Stilbene-Based Molecular Switches with Aggregation Induced Emission (AIE) Function Constructed by Supramolecular Strategy

doi:10.6023/cjoc202210020

Abstract

Stilbene derivatives have been widely used for the construction of molecular switches having stimulus-response properties. Unlike the well-known tetraphenyl ethylene derivatives that have aggregation-induced emission (AIE) properties, it is a challenge to develop a stilbene molecular switch with AIE function. In this paper, a new type of stilbene molecular switch with AIE function was constructed by the supramolecular interaction of pillar[5]arene. This type of molecular switch has excellent thermal stability, and quantitative Z→E conversion can be achieved under acid catalysis. The light-driving reverse process achieved 87% of Z-configuration selectivity in the photostable state (PSS). The introduction of pillar[5]arene did not affect the switching performance of the parent compound. In a mixed solvent [tetrahydrofuran (THF)-H₂O], a stable aggregate was formed due to the supramolecular self-assembly of pillar[5]arene, which showed the AIE performance that the parent stilbene derivative did not possess. This supramolecular strategy opens a new window for building AIE-type molecular switches.

Key words: molecular switch, stilbene, pillar[5]arene, aggregation-induced emission

Cite this article

Ling Liu, Taotao Hao, Wanhua Wu, Cheng Yang. Stilbene-Based Molecular Switches with Aggregation Induced Emission (AIE) Function Constructed by Supramolecular Strategy[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2189-2196.

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Fig. & Tab. 5

Figure 1. Synthesis and 1H NMR characterization of norbornadiene-fused stilbene-based molecular switches (a) Synthetic route of the molecular switches; (b) 1Z; (c) 1Z in the presence of 0.5 equiv. of TFA; (d) 1E

Figure 2. (a) UV-vis spectra of 1E and 1Z (2.5×10–5 mol/L, DCM) and the changes of 1E upon irradiation at 341 nm for different periods; (b) CD spectra of the enantiomeric of 1Z and 1E (2.5×10–5 mol/L, DCM)

Figure 3. (a) Fluorescence spectra of 2Z (5×10–5 mol/L) in mixed solvents of THF/H2O; (b) plot of (I/I0) values of 2Z at 385 nm changes with the ratio of water content; (c) Fluorescence spectra of 1Z (5×10–5 mol/L) in mixed solvents of THF/H2O; (d) plot of (I/I0) values of 1Z at 425 nm changes with the ratio of water content (inset: a picture of 1Z in solid taken under 365 nm UV irradiation); (e) possible mechanism of 1Z self-assembly promoting AIE activity

Figure 4. (a) Photoluminescence spectra of 1Z (1×10–4 mol/L) in 90% aqueous solution (THF/H2O) upon irradiation at 310 nm for different periods; (b) Changes of fluorescence spectra of 1Z (1×10–4 mol/L, CHCl3) after adding different amounts of polycaprolactone (average molecular weight: 80000, 25 mg/mL chloroform) (inset: a picture of the gel composed of 200 mg polycaprolactone and 20 mg 1Z taken under 365 nm irradiation)

Scheme 1. Synthetic route of styryl bromide modified by ethoxy-pillar[5]arene

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利用超分子策略构筑具有聚集诱导发光(AIE)功能的二苯乙烯型分子开关