9,10-Dibromoanthracene (original) (raw)
From Wikipedia, the free encyclopedia
9,10-Dibromoanthracene
Names | |
Preferred IUPAC name 9,10-Dibromoanthracene | |
Identifiers | |
CAS Number | 523-27-3 Y |
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/h1-8HKey: 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 |
Chemical compound
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]
Ian M. Heilbron and John S. Heaton were the first to synthesize this in 1923 in England.[1]
9,10-Dibromoanthracene is electroluminescent, giving off a blue light.[2]
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]
- ^ 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.