Enantioselective fullerene functionalization through stereochemical information transfer from a self-assembled cage

“…In nature, the coordination of metal ions with organic substrates has been exploited to create various functional compounds, such as chlorophyll, vitamin B 12 , hemoglobin, etc. Compared to other weak noncovalent interactions, coordination bonds are advantageous in terms of their directionality and predictability. − Inspired by nature, chemists have utilized coordination-driven self-assembly strategies to construct discrete architectures from two-dimensional (2D) rings to three-dimensional (3D) cages with precise sizes and shapes, − which have applications in areas such as catalysis, cancer treatment, and optical materials; , among these architectures, 2,2′:6′,2″-terpyridine (tpy) as a building block has gained widespread attention owing to its remarkable binding ability to different transition-metal ions. ,− Compared to 2D rings, 3D nanocages demonstrate promising applications for anion recognition, − C 60 encapsulation, − and controlled release − because of their regular configuration with fixed-size cavities that can selectively encapsulate guest molecules …”

Section: Introductionmentioning

confidence: 99%

Construction of 1,3,5-Triazine-Based Prisms and Their Enhanced Solid-State Emissions

et al. 2023

Inorg. Chem.

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In this study, two trigonal prisms based on the 1,3,5-triazine motif (SA and SB), distinguished by hydrophobic groups, were prepared by the self-assembly of tritopic terpyridine ligands and Zn(II) ions. SA and SB exhibited high luminescence efficiencies in the solid state, overcoming the fluorescence quenching of the 1,3,5-triazine group caused by π–π interactions. Notably, SA and SB exhibited different luminescence behaviors in the solution state and aggregation state. SB with 12 alkyl chains exhibited extremely weak fluorescence in a dilute solution, but its fluorescence intensity and photoluminescence quantum yield (PLQY) were significantly enhanced in the aggregated state (with the increase in the water fraction), especially in the solid state. Different from the gradually enhanced efficiency of SB, the PLQY of SA gradually decreased with the increase in aggregation but still maintained a high luminescence efficiency. These two complexes exhibited different modes to solve the fluorescence quenching of 1,3,5-triazine in the solid state. The hierarchical self-assembly of SB exhibited nanorods owing to the hydrophobic interactions of alky chains, while SA aggregated into spheres under the influence of π–π interactions.

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“…Angeregt durch die Beobachtung der überlegenen Leistung isomerenreiner Fulleren-Bis-Addukte in Solarzellen der dritten Generation [1] hat die chemo-, itero- [2] regio-und stereoselektive [3] Mehrfachfunktionalisierung von Fullerenen in den letzten zehn Jahren eine Renaissance erlebt. [4] Der klassische Ansatz zur Lösung des Regioselektivitätsproblems der Bis-Addition wurde von Diederich [5] entwickelt und beruht auf der Verwendung von bifunktionellen Tether.…”

Section: Introductionunclassified

Synthese von C₆₀/[10]CPP‐Catenanen durch Regioselektive Nanokapsel‐Templierte Bingel Bis‐Addition

Steudel,

Ubasart,

Leanza

et al. 2023

Angewandte Chemie

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Die Addition von zwei unsymmetrischen Malonsäureestern an das Buckminster‐Fulleren C60 kann zu 22 spektroskopisch unterscheidbaren isomeren Produkten führen und stellt daher eine beachtliche synthetische Herausforderung dar. In dieser Arbeit erreichen wir eine Selektivität von 87 % für die Bildung eines einzigen (in,out‐trans‐3)‐Isomers, indem wir drei Methoden kombinieren: (i) wir verwenden ein Ausgangsmaterial, in dem die beiden Malonsäureester kovalent verbunden sind (Tether); (ii) wir bilden den starken supramolekularen Komplex von C60 mit dem formstabilen [10]CPP‐Makrozyklus (Nanohoop‐Template) und (iii) wir schlossen diesen Komplex weiter in eine selbstorganisierte Nanokapsel ein (Schattenmaske). Die Variation der Alkylkette zeigte die Limitationen der Methode auf und die Ringdynamik in den ungewöhnlichen [2]Catenanen wurde in silico mit atomistischer Auflösung untersucht. Diese Arbeit erweitert das Spektrum der mechanisch ineinandergreifenden Architekturen mit Cycloparaphenylen (CPP) erheblich.

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Enantioselective fullerene functionalization through stereochemical information transfer from a self-assembled cage

Cited by 60 publications

References 53 publications

Superior thermoelectric properties of bulk and monolayer fullerene networks

Superior thermoelectric properties of bulk and monolayer fullerene networks

Construction of 1,3,5-Triazine-Based Prisms and Their Enhanced Solid-State Emissions

Synthese von C₆₀/[10]CPP‐Catenanen durch Regioselektive Nanokapsel‐Templierte Bingel Bis‐Addition

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Enantioselective fullerene functionalization through stereochemical information transfer from a self-assembled cage

Cited by 60 publications

References 53 publications

Superior thermoelectric properties of bulk and monolayer fullerene networks

Superior thermoelectric properties of bulk and monolayer fullerene networks

Construction of 1,3,5-Triazine-Based Prisms and Their Enhanced Solid-State Emissions

Synthese von C60/[10]CPP‐Catenanen durch Regioselektive Nanokapsel‐Templierte Bingel Bis‐Addition

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Synthese von C₆₀/[10]CPP‐Catenanen durch Regioselektive Nanokapsel‐Templierte Bingel Bis‐Addition