CD or CPL. Several rigid cyclic compounds retain a highly symmetric structure in the excited state and exhibit higher g lum values than common chiral organic compounds. This Account provides a brief background regarding chiroptical properties, followed by a summary of the various macrocycles synthesized in this study. We are glad if this Account will be a source of ideas not only for chemists working with π-conjugated compounds, but also for synthetic chemists working with chiral compounds, especially those engaged in asymmetric synthesis.1 Introduction2 Brief Description of Chiroptical Properties3 Stereogenic Macrocycle Based on [2.2]Paracyclophane3.1 Stereogenic Double-decker Oligothiophene3.2 Stereogenic Biselenophene Macrocycle3.3 Helical Oligophenylene Linked with [2.2]Paracyclophane4 Stereogenic Macrocycle Based on Binaphthyl4.1 Cyclic Oligomer of Chiral Binaphthyl4.2 Doubly Twisted Binaphthyl Dimer4.3 Cyclic Oligomer of Binaphthyl Extended with Paraphenylene4.4 Curved Helical Paraphenylene Anchoring Chiral Binaphthyl4.5 Binaphthyl-Hinged [5]-Helicene5 Summary

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Planar Chirality: A Mine for Catalysis and Structure Discovery

López

Palomo

2022

Angewandte Chemie

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Planar chirality is one of the most fascinating expressions of chirality, which is exploited by nature to lock three‐dimensional chiral conformations and, more recently, by chemists to create new chiral reagents, catalysts, and functional organic materials. Nevertheless, the shortage of procedures able to induce and secure asymmetry during the generation of these unique chiral entities has dissuaded chemists from exploiting their structural properties. This Minireview intends to illustrate the limited but remarkable catalytic methods that have been reported for the production of planar chirality in strained molecules and serve as a source of inspiration for the development of new unconventional procedures, which are expected to appear in the near future.

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Regioselektive Funktionalisierung von [2.2]Paracyclophanen: aktuelle Synthesefortschritte und Perspektiven

Cited by 27 publications

References 132 publications

Stacking Cyclophanes into Chiral Microvessels

Stacking Cyclophanes into Chiral Microvessels

Stereogenic π-Conjugated Macrocycles: Synthesis, Structure, and Chiroptical Properties Including Circularly Polarized Luminescence

Planar Chirality: A Mine for Catalysis and Structure Discovery

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