9,10-Dibromoanthracene

9,10-Dibromoanthracene
Names
	Preferred IUPAC name 9,10-Dibromoanthracene
Identifiers
CAS Number	523-27-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3183379;
ChemSpider	61529;
ECHA InfoCard	100.007.586
EC Number	208-342-4;
PubChem CID	68226;
UNII	61CP7C5Y82;
CompTox Dashboard (EPA)	DTXSID5049312;
	InChI InChI=1S/C14H8Br2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H Key: BRUOAURMAFDGLP-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2Br)Br;
Properties
Chemical formula	C14H8Br2
Molar mass	336.026 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H410
Precautionary statements	P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

9,10-Dibromoanthracene is an organic chemical compound containing anthracene with two bromine atoms substituted on its central ring. It is notable in that it was the first single molecule to have a chemical reaction observed by an atomic force microscope and scanning tunneling microscopy.^[1]

Production

Ian M. Heilbron and John S. Heaton were the first to synthesize this in 1923 in England.^[1]

Properties

9,10-Dibromoanthracene is electroluminescent, giving off a blue light.^[2]

Reactions

The carbon–bromine bonds can be fragmented in two successive steps by voltage pulses from tip of a scanning tunneling microscope. The resulting carbon radicals are stabilized by the sodium chloride substrate on which the 9,10-dibromoanthracene reactant was placed. Further voltage pulses cause the diradical to convert to a diyne (or back again) via a Bergman cyclization reaction.^[3]

References

^ ^a ^b "9,10-Dibromoanthracene". American Chemical Society.
^ Brar, Sukhwinder Singh; Mahajan, Aman; Bedi, R. K. (10 January 2014). "Structural, optical and electrical characterization of hot wall grown 9,10-dibromoanthracene films for light emitting applications". Electronic Materials Letters. 10 (1): 199–204. doi:10.1007/s13391-013-3153-8. S2CID 135788635.
^ Borman, Stu (2016). "Chemists Nudge Molecule To React Then Watch Bonds Break And Form". Vol. 94, no. 5. p. 7.

[motw-1] "9,10-Dibromoanthracene". American Chemical Society.

[2] Brar, Sukhwinder Singh; Mahajan, Aman; Bedi, R. K. (10 January 2014). "Structural, optical and electrical characterization of hot wall grown 9,10-dibromoanthracene films for light emitting applications". Electronic Materials Letters. 10 (1): 199–204. doi:10.1007/s13391-013-3153-8. S2CID 135788635.

[3] Borman, Stu (2016). "Chemists Nudge Molecule To React Then Watch Bonds Break And Form". Vol. 94, no. 5. p. 7.

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