Synthesis of podands bearing aromatic end groups and complex formation with tropylium tetrafluoroborate in 1,2-dichloroethane

Lämsä, Markku; Raitamaa, Kirsi; Pursiainen, Jouni

doi:10.1002/(sici)1099-1395(199907)12:7<557::aid-poc155>3.0.co;2-t

Cited by 8 publications

(2 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pursiainen demonstrated the synthesis of podands bearing aromatic end groups and complex formation with tropylium tetrafluoroborate (1c) in 1,2-dichloroethane [ 94 ]. π–π stacking and cation–π interactions are important in the host–guest complexation of benzene-substituted crown ethers with electron-deficient aromatic carbenium ions such as tropylium and pyridinium.…”

Section: Complex Molecule Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Tropylium Ion, an Intriguing Moiety in Organic Chemistry

Zahra,

Saeed,

Mumtaz

et al. 2023

Molecules

View full text Add to dashboard Cite

The tropylium ion is a non-benzenoid aromatic species that works as a catalyst. This chemical entity brings about a large number of organic transformations, such as hydroboration reactions, ring contraction, the trapping of enolates, oxidative functionalization, metathesis, insertion, acetalization, and trans-acetalization reactions. The tropylium ion also functions as a coupling reagent in synthetic reactions. This cation’s versatility can be seen in its role in the synthesis of macrocyclic compounds and cage structures. Bearing a charge, the tropylium ion is more prone to nucleophilic/electrophilic reactions than neutral benzenoid equivalents. This ability enables it to assist in a variety of chemical reactions. The primary purpose of using tropylium ions in organic reactions is to replace transition metals in catalysis chemistry. It outperforms transition-metal catalysts in terms of its yield, moderate conditions, non-toxic byproducts, functional group tolerance, selectivity, and ease of handling. Furthermore, the tropylium ion is simple to synthesize in the laboratory. The current review incorporates the literature reported from 1950 to 2021; however, the last two decades have witnessed a phenomenal upsurge in the utilization of the tropylium ion in the facilitation of organic conversions. The importance of the tropylium ion as an environmentally safe catalyst in synthesis and a comprehensive summary of some important reactions catalyzed via tropylium cations are described.

show abstract

Section: Complex Molecule Synthesismentioning

confidence: 99%

“…Podands and their complexation ability have recently been used in supramolecular chemistry, most notably in the synthesis of rotaxanes and pseudorotaxanes. The study’s main goal was to find out how the macrocyclic effect, donor atoms, and aromatic substituents affected the complexation of aromatic cations [ 94 ].…”

Section: Complex Molecule Synthesismentioning

confidence: 99%

Tropylium Ion, an Intriguing Moiety in Organic Chemistry

Zahra,

Saeed,

Mumtaz

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

Molecular Tweezers

2018

Molecular Devices

View full text Add to dashboard Cite

Synthesis and characterization of new aromatic tweezers and complex formation with tropylium ion in 1,2‐dichloroethane

Lämsä

Kiviniemi

Kettukangas

et al. 2001

J of Physical Organic Chem

View full text Add to dashboard Cite

A series of benzene and pyridine tweezers bearing phenyl, naphthyl and anthryl receptor units was prepared and characterized. The x‐ray crystal structure of the 1,3‐bis(9‐methanolanthracene)methylbenzene ligand (5) is reported. UV–visible and NMR spectroscopy were used to investigate the host–guest chemistry of the new ligands in complexation with tropylium tetrafluoroborate as a model aromatic cationic guest in 1,2‐dichloroethane. The appearance of coloured charge‐transfer absorption bands demonstrates the complex formation with a tropylium ion. The enlargement of aryl receptor size from phenyl and naphthyl to anthryl increases the stability of complexes. Electron donor–acceptor interactions are an important driving force for complexation by molecular tweezers. The results are discussed and compared with those of previously studied systems containing crown ethers and podands. The bisanthracenes 5 and 1,3‐bis(9‐methanolanthracene)methylpyridine (6) are especially interesting in displaying both complexation ability and intramolecular cycloaddition via charge‐transfer excitation. Copyright © 2001 John Wiley & Sons, Ltd.

show abstract

Synthesis of podands bearing aromatic end groups and complex formation with tropylium tetrafluoroborate in 1,2-dichloroethane

Cited by 8 publications

References 22 publications

Tropylium Ion, an Intriguing Moiety in Organic Chemistry

Tropylium Ion, an Intriguing Moiety in Organic Chemistry

Molecular Tweezers

Synthesis and characterization of new aromatic tweezers and complex formation with tropylium ion in 1,2‐dichloroethane

Contact Info

Product

Resources

About