Paper
Synthesis and Otpical Properties of 2,7-Dibromo-4-amino-9H-fluorene
Published 2015 · Jiang Shan-sha
Chinese Journal of Synthetic Chemistry
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Abstract
2,7-Dibromo-4-amino-9H-fluorene( 4) was synthesized by bromination,nitration and reduction,using 9H-fluorene( 1) as the starting material. The structures were confirmed by1 H NMR,13 C NMR,IR and ESI-MS. Yield of bromination product,2,7-dibromo-9H-fluorene( 2),was 93. 8%under the optimum reaction conditions[CHCl3as the solvent and Cu Br2 as the catalyst,1 90 mmol,n( 1) ∶ n( Cu Br2) ∶ n( Br2) = 1. 0 ∶ 0. 025 ∶ 2. 89,at 0 ℃ for 24 h]. Yield of nitration product,2,7-dibromo-4-nitro-9H-fluorene( 3),was 94. 7% under optimum reaction conditions[85% HNO3+ 96%H2SO4as nitrating reagent,2 30 mmol,n( 2) ∶ n( HNO3) = 1. 0 ∶ 4. 6,at 70 ℃ for 1 h]. Yield of4 was 89. 5% under the optimum reaction conditions[Zn / Ca Cl2 as the reducing reagent,3 30 mmol,at reflux for 4 h]. The optical properties of 4 tests indecated that λmaxof 4 was 352. 4 nm,λemwere388. 4 nm and 412. 2 nm( λex352. 4 nm),the low optical band gap was 2. 66 e V.
2,7-Dibromo-4-amino-9H-fluorene(4) is a promising compound for synthesis of organic semiconductors and its optical properties.
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