Helical Molecular Cages with sp-Conjugated Linkages
Wei Wu, Takahiro Kojima, Hiroshi Sakaguchi
Organics · pp. 2–2 · Published 25 Dec 2025
10.3390/org7010002Abstract
A conjugated helical cage, comprising two 1,3,5-tris(phenylethynyl)benzene units connected by diyne linkers, was successfully synthesized. X-ray crystallography revealed helical molecular structures with large twisted angles and a 1:1 mixture of P- and M-enantiomers. Variable-temperature-NMR measurement indicated the racemization process between the enantiomers occurs rapidly on the NMR timescale. The rapid interconversion is attributed to the flexible diyne linkages, even though they were believed to be rigid.
References (34)
- 1 Williams, 1997, A Comparison of the Lability of Mononu-clear Octahedral and Dinuclear Triple-Helical Complexes of Cobalt (II) [DOI]
- 2 Gliemann, 2021, A Chiral Molecular Cage Comprising Diethynylallenes and N-Heterotriangulenes for Enantioselective Recognition [DOI]
- 3 Beaudoin, 2017, Chiral Self-Sorting of [2 + 3] Salicylimine Cage Compounds [DOI]
- 4 Qiu, 2024, Highly stable sp2 carbon-conjugated porous organic cages [DOI]
- 5 Li, 2025, sp2 carbon conjugated covalent organic cage with efficient photocatalysis [DOI]
- 6 Chen, 2021, Self-Assembly of a Purely Covalent Cage with Homochirality by Imine Formation in Water [DOI]
- 7 Ren, 2016, Two-and Three-Tiered Stacked Architectures by Covalent Assembly [DOI]
- 8 Li, 2025, A Helical Tubular Dyad of [9]Cycloparaphenylene: Synthesis, Chiroptical Properties and Post-Functionalization [DOI]
- 9 Guo, 2025, Chiral covalent organic cages: Construction and chiral functions [DOI]
- 10 Mondal, 2016, Molecular cage impregnated palladium nanoparticles: Efficient, additive-free heterogeneous catalysts for cyanation of aryl halides [DOI]
- 11 Xue, 2024, Interplay of Stereochemistry and Charge Governs Guest Binding in Flexible ZnII4L4 Cages [DOI]
- 12 Pan, 2019, Chiral metal–organic cages/containers (MOCs): From structural and stereochemical design to applications [DOI]
- 13 Wang, 2025, Highly Conductive Chiral Organic Cages and Their Helical Assemblies Enable Efficient Spin Filtering [DOI]
- 14 Vanderkooy, 2019, Halogen bonding helicates encompassing iodonium cations [DOI]
- 15 Blatchly, 2003, Theoretical Study of Helix Formation in Substituted Phenylene Ethynylene Oligomers [DOI]
- 16 Hafezi, 2015, Modulating the Binding of Polycyclic Aromatic Hydrocarbons Insidea Hexacationic Cage by Anion-π Interactions [DOI]
- 17 Dale, 2014, Excage [DOI]
- 18 Wu, 2021, A contorted nanographene shelter [DOI]
- 19 Tuo, 2022, Naphthalene-pillaredbenzene triimide cage: An efficient receptor for polyhedral anions anda general tool for probing theoretically-existing anion-π bindingmotifs [DOI]
- 20 Zhu, 2022, A π-Electron Rich Cage via the Friedel-Crafts Reaction [DOI]
- 21 2022, Purely covalent molecular cages and containers for guest encapsulation [DOI]
- 22 Zhang, 2007, Synthesis and Structure of a Triptycene-Based Nanosized Molecular Cage [DOI]
- 23 Toyota, 2001, Effects of aryl and arylethynyl substituents at the 1-position on rotational barrier around C(sp)−C (sp3) bonds and bending deformation of acetylenic carbons in bis(9-triptycyl)ethynes [DOI]
- 24 Nobusue, 2012, Molecular propellers that consist of dehydrobenzo[14]annulene blades [DOI]
- 25 Sheldrick, 2008, A short history of SHELX [DOI]
- 26 Nobusue, 2025, Aryl Shift Rearrangement in Scholl-Type Reaction Toward Nanographene [DOI]
- 27 Huynh, 1988, A Short Route to Dehydro [12] Annulenes [DOI]
- 28 John, 1994, Synthesis of Polyphenylenes and Polynaphthalenes by Thermolysis of Enediynes and Dialkynylbenzenes [DOI]
- 29 Jacquemin, 2010, On the Performances of the M06 Family of Density Functionals for Electronic Excitation Energies [DOI]
- 30 Walker, 2013, Performance of M06, M06-2X, and M06-HF Density Functionals for conformationally Flexible Anionic Clusters: M06 Functionals Perform Better than B3LYP for a Model System with Dispersion and Ionic Hydrogen-Bonding Interactions [DOI]
- 31 Wang, 2024, Self-Similar Chiral Organic Molecular Cages [DOI]
- 32 2015, A Covalent Organic Helical Cage with Remarkable Chiroptical Amplification [DOI]
- 33 Okamoto, 2008, Chiral HPLC for efficient resolution of enantiomers [DOI]
- 34 Ikai, 2009, Structure Control of Polysaccharide Derivatives for Efficient Separation of Enantiomers by Chromatography [DOI]
Cited by 0
No indexed citations yet.
Related research
- A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
- Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
- Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
- Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
- Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage
Article metrics
Real usage data collected on this platform.
0
Page views
0
PDF downloads
0
Outbound clicks
0
Citations
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
No views recorded yet.
Traffic sources
Referring site, by host.
No traffic recorded yet.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.