Synthesis, Characterization, and Fluorescence Properties of Two New Heterocyclic Compounds Containing 1,5-Dioxaspiro Group

Abstract

A precursor, C 21 H 29 NO 8 (A1) was prepared by reactions of 1,1-dimethoxy-N,Ndimethylmethanamine and 1,5-dioxaspiro[5.5]undecane-2,4-dione. The new N-containing heterocyclic compound, C 19 H 19 NO 4 (B1) was obtained by adding A1 into ethanol solution of o-toluidine. The crystal structure determination of two compounds were both found to belong to the triclinic P-1 space group. The precursor includes one (C 2 H 8 N) + cation and one (C 19 H 21 O 8 ) − anion, which constituted a chained structure by N-H···O intra-and intermolecular interactions. The title compound (B1) formed a 3D-network structure by weak C-H···O intermolecular interactions and π···π stacking interactions. The fluorescent behaviors of A1 and B1 in ethanol solution were discussed. The result shows that they exhibit blue and purplish blue emission, respectively.

Crystal Structure, Thermodynamic Properties and DFT Studies of 5,6-dimethyl-1H-benzo[d]imidazol-3-ium 3-((2,4-dioxo-1,5-dioxaspiro[5.5]undecan-3-ylidene)methyl) -2,4-dioxo-1,5-dioxaspiro[5.5]undecane Hydrate

“…The ν C-O bands of 1,3-dioxane ring were seen at 1261 cm −1 and 1225 cm −1 in DFT and at 1255 cm −1 and 1215 cm −1 in the IR spectra, respectively. These values agree well with literature reports [22][23][24]. The ν C=N and ν C-N vibrations occurred at 1490 cm −1 and 1347 cm −1 in DFT, respectively.…”

“…All kinds of spirocyclic compounds were designed and synthesized [19][20][21]. Based on the above reasons, our group has prepared several spirocyclic compounds derived from the 1,5-dioxaspiro group or the 6,10-dioxaspiro group in ten years [22][23][24][25]. However, to the best of our knowledge, among so many reported oxaspirocyclic compounds, neither theory studies nor comparison between the experimental and calculational results for derivatives from a benzodimidazole moiety are available.…”