Three-coordinate organoboron compounds BAr₂R (Ar = mesityl, R = 7-azaindolyl or 2,2'-dipyridylamino functionalized aryl or thienyl) for electroluminescent devices and supramolecular assembly

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  1. Get@NRC: Three-coordinate organoboron compounds BAr₂R (Ar = mesityl, R = 7-azaindolyl or 2,2'-dipyridylamino functionalized aryl or thienyl) for electroluminescent devices and supramolecular assembly (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1002/chem.200305579
AuthorSearch for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleChemistry: a European Journal
Volume10
Issue4
Pages9941006; # of pages: 13
Subjectblue emitter; boron; coordination chemistry; luminescence; N ligands; OLEDs
AbstractEight novel three-coordinate boron compounds with the general formula BAr2L, in which Ar is mesityl and L is a 7-azaindolyl- or a 2,2′-dipyridylamino-functionalized aryl or thienyl ligand, have been synthesized by Suzuki coupling, Ullmann condensation methods, or simple substitution reactions (L = p-(2,2′-dipyridylamino)phenyl, 1; p-(2,2′-dipyridylamino)biphenyl, 2; p-(7-azaindolyl)phenyl, 3; p-(7-azaindolyl)biphenyl, 4; 3,5-bis(2,2′-dipyridylamino)phenyl, 5; 3,5-bis(7-azaindolyl)phenyl, 6; p-[3,5-bis(2,2′-dipyridylamino)phenyl]phenyl, 7; 5-[p-(2,2′-dipyridylamino)phenyl]-2-thienyl, 8). The structures of 1, 3, and 5–7 have been determined by X-ray diffraction analyses. These new boron compounds are bright blue emitters. Electroluminescent devices using compound 2 or 8 as the emitter and the electron-transport layer have been successfully fabricated. Molecular orbital calculations (Gaussian 98) have established that the blue emission of compounds 1–8 originates from charge transfer between the π orbital of the ligand L and the pπ orbital of the boron center. The ability of these boron compounds to bind to metal centers to form supramolecular assemblies was demonstrated by treatment of compound 2 with Zn(O2CCF3)2, which generated a 1:1 chelate complex {2⋅Zn(O2CCF3)2} (10), and also by treatment of compound 4 with AgNO3, yielding a 2:1 coordination compound {(4)2⋅Ag(NO3)} (11). In the solid state, compounds 10 and 11 form interesting head-to-head and tail-to-tail extended structures that host solvent molecules such as benzene.
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AffiliationNational Research Council Canada; NRC Institute for Microstructural Sciences
Peer reviewedNo
NPARC number12744008
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Record identifier9271e901-69c1-41b4-8250-e9e3f3bd8995
Record created2009-10-27
Record modified2016-05-09
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