We put ammonia into an open-cage fullerene with a 20-membered ring ( 1) as the orifice and examined the properties of the complex using NMR and MALDI-TOF mass spectroscopy. The proton NMR shows a broad resonance corresponding to endohedral NH 3 at delta H = -12.3 ppm relative to TMS. This resonance was seen to narrow when a (14)N decoupling frequency was applied. MALDI spectroscopy confirmed the presence of both 1 ( m/ z = 1172) and 1 + NH 3 ( m/ z = 1189), and integrated intensities of MALDI peak trains and NMR resonances indicate an incorporation fraction of 35-50% under our experimental conditions. NMR observations showed a diminished incorporation fraction after 6 months of storage at -10 degrees C, which indicates that ammonia slowly escapes from the open-cage fullerene.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ja805579m | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C production.
Beilstein J Org Chem
February 2024
Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona (UdG), Girona 17003 Catalunya, Spain.
The regioselective functionalization of fullerenes holds significant promise for applications in the fields of medicinal chemistry, materials science, and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions between diynes and C as a novel procedure for generating C bis(fulleroid) derivatives. The aim is to shed light on the regioselectivity of the process through both experimental and computational approaches.
View Article and Find Full Text PDFAn open-cage bis[60]fulleroid as an electron transport material for tin halide perovskite solar cells.
Chem Commun (Camb)
February 2024
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
An open-cage bis[60]fulleroid (OC) was applied as an electron transport material (ETM) in tin (Sn) halide perovskite solar cells (PSCs). Due to the reduced offset between the energy levels of Sn-based perovskites and ETMs, the power conversion efficiency (PCE) of Sn-based PSCs with OC reached 9.6% with an open-circuit voltage () of 0.
View Article and Find Full Text PDFOpen-cage fullerenes as ligands for metals.
Dalton Trans
February 2024
Department of Chemistry, University of California, One Shields Avenue, Davis, CA, USA..
The remarkable structures of open-cage fullerenes with functionalization on the outer surface and an accessible inner void make them interesting ligands for reactions with metal complexes. The behaviors of open-cage fullerenes in reactions with various metal complexes are examined and compared to the corresponding reactions with intact fullerenes. The structural results from X-ray diffraction are emphasized.
View Article and Find Full Text PDFOpen-Cage Fullerene as a Macrocyclic Ligand for Na, Pt, and Rh Metal Complexes.
J Am Chem Soc
August 2023
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China.
An open-cage [60]fullerene derivative was prepared through Malaprade oxidation of a vicinal triol moiety as the key step. Above the 17-membered orifice, there is one carboxyl group. Three ketone carbonyl groups and one lactone carbonyl group are located on the rim of the orifice.
View Article and Find Full Text PDFTime-resolved imaging and analysis of the electron beam-induced formation of an open-cage metallo-azafullerene.
Nat Chem
October 2023
Department of Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo, Japan.
The visualization of single-molecule reactions provides crucial insights into chemical processes, and the ability to do so has grown with the advances in high-resolution transmission electron microscopy. There is currently a limited mechanistic understanding of chemical reactions under the electron beam. However, such reactions may enable synthetic methodologies that cannot be accessed by traditional organic chemistry methods.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!