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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Conjugated Donor-Acceptor Macrocycles: Synthesis and Oxidation of ortho-Phenylene Bridged Cyclic
Zhihao Ma1, Shijun Gu1, Xiuqin Lu1
1State Key Laboratory of Advanced Fiber Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China.
Abstract:
Here, we reported the synthesis of an ortho-phenylene bridged cyclic tetra(benzo[c][1,2,5]thiadiazole) (3) by stepwise Suzuki-Miyaura couplings. Subsequent oxidation of 3 yielded a two-sided fused product 4, identified as an ortho-phenylene bridged cyclic triphenyleno[1,2-c:7,8-c']bis([1,2,5]thiadiazole) dimer. The structures of 3 and 4 were confirmed by high-resolution mass spectroscopies (HRMS) and NMR techniques. Their photophysical and electrochemical properties were fully characterized by ultraviolet-visible (UV-vis), fluorescence spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations.
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