Asymmetrically bridged aroyl-S,N-ketene acetal-based multichromophores with aggregation-induced tunable emission

Abstract

Asymmetrically bridged aroyl-S,N-ketene acetals and aroyl-S,N-ketene acetal multichromophores can be readily synthesized in consecutive three-, four-, or five-component syntheses in good to excellent yields by several successive Suzuki-couplings of aroyl-S,N-ketene...

Solid‐State Emission and Aggregate Emission of Aroyl‐ S,N‐Ketene Acetals Are Controlled and Tuned by Their Substitution Pattern

“…As previously shown for related aroyl‐ S,N ‐ketene acetal AIEgens, ethanol/water mixtures turned out to be better suited for assessing the AIE properties in comparison to aqueous mixtures of other organic solvents, such as THF, acetonitrile, acetone [18–20] . Commencing with the aroyl moiety bearing substituent R 1 , the influence on both solid‐state emission and AIE behavior is tremendous as on the emission color.…”

“…As previously shown for related aroyl‐ S,N ‐ketene acetal AIEgens, ethanol/water mixtures turned out to be better suited for assessing the AIE properties in comparison to aqueous mixtures of other organic solvents, such as THF, acetonitrile, acetone. [ 18 , 19 , 20 ] Commencing with the aroyl moiety bearing substituent R 1 , the influence on both solid‐state emission and AIE behavior is tremendous as on the emission color. Methoxy and aliphatic groups on R 1 give rise to blue emission in the aggregated state ( λ em = 470–490 nm), halogenated derivatives luminesce blue‐greenish ( λ em = 500 nm) as well as most of the heterocyclic moieties, like thienyl or furyl substituted aroyl‐ S,N ‐ketene acetals.…”

“…After recently introducing aroyl‐ S,N ‐ketene acetals as a novel class of AIEgens, [18] we predominantly expanded the diversity‐oriented synthesis by concatenating Suzuki cross‐coupling to generate novel bi‐ [19] or multichromphores [20] for studying communication pathways between chromophores and for enabling energy transfer processes. Yet, in constituting the chromophores aroyl‐ S,N ‐ketene acetals per se revealed a pattern and correlations of the photophysical properties we now set out to nail down.…”

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

“…Phenyl and more complex dye systems were accepted as linker systems within the three-component Suzuki reaction. In order to synthesize the multichromophore systems, triborylated benzene and triphenylamine as well as tetraborylated tetraphenylethene were used as linkers (Supplementary Material S4) (Biesen et al, 2022).…”

Single molecule aggregation-induced dual and white-light emissive etherified aroyl-S,N-ketene acetalsviaone-pot synthesis

“…17 However, the synthesis of bi- or multichromophoric systems is often complex 18 and, as we have seen in previous works with bichromophoric emitters, it is not guaranteed that the dual emission is perfectly tuned for a white light emission to occur. 19 Therefore, single molecule white light emitters based on AIE properties rank high as relevant target structures. 1 e ,6 a ,20 Consequently, we returned from bi- and multichromophoric aroyl- S , N -ketene acetal systems to the core structural motif for a new approach to white light emitters.…”