Fig. 3: Thermally controlled Diels–Alder reactions and dynamic behavior of charge-transfer complexes.
From: Topochemical synthesis of chiroptical materials through charge-transfer/Diels–Alder cascade reaction
A Incubation time-dependent 1H NMR spectra of compound 1 (50 mM) in the presence of 1 molar equiv. anthracene in CDCl3 at 80 °C. B Yields of DA adducts as functions of incubation time at 80 °C determined by 1H NMR. C, D Heating time-dependent absorption and emission (λex = 410 nm) spectra of compound 1 (0.5 mM) in the presence of 1 molar equiv. anthracene in DMSO at 120 °C. E HOMO-LUMO energy levels and distributions of different entities. Geometry optimizations were performed at the B3LYP-D3/def2-TZVP level. F ESP maps of 1 and anthracene. G Solid state diffusion reflectance spectra comparison of 1, CT complex (1:1) and DA adduct with anthracene. H Lifetime (τ) and quantum yields (Φ) of each DA adduct. I Thin films in polymethyl methacrylate (PMMA) on the glass substrates that show distinct emission under 365 nm illumination after CT and in situ DA addition reactions, which were utilized for smart display by heating.
