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Issue 3, 2013
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One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

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Abstract

Carbohelicenes belong to a class of fascinating, chiral, and helicoidal molecules, which have a rich history in chemistry since the very beginning of the 20th century. A renewed interest in polyaromatic chemistry and new synthetic challenges toward the search for innovative physical, biological, chemical and opto-electronic properties have brought high motivation in this field of studies. Theoretical insights gained from polyaromatic, chiral, conjugated and distorted π-systems are also responsible for this development. Several synthetic avenues were originally reported for making lower helicenes, but for many years, photochemical synthesis has remained a major method for producing small amount of helicenes. High-dilution conditions is still a limiting factor in their synthesis. The fulgurous impact of organometallic chemistry, novel synthetic methods, and recent catalytic systems has promoted the development of helicene chemistry, toward a library of tailor-made and highly functionalized helicene molecules. Helicene chemistry is being considered as an expanding and modern field, leading to several applications in supramolecular chemistry, in nanosciences, in chemical-biology, in polymers and materials science. This first part of a series of three reviews on carbohelicenes will be devoted to a comprehensive report on non-stereoselective reactions and methods for producing helicenes, along with their functionalization.

Graphical abstract: One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

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Publication details

The article was received on 22 Apr 2012 and first published on 15 Nov 2012


Article type: Review Article
DOI: 10.1039/C2CS35154D
Citation: Chem. Soc. Rev., 2013,42, 968-1006
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    One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

    M. Gingras, Chem. Soc. Rev., 2013, 42, 968
    DOI: 10.1039/C2CS35154D

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