Tetraphenylethene-based macrocycles with dual-ring topology: synthesis, structures, and applications

Zhang, Junying; Kang, Wenbing; Xu, Xing-Dong

doi:10.1039/d3qo01426f

Cited by 12 publications

(3 citation statements)

References 83 publications

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“…Through a facile three-step process, TPE units were embedded into crown ether to synthesize TPE-cored butterfly-shaped macrocycles (Figure 2). Our methodology distinguishes itself from previous reports on crown ether-functionalized TPE-based macrocycles obtained by the direct intermolecular cyclization, [21][22][23] as it is challenging to achieve high yields of smaller-sized crown ether ringfunctionalized TPE-macrocycles due to the strain resulting from intramolecular cyclization. The reaction of diketone compound with zinc powder (5 equiv.)…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 93%

Unprecedented TPE-Embedded Butterfly Bis-Crown Ether with Controllable Conformation and Supramolecular Chiroptical Property

Hu,

Tian,

Zuo

et al. 2024

Preprint

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Understanding how subtle structural differences between macrocyclic conformational isomers impact their properties and separation has garnered increasing attention in the field of supramolecular synthetic chemistry. In this work, a series of tetraphenylene (TPE)-embedded butterfly bis-crown ether macrocycles (BCE[n], n = 4-7), comprising two crown ether side rings and a TPE core, were synthesized through intramolecular McMurry coupling. Unexpectedly, the presence of flexible oligoethylene chains with varying lengths were found to influence molecular conformation via intramolecular interactions, resulting in the formation of two stabilized conformers with specific semi-rigid symmetric/asymmetric structures (sym-BCE[n] and asym-BCE[n], n = 5, 6). Moreover, it is noteworthy that neither symmetric nor asymmetric conformers are present in the more rigid BCE[4] or the more flexible BCE[7]. Interestingly, these conformers display distinct fluorescence properties and host-guest binding abilities, and only sym-BCE[5] can serve as a host for chiral polymer binding, resulting in the formation of chiral supramolecular assemblies through host-guest interaction induced chirality. Moreover, both circular dichroism (CD) and circularly polarized luminescence (CPL) signals of the obtained assemblies could be switched off by the addition of sodium ion (Na+), suggesting potential applications in the field of dynamic chiral materials.

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Section: Synthesis and Structural Characterizationmentioning

confidence: 93%

Unprecedented TPE-Embedded Butterfly Bis-Crown Ether with Controllable Conformation and Supramolecular Chiroptical Property

Hu,

Tian,

Zuo

et al. 2024

Preprint

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“…35,49 To the best of our knowledge, there are no reports on the application of AIEE-active conjugated polymers for fingermark development. Tetrastyrene (TPE), one of the well-known molecules in the family of AIEgens, is also a highly active chemical reaction intermediate; 51,52 In this study, AIEE-active fluorescent conjugated polymer PTPEPE-IDA was synthesized according to the synthetic route shown in Scheme 1b. Then, PTPEPE-IDA solution was employed as the developing reagent, combining with cotton pad protocol for developing sweat-containing fingermarks on different substrates.…”

Section: Introductionmentioning

confidence: 99%

“…As reported by many studies, introducing AIEgen into the backbone can endow the conjugated polymer with some AIEE property, since the intramolecular motions of AIEgen in the backbone usually is restricted to a certain degree. − These AIEE-active polymers have been widely used in molecular identification, chemical sensing/biosensing, and controlled drug release. ,, In addition, conjugated polymers containing AIE building block in the backbone have also been demonstrated to have good biocompatibility. , To the best of our knowledge, there are no reports on the application of AIEE-active conjugated polymers for fingermark development. Tetrastyrene (TPE), one of the well-known molecules in the family of AIEgens, is also a highly active chemical reaction intermediate; , thus, introducing TPE into the backbone is possible to give AIEE-active conjugated polymer. Therefore, here we are going to synthesize a conjugated polymer (PTPEPE-IDA) containing TPE in the backbone, that is, having poly[ p -(tetraphenylethene)- alt -(phenylene ethylene)] (PTPEPE) as the backbone with two IDA groups and two monocarboxylate groups as the pendant groups in every repeat unit.…”

Section: Introductionmentioning

confidence: 99%

A Universal Developing Strategy for Fingermark Detection and Enhancement Based on Disodium Iminodiacetate-Functionalized Conjugated Polymer

Kong,

Cao,

Zhang

et al. 2024

ACS Appl. Polym. Mater.

