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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
4-(3-Fluoro-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide
Abstract:
In the title compound, C(15)H(11)FN(4)OS, there are three independent mol-ecules, each with a disordered 3-fluoro-phenyl group [occupancy ratios = 0.547 (17):0.453 (17), 0.645 (5):0.355 (5) and 0.626 (15):0.374 (15)] and displaying dihedral angles of 4.2 (3), 25.2 (6) and 32.4 (5)° between the 2-oxoindoline and fluoro-substituted phenyl rings. Strong intra-molecular N-H⋯N and N-H⋯O and weak intra-molecular C-H⋯S hydrogen bonds complete S(5) and S(6) ring motifs, while strong inter-molecular N-H⋯O hydrogen bonds inter-connect the three independent mol-ecules through R(3) (3)(12) ring motifs. The three-mol-ecule units are in turn linked into polymeric sheets via C-H⋯F and C-H⋯S hydrogen bonds and π-π inter-actions [centroid-centroid distances in the range 3.520 (2)-3.820 (9) Å].
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