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2006年度最佳文章-化学类
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45_44/2006 “Sulflower”: A New Form of Carbon Sulfide

(Angew. Chem. Int. Ed. 2006, 45, 7367)

The bloom of a sunflower is used to describe the highly symmetric planar structure of octathio[8]circulene, whose trivial name “sulflower” derives from sulfur and flower (see cover picture). In their Communication on page 7367 ff., V. G. Nenajdenko and co-workers describe the synthesis and characterization of sulflower, a molecule that can be considered as a new form of carbon sulfide and as an oligothiophene, that is, as both inorganic and organic. (Background picture: “Sunflowers” by Vincent van Gogh. Copyright: Neue Pinakothek, Munich.)




Konstantin Yu. Chernichenko, Viktor V. Sumerin, Roman V. Shpanchenko, Dr., Elizabeth S. Balenkova, Prof. Dr., Valentine G. Nenajdenko, Prof. Dr. *
Department of Chemistry, Moscow State University, Leninskiye Gory, 119992 Moscow, Russia, Fax: (+7) 495-932-8846
email: Valentine G. Nenajdenko (nen@acylium.chem.msu.ru)


Dream Molecule:
 
Molecular formula: C
16S8
8-fold rotational symmetry

Chemistry is a chimera of science and art:

Left: Sunflowers by Vincent van Gogh (Copyright, Neue Pinakothek, Munich). Right: Types of annulated oligothiophenes: sulflower (1), linear 2, helical 3, and circulenic 4.

Oriented by theoretical calculation:

Calculated strain and geometries for fully thiophenic circulenes (n=number of thiophene rings). S yellow, C gray.

Concise and dream-like synthetical route:

Synthesis of circulene 1 from tetrathiophene 5 via polythiole 6 (n=1). Reagents and conditions: a) LDA (16 equiv), sulfur (16 equiv), room temperature, 24 h; b) aq. HCl; c) vacuum pyrolysis.

Unambiguous structural determination:


Packing of sulflower (1) molecules in the unit cell. S yellow, C white.


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