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Finding a universal fingermark developing strategy effective for all types of fingermarks may improve the efficiency of forensic investigation. Here, we synthesized a fluorescent conjugated polymer (PTPEPE-IDA) with poly[p-(tetraphenylethene)-alt-(phenylene ethylene)] as the backbone and carrying pendant disodium iminodiacetate and monocarboxylate groups to interact with sweat, which is commonly present in fingermarks. PTPEPE-IDA was dissolved in ethanol to form the developing reagent, which was demonstrated to be effective in visualizing and enhancing sweat-containing sebaceous and blood fingermarks on various substrates with the same developing protocol. With the increase of the sweat content in fingermarks, the fluorescence intensity and clarity of patterns of the developed fingermarks increased. This strategy was effective for sweat-containing fingermarks aged for up to 100 days. The developed fingerprint has high stability, being recognizable after storage for 100 days or immersion in water (or ethanol). Mechanism investigation suggests that PTPEPE-IDA can bind some components in sweat and blood through synergistic effects of multiple interactions, and the aggregation-induced emission enhancement (AIEE) upon sweat was demonstrated by the macroscopic view and emission/absorption spectra, which is beneficial to detect the fingermark quickly and then enhance the legibility of the pattern. This universal strategy is expected to make fingermark development more efficient.

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Molecular Probe for Specific Recognition of TKX‐50: ‘Luminescence‐ON’ Response and its Integration to a Smart Device for Surveillance

Bej,

Dutta,

Pasha

et al. 2024

Small

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In response to the growing concerns about the unauthorized use of advanced secondary explosives such as TKX‐50 against non‐combatant targets, there is an urgent need for effective detection methods or techniques to ensure efficient security screening, homeland security, and public safety. Herein, a new polymeric receptor (IV) derived from functionalized tetraphenylethylene moiety (TPE) and 1,3,5‐tris(4‐aminophenyl)benzene (TAPB) moieties for the efficient detection of TKX‐50 through a ‘switch ON’ luminescence response upon specific binding to the explosive, is reported. The observed ‘luminescence ON’ response is rationalized based on a charge transfer complex formation between TKX‐50 and the polymeric receptor IV (Ka = 1.7 × 104 m−1). This is validated by the steady and excited‐state luminescence studies, along with detailed computational studies. The authors’ presumptions are further validated with adequate control studies using an appropriate monomeric derivative (III) of TPE. Moreover, this ‘luminescence ON’ response can be integrated into a smart and user‐friendly Internet of Things (IoT)‐based prototype device. This device can effectively convert optical responses into digital output to develop an optical device for real‐time detection of TKX‐50 in solution. This lightweight, portable device is ideally suited for remote surveillance and monitoring of TKX‐50; such examples are rare in contemporary literature.

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Tetraphenylethene-based macrocycles with dual-ring topology: synthesis, structures, and applications

Abstract: In the past few decades, macrocycles with different structures and functions have played a crucial role in supramolecular chemistry. Due to its symmetrical structure, simple synthesis process, good stability, and...

Cited by 12 publications

References 83 publications

Unprecedented TPE-Embedded Butterfly Bis-Crown Ether with Controllable Conformation and Supramolecular Chiroptical Property

Unprecedented TPE-Embedded Butterfly Bis-Crown Ether with Controllable Conformation and Supramolecular Chiroptical Property

A Universal Developing Strategy for Fingermark Detection and Enhancement Based on Disodium Iminodiacetate-Functionalized Conjugated Polymer

Molecular Probe for Specific Recognition of TKX‐50: ‘Luminescence‐ON’ Response and its Integration to a Smart Device for Surveillance

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