Conjugated Donor-Acceptor Macrocycles: Synthesis and Oxidation of -Phenylene Bridged Cyclic Tetra(benzo[][1,2,5]thiadiazole).

J Org Chem

State Key Laboratory of Advanced Fiber Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China.

Published: May 2025


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Article Abstract

Here, we reported the synthesis of an -phenylene bridged cyclic tetra(benzo[][1,2,5]thiadiazole) () by stepwise Suzuki-Miyaura couplings. Subsequent oxidation of yielded a two-sided fused product , identified as an -phenylene bridged cyclic triphenyleno[1,2-:7,8-']bis([1,2,5]thiadiazole) dimer. The structures of and 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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http://dx.doi.org/10.1021/acs.joc.5c00373DOI Listing

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