Synthesis, crystal structure and spectroscopic properties of a novel tricyclic cinnoline derivative

• DOI: 10.1016/j.dyepig.2017.02.038
• Publication Date: 2017-02-24T09:15:55Z
• Authors: Yuehua Yuan; Maozhong Tian; Qiangfeng Yin; Feng Feng
• Keywords: Cinnoline; Derivative (finance); Crystal (programming language); Tricyclic

Abstract A facile, efficient synthesis of the novel cinnoline derivative (E)-2,2′-(3-((3-bromophenyl) imino)-5-(tert-butyl)-3H-pyrrolo[3,2,1-ij]cinnoline-2,8-diyl)bis(propan-an-2-ol) (1) is reported. Richter cyclization of an o-ethynenearyldiazonium salt gave the cinnoline derivative which underwent a cyclization reaction to form the unexpected tricyclic compound 1. The absorption and fluorescence properties of cinnoline 1 were investigated in various solvents. A single crystal of 1 was grown and analyzed by X-ray diffraction analysis. The results showed that the inclusion compound was formed between the host (cinnoline 1) and the guest (acetone) in the crystal.