Sulflower

Short description: Chemical compound

Sulflower  |

Ball-and-stick model

Space-filling model

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Names
Preferred IUPAC name

1,12:3,4:6,7:9,10-Tetrasulfanocycloocta[1,2-c:3,4-c′:5,6-c′′:7,8-c′′′]tetrathiophene

Other names

Octathio[8]circulene

Identifiers

CAS Number

* 921210-36-8

3D model (JSmol)

* Interactive image

ChemSpider |

* 21267678

PubChem CID

* 101427667

CompTox Dashboard (EPA)

* DTXSID00891950

InChI

* InChI=1S/C16S8/c17-9-1-2-4-6-8-7-5-3(1)11(18-9)20-13(5)22-15(7)24-16(8)23-14(6)21-12(4)19-10(2)17

Key: SNTHAZVSUIFTDO-UHFFFAOYSA-N

SMILES

* c12c3c4c5c6c7c8c1c9sc2sc3sc4sc5sc6sc7sc8s9

Properties

Chemical formula

| C16S8
Molar mass | 448.66 g·mol−1
Appearance  | Dark red powder

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* PairSizeSet

Sulflower (a portmanteau of sulfur and sunflower) is a stable heterocyclic octacirculene based on thiophene. Sulflower does not contain any hydrogen. With molecular formula C16S8 the compound is considered a type of carbon sulfide. The molecule is flat and together with the 9-membered homolog is at a local strain energy minimum.[1]

Crystal structure  |

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Stacking of sulflower
molecules in the crystal structure | Packing of sulflower
molecules in the crystal structure

Its synthesis (a variation of the Ferrario reaction) is based on deprotonation of a tetrathiophene with lithium diisopropylamide followed by reaction with elemental sulfur to a sulfur-substituted intermediate followed by vacuum pyrolysis.

Sulflower synthesis

The sulflower molecule has a planar structure with D8h symmetry, i.e., all eight sulfur atoms as well as the two faces of the molecule are undistinguishable. Because of its planar structure, it is predicted to be able to store many hydrogen molecules between the stacks. The conformation of the H2 molecule is calculated to be "standing up" over the five membered rings. Detailed DFT calculations have been performed on these molecules.[2]

## References

1. ↑ Konstantin, Yu. Chernichenko; Sumerin, Viktor V.; Shpanchenko, Roman V.; Balenkova, Elizabeth S.; Nenajdenko, Valentine G. (2006). "Sulflower: A New Form of Carbon Sulfide". Angewandte Chemie International Edition 45 (44): 7367–7370. doi:10.1002/anie.200602190. PMID 17001717.
2. ↑ Datta, Ayan; Pati, Swapan K. (2007). "Computational design of high hydrogen adsorption efficiency in molecular "Sulflower"". J. Phys. Chem. C 111 (12): 4487. doi:10.1021/jp070609n.

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*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency