Synthesis of Functionalized Six-Membered-Ring Azahelicenes. 2022

Francesca Fontana, and Benedetta Bertolotti
Dipartimento di Ingegneria e Scienze Applicate, Università di Bergamo, 24044 Dalmine, Italy.

Functionalization, namely the introduction of side groups onto the molecular scaffold of a helicene, may have either the purpose of modifying the electronic properties of the parent helicene, e.g., by adding electron-withdrawing or electron-donating groups, or the scope of providing the helicene with a "handle", which can be reacted to bind the molecule to another molecule or to a solid structure, such as a carbon or metal surface, or again to allow for complexation of the helicene with metal ions. The possible approaches are two-fold: the synthesis of the helicene can be performed using starting materials that already contain a side group, or the side group can be introduced after the synthesis of the parent helicene. As azahelicenes are helicenes bearing one or more nitrogen atom(s) in the molecular framework, parent azahelicenes can be functionalized on carbon atoms by exploiting the presence of the electron-withdrawing nitrogen atom. Moreover, they can be transformed into quaternary salts, whose properties are quite different from those of the parent azahelicenes in terms of the solubility and electronic properties. This review aims to provide a survey of the different synthetic methods available to attain this fascinating class of compounds.

UI MeSH Term Description Entries
D009584 Nitrogen An element with the atomic symbol N, atomic number 7, and atomic weight [14.00643; 14.00728]. Nitrogen exists as a diatomic gas and makes up about 78% of the earth's atmosphere by volume. It is a constituent of proteins and nucleic acids and found in all living cells.
D002244 Carbon A nonmetallic element with atomic symbol C, atomic number 6, and atomic weight [12.0096; 12.0116]. It may occur as several different allotropes including DIAMOND; CHARCOAL; and GRAPHITE; and as SOOT from incompletely burned fuel. Carbon-12,Vitreous Carbon,Carbon 12,Carbon, Vitreous
D004583 Electrons Stable elementary particles having the smallest known negative charge, present in all elements; also called negatrons. Positively charged electrons are called positrons. The numbers, energies and arrangement of electrons around atomic nuclei determine the chemical identities of elements. Beams of electrons are called CATHODE RAYS. Fast Electrons,Negatrons,Positrons,Electron,Electron, Fast,Electrons, Fast,Fast Electron,Negatron,Positron
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Francesca Fontana, and Benedetta Bertolotti
July 2018, Chemical communications (Cambridge, England),
Francesca Fontana, and Benedetta Bertolotti
March 2024, Organic & biomolecular chemistry,
Francesca Fontana, and Benedetta Bertolotti
January 2016, Beilstein journal of organic chemistry,
Francesca Fontana, and Benedetta Bertolotti
July 2004, The Journal of organic chemistry,
Francesca Fontana, and Benedetta Bertolotti
September 2010, Chemistry (Weinheim an der Bergstrasse, Germany),
Francesca Fontana, and Benedetta Bertolotti
September 2022, Molecules (Basel, Switzerland),
Francesca Fontana, and Benedetta Bertolotti
August 1975, Prostaglandins,
Francesca Fontana, and Benedetta Bertolotti
January 2021, National science review,
Copied contents to your clipboard!