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Updated: Jun 1, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
(E)-1-[1-(6-Bromo-2-oxo-2H-chromen-3-yl)ethyl-idene]thio-semicarbazide
Abstract:
The title compound, C(12)H(10)BrN(3)O(2)S, exists in an E configuration with respect to the C=N bond. The approximately planar 2H-chromene ring system [maximum deviation = 0.059 (1) Å] is inclined at a dihedral angle of 17.50 (5)° with respect to the mean plane through the thio-semicarbazide unit and an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring. In the crystal structure, adjacent mol-ecules are linked by N-H⋯S hydrogen bonds, forming [010] chains built up from R(2) (2)(8) loops, such that each S atom accepts two such bonds. These chains are further inter-connected into sheets parallel to the ab plane via short Br⋯O inter-actions [3.0732 (13) Å] and a π-π aromatic stacking inter-action [3.7870 (8) Å] is also observed.
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