Functional-group-regulated stimuli-responsive banana-shaped α-cyanostilbene derivatives: Dual-state emission, AIEE, acidochromism and their applications in anti-counterfeiting, fingerprint recognition and OLEDs

Zeng, Chongyang; Yang, Tianshun; Wang, Zengjia; Chen, Kai; Ge, Quanqian; Peng, Wenke; Zhang, Jinjing; Liu, Jialin; Zhang, Tao; Sun, Mei

doi:10.1016/j.jlumin.2024.120452

Cited by 6 publications

(1 citation statement)

References 49 publications

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“…Owing to the good fluorescence of TP 6- SA and TP 6- S in solid state, their performance in solid state lighting devices was investigated. The preparation of the LED device referred to refs − . First, the compound (20 mg) was mixed thoroughly with a silicone encapsulant (5 g, 1:1 weight ratio of silicone A to silicone B) in a small beaker.…”

Section: Resultsmentioning

confidence: 99%

Dual-State Fluorescence in Some Salicylaldehyde-triphenylene Discotic Liquid Crystal Derivatives Induced by Excited State Intramolecular Proton Transfer

Zeng,

Wang,

Wang

et al. 2024

Chem. Mater.

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A new family of excited state intramolecular proton transfer (ESIPT) molecules based on the enol/ketone tautomerism is reported. The molecules were designed to display columnar mesophases and consist of the archetypical 3,6,7,10,11-penta(alkoxy)triphenylene discotic core functionalized in the vacant "2-position" by a salicylaldehyde group (TPn-SA). For comparison and confirmation that the ESIPT effect is solely due to the salicylaldehyde group, structurally related triphenylene derivatives bearing benzaldehyde (TPn-S) or aldehyde (TPS6) side groups were also synthesized. These molecules were synthesized either by Suzuki−Miyaura cross-coupling (TPn-SA, TPn-S) or by the Bouveault aldehyde synthesis (Ar−Li and DMF, TPS6) in overall good yields. All triphenylene compounds show an enantiotropic columnar hexagonal mesophase over large temperature range. Furthermore, TPn-SA compounds undergo a mesophase to crystalline phase transformation upon UV light irradiation at 365 nm, caused by ESIPT-induced enol− ketone tautomerism. TP12-SA also self-assembles into room temperature gels in toluene and ethyl acetate at rather low critical gel concentration. TPn-SA and TPn-S present strong fluorescence in both solution and solid state, with fluorescence quantum yields for the TPn-SA compounds around ∼20%; TPS6, in contrast, does not show fluorescence in solid state because of aggregation-caused quenching. The dual emission observed for TPn-SA was supported by DFT calculation. The ketone emission is dominant in nonpolar solvents and aggregated states, while the enol emission is dominant in polar solvents or in dilute solutions. Finally, the performances of TP6-SA and TP6-S in solid-state lighting LED devices have been investigated.

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Section: Resultsmentioning

confidence: 99%

Dual-State Fluorescence in Some Salicylaldehyde-triphenylene Discotic Liquid Crystal Derivatives Induced by Excited State Intramolecular Proton Transfer

Zeng,

Wang,

Wang

et al. 2024

Chem. Mater.

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Photoswitchable AIE‐Active Supramolecular Self‐Assemblies for Biosensing and Bioimaging

Zhu,

Hou,

Wang

et al. 2024

Asian J Org Chem

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Photoswitchable fluorescent self‐assemblies exhibiting aggregation‐induced emission (AIE) properties have garnered widespread attention. Due to their great adaptiveness and responsiveness towards different wavelengths required by photoreaction, photo‐isomerization, and photoluminescence excitation, these fluorescent self‐assemblies show diverse emission behavior in a spatial, temporal, and polychromatic manner. Integrating organic photoswitches and AIE fluorophores, these photoluminescent nano‐assemblies has been proven to be an effective approach, allowing the development of sophisticated systems for drug release and cell regulation that can be precisely manipulated through light or other stimuli. This review systematically encapsulates recent advances in photoswitchable fluorescent self‐assemblies under multi‐scenario biological applications. The construction of photoswitchable AIE fluorophores through covalent and non‐covalent interactions and their multimodal regulation are detailed, along with their biological applications in biosensing, bioimaging, and drug therapy.

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Multifunctional electroluminescence materials with aggregation-induced emission properties and reversible mechanoluminescence

Fang,

Xu,

et al. 2025

Dyes and Pigments

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Functional-group-regulated stimuli-responsive banana-shaped α-cyanostilbene derivatives: Dual-state emission, AIEE, acidochromism and their applications in anti-counterfeiting, fingerprint recognition and OLEDs

Cited by 6 publications

References 49 publications

Dual-State Fluorescence in Some Salicylaldehyde-triphenylene Discotic Liquid Crystal Derivatives Induced by Excited State Intramolecular Proton Transfer

Dual-State Fluorescence in Some Salicylaldehyde-triphenylene Discotic Liquid Crystal Derivatives Induced by Excited State Intramolecular Proton Transfer

Photoswitchable AIE‐Active Supramolecular Self‐Assemblies for Biosensing and Bioimaging

Multifunctional electroluminescence materials with aggregation-induced emission properties and reversible mechanoluminescence

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