An Organic Molecular Nanobarrel that Hosts and Solubilizes C60 DOI Creative Commons
Saibal Bera, Satyajit Das, Manuel Melle‐Franco

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 135(5)

Published: Dec. 5, 2022

Abstract Organic cages have gained increasing attention in recent years as molecular hosts and porous materials. Among these, barrel‐shaped or nanobarrels are promising systems to encapsulate large they possess windows of the same size their internal cavity. However, these received little remain practically unexplored despite potential. Herein, we report design synthesis a new trigonal prismatic organic nanobarrel with two triangular diameter 12.7 Å optimal for encapsulation C 60 . Remarkably, this shows high affinity solvents which is virtually insoluble, providing stable solutions

Language: Английский

Recent advances in supramolecular fullerene chemistry DOI Creative Commons
Xingmao Chang, Youzhi Xu, Max von Delius

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(1), P. 47 - 83

Published: Oct. 18, 2023

We review recent work at the interface of supramolecular chemistry and fullerene chemistry. focus on selective functionalization, host–guest chemistry, non-covalent dyads, mechanically interlocked architectures 2D/3D assemblies.

Language: Английский

Citations

84
Modular synthesis, host–guest complexation and solvation-controlled relaxation of nanohoops with donor–acceptor structures DOI Creative Commons

Han Deng,

Zilong Guo,

Yaxin Wang

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(47), P. 14080 - 14089

Published: Jan. 1, 2022

A modular synthetic approach based on cyclocondensation reaction is introduced to produce nine nanohoops with tunable donor–acceptor structures.

Language: Английский

Citations

19
Subphthalocyanines: contracted porphyrinoids with expanded applications DOI Open Access
Jorge Labella, Tomás Torres⊗

Trends in Chemistry, Journal Year: 2023, Volume and Issue: 5(5), P. 353 - 366

Published: March 9, 2023

Language: Английский

Citations

13
An Organic Molecular Nanobarrel that Hosts and Solubilizes C60 DOI Creative Commons
Saibal Bera, Satyajit Das, Manuel Melle‐Franco

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(5)

Published: Dec. 5, 2022

Organic cages have gained increasing attention in recent years as molecular hosts and porous materials. Among these, barrel-shaped or nanobarrels are promising systems to encapsulate large they possess windows of the same size their internal cavity. However, these received little remain practically unexplored despite potential. Herein, we report design synthesis a new trigonal prismatic organic nanobarrel with two triangular diameter 12.7 Å optimal for encapsulation C60 . Remarkably, this shows high affinity solvents which is virtually insoluble, providing stable solutions

Language: Английский

Citations

16
Supramolecular Subphthalocyanine Cage as Catalytic Container for the Functionalization of Fullerenes in Water DOI Creative Commons
Ainhoa Salazar, Marta Moreno‐Simoni, Sunit Kumar

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(44)

Published: Sept. 11, 2023

Herein we report the first example of a supramolecular cage that works as catalytic molecular reactor to perform transformations over fullerenes in aqueous medium. Taking advantage ability metallo-organic Pd(II)-subphthalocyanine (SubPc) capsules form stable host:guest complexes with C60 , have prepared water-soluble provides hydrophobic environment for conducting cycloadditions encapsulated namely, Diels-Alder reactions anthracene. Indeed, presence amounts SubPc dissolved water promotes co-encapsulation insoluble and anthracene substrates, allowing reaction occur inside cavity under mild conditions. The lower stability complex resulting cycloadduct facilitates its displacement by pristine which grants turnover. Moreover, bis-addition compounds are regioselectively formed when using excess

Language: Английский

Citations

9
Acceleration of the Diels‐Alder Reaction between 9‐Functionalized Anthracenes and C60/C70 in the Cavity of a Water Soluble Subphthalocyanine Cage DOI Creative Commons
Ainhoa Salazar, Jorge Labella, Sunit Kumar

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 934 - 941

Published: Jan. 3, 2024

Abstract Herein we report on the acceleration of Diels‐Alder reaction between a series 9‐functionalized anthracenes and C 60 /C 70 encapsulated in water‐soluble metallo‐organic Pd(II)‐subphthalocyanine cage ( SubPc‐cage ), which performs as catalytic molecular reactor that provides beneficial hydrophobic environment. Negatively positively charged do not react either with or , due to favored solvation water medium and/or detrimental interactions positively‐charged Pd(II) corners . Experiments rendered parallel results, although proved more reactive, leading anthracene cycloadducts by α bonds. All results have been rationalized theoretical calculations at GFN2‐xTB level.

