A highly efficient Rh(III)-catalyzed oxidative C−H/C−H cross-coupling of [1,2,4]triazolo[1,5-a]pyrimidines (TAP) with indoles and pyrroles has been developed, which provides an opportunity to rapidly assemble a large library of novel excited-state intramolecular proton transfer (ESIPT) fluorophores. The resulting 7-(pyrrol-2-yl)TAPs only show the enol-form emission, while 7-(indol-2-yl)TAPs would undergo an ESIPT process and mainly exhibit the keto-form emission. In highly polar solvents, the enol-form emission of 7-(indol-2-yl)TAPs is enhanced significantly, thus showing the dual emission of enol and keto forms.
Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes has been developed to construct extended π-conjugated ferrocenes with luminescent properties.
Disclosed herein is a highly efficient
one-pot synthetic strategy
to phenanthrone-type polyheterocycles via tandem rhodium(III)-catalyzed ortho-C–H heteroarylation of indolyl ketones and
copper(II)-promoted intramolecular cyclization. This protocol enables
a library of blue-emitting fluorophores with high quantum yields and
narrow full widths at half-maximum to be rapidly built from readily
available substrates, among of which 6,6,7,9,12-pentamethyl-6,12-dihydro-5H-benzofuro[2,3-a]carbazol-5-one (4a) exhibits pure blue emission with Commission Internationale
de I’Eclairage coordinates of (0.15, 0.09) and a high quantum
yield of 85% in CH2Cl2 solution.
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