Paper
Synthesis and Characterization of Photoactive Methyl 4-Bromo-3-((2,6-Difluorophenyl)diazenyl) Benzoate
Published Feb 9, 2021 · DOI · Eric D. Sylvester, J. Benedict
Journal of Chemical Crystallography
0
Citations
0
Influential Citations
Abstract
AbstractThe synthesis and structure of a novel ortho-fluoroazobenzene, methyl 4-bromo-3-((2,6-difluorophenyl)diazenyl) benzoate is described. The title molecule crystallizes in the centrocemetric space group P-1 with two rotomer molecules of the title compound in the asymmetric unit. The position of ortho-fluoro azo rings differ between the two rotomers with one molecule having a rotation angle of 4.4° and the other molecule having a rotation angle of 76.9° with respect to the methyl 4-bromobenzoate. Due to the tight packing the pure molecule was not seen to be photoactive. However, in solution the absorption bands in the visible region show a separation of about 20 nm as expected for o-fluoroazobenzene. A comparison to related and previously published co-crystals of substituted azobenzenes are presented.Graphic AbstractThe structure of a novel ortho-fluoroazobenzene, methyl 4-bromo-3-((2,6-difluorophenyl)diazenyl) benzoate reveals the presence of two crystallographically unique rotomers in the lattice, and although the molecule is photoactive in solution, the close-packed lattice appears to inhibit photo-induced structural reorganization in the crystalline state.
The novel ortho-fluoroazobenzene, methyl 4-bromo-3-((2,6-difluorophenyl)diazenyl) benzoate, is photoactive in solution but not in the crystalline state due to its close-packed lattice.
Full text analysis coming soon...