Language: Английский

Citations

3
First Subphthalocyanine Analogue with Fused 6H‐1,4‐diazepine Ring and its Conversion to Aminobenzamide Derivative DOI
Ivan A. Skvortsov,

Alexey E. Chufarin,

Mark V. Zaitsev

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(11)

Published: Sept. 28, 2023

Abstract Mixed cyclization of 5,7‐diphenyl‐6 H ‐1,4‐diazepine 2,3‐dicarbonitrile and tetrafluorophthalonitrile in the presence boron trichloride affords along with symmetrical perfluorinated subphthakocyanine, [F 12 s Pc], two novel subporphyrazine‐type products which were isolated by column chromatography characterized mass‐sprectometry, NMR, IR, UV‐VIS fluorescent spectroscopy. It was established that co‐cyclomerization dinitriles is accompanied electrophilic chlorination 1,4‐diazepine ring evolved Cl 2 resulting formation dibenzosubporphyrazine 8 Pc1] fused 6‐chloro‐5,7‐diphenyl‐6 fragment. According to DFT modelling 1 NMR data, a more stable diastereomer an axial atom formed no inversion observed. Hydrolytic cleavage fragment observed upon or strong acid (CF 3 COOH) leads 2‐amino‐3‐benzamide substituted dibenzo subporphyrazine Pc2]. Fluorescence (Φ F =0.03) ca 10 times lower than for Pc] =0.28) due combined effect intramolecular charge transfer (ICT) from donor diazepine acceptor Pc macrocycle heavy chlorine. Pc2] almost completely quenched ICT −NH group electron‐deficient core <0.001), but addition protonation amino switch‐ON fluorescence. Therefore, aminobenzamide subporphyrazines can be considered as perspective pH‐sensitive fluorophores.

Language: Английский

Citations

5
Fullerene-Functionalized Halogen-Bonding Heteroditopic Hosts for Ion-Pair Recognition DOI Creative Commons
Krzysztof M. Bąk, Igor Marques, Heike Kuhn

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(50), P. 27367 - 27379

Published: Dec. 7, 2023

Despite their hydrophobic surfaces with localized π-holes and rigid well-defined architectures providing a scaffold for preorganizing binding motifs, fullerenes remain unexplored as potential supramolecular host platforms the recognition of anions. Herein, we present first example rational design, synthesis, unique properties novel fullerene-functionalized halogen-bonding (XB) heteroditopic ion-pair receptors containing cation anion domains spatially separated by C60. Fullerene spatial separation XB donors crown ether complexed potassium resulted in rare an artificial receptor two sites opposing preferences hard soft halides. Importantly, incorporation C60 motif into structure has significant effect on halide selectivity, which is further amplified upon K+ binding. The fullerene-based exhibit enhanced selectivity polarizable iodide ion assisted potent XB-based domains, anion-π interactions, exceptional polarizability fullerene moiety, evidenced from DFT calculations. These observations serve to highlight proximal charged guest applications construction selective molecular sensors modulating solar cell devices.

Language: Английский

Citations

4
A chemiluminescent lantern: a coordination cage catalysed oxidation of luminol followed by chemiluminescence resonance energy-transfer DOI Creative Commons
Atena B. Şolea, Michael D. Ward

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(14), P. 4456 - 4461

Published: Jan. 1, 2023

A molecule of luminol bound as guest inside a Co8 coordination cage host undergoes oxidation by H2O2 to generate chemiluminescence process in which the Co(II) ions superstructure activate H2O2: accordingly not only co-locates reactants but also acts redox partner catalysis. The luminescence from cavity-bound can transfer its excitation energy surface-bound fluorescein molecules an unusual example Chemiluminescence Resonance Energy Transfer (CRET).

Language: Английский

Citations

3
Synthesis, Optical Properties, and Fluorescence Cell Imaging of Novel Mixed Fluorinated Subphthalocyanines DOI Creative Commons

Shutong Zhou,

Xiaojuan Lv, Minghui Li

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 725 - 725

Published: Jan. 11, 2023

Subphthalocyanines (SubPcs) are a kind of tripyrrolic macrocycle with boron atom at their core. Incorporating different units onto the SubPc periphery can endow them various unique properties. Herein, series novel fluorinated low-symmetry derivatives containing chlorine groups (F8-Cl4-SubPc, F4-Cl8-SubPc) and methoxy (F8-(OCH3)2-SubPc) were synthesized characterized by spectral methods (MS, FT-IR, 1H, 13C, 11B, 19F NMR spectroscopy), effect peripheral substituents on electronic structure was investigated cyclic voltammetry, theoretical calculation, absorption, emission spectroscopy. In contrast to perfluorinated SubPcs, these SubPcs revealed non-degenerate LUMO + 1 orbitals, especially F8-(OCH3)2-SubPc, which consistent split Q-band absorptions. The voltammetry that exhibited two or three reduction waves one oxidation wave, is reported SubPcs. Finally, an intracellular fluorescence imaging study compounds could enter cancer cells be entrapped in lysosomes, provides possibility future applications lysosome targeting.

Language: Английский

Citations

2