A new V-shaped 2H-imidazole-based spirocyclic fluorophore: Aggregation-induced emission, twisted intramolecular charge transfer, and high responsiveness to trace water and acid

Du, Feiyue; Li, Dongqin; Ge, Sheng; Xie, Shumei; Xu, Ziqiang; Wang, Erjing; Wang, Shimin; Tang, Ben Zhong

doi:10.1016/j.dyepig.2021.109640

Cited by 12 publications

(4 citation statements)

References 47 publications

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“…In the AIE toolbox, there is another kind of AIEgens featured a D-𝜋-A structure, whose emission behaviors are heavily dependent on the surrounding polarities. [97][98] Generally, the emission of a D-𝜋-A AIEgen is from a locally excited state (LE) in a nonpolar environment, and the emission would be redshifted from a twisted intramolecular charge transfer state (TICT) in a more polar environment. Therefore, TICT AIEgens are supposed to be able to discern the polymers in a blend based on emission color difference.…”

Section: Microphase Separation In Polymer Blendmentioning

confidence: 99%

Aggregation‐Induced Emission Boosting the Study of Polymer Science

Wang

et al. 2022

Macromol. Rapid Commun.

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Dedicated to Professor Daoben Zhu on the occasion of his 80th birthday The past one hundred years have witnessed the great development of polymer science. The advancement of polymer science is closely related with the development of characterization techniques and methods, from viscometry in molecular weight determination to advanced techniques including differential scanning calorimetry, nuclear magnetic resonance, and scanning electron microscopy. However, these techniques are normally constrained to tedious sample preparation, high costs, harsh experimental conditions, or ex situ characterization. Fluorescence technology has the merits of high sensitivity and direct visualization. Contrary to conventional aggregation-causing quenching fluorophores, those dyes with aggregation-induced emission (AIE) characteristics show high emission efficiency in aggregate states. Based on the restriction of intramolecular motions for AIE properties, the AIE materials are very sensitive to the surrounding microenvironments owing to the twisted propeller-like structures and therefore offer great potential in the study of polymers. The AIE concept has been successfully used in polymer science and provides a deeper understanding on polymer structure and properties. In this review, the applications of AIEgens in polymer science for visualizing polymerization, glass transition, dissolution, crystallization, gelation, self-assembly, phase separation, cracking, and self-healing are exemplified and summarized. Lastly, the challenges and perspectives in the study of polymer science using AIEgens are addressed.

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Section: Microphase Separation In Polymer Blendmentioning

confidence: 99%

Aggregation‐Induced Emission Boosting the Study of Polymer Science

Wang

et al. 2022

Macromol. Rapid Commun.

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“…[22][23][24][25] Some Janus luminogens and V-and dragonfly-shaped AIEgens have been investigated. [26][27][28][29] However, the twisted architecture often blue-shifts the absorption and emission maxima. Therefore, it remains challenging to develop NIR fluorophores with maximum absorption/emission at longer wavelengths with high fluorescence quantum yields (QYs).…”

Section: Design Synthesis and Solvatochromic Behaviormentioning

confidence: 99%

A novel windmill-shaped AIE-active pyrrolopyrrole cyanine: design, synthesis and efficient hydrazine detection

et al. 2022

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“…20,21 Therefore, taking advantage of the compensation effect of AIE, the integration of AIE and TICT features in a single molecule is supposed to enhance the emission of TICT materials while preserving their TICT nature. Until now, several low-mass luminogens with TICT−AIE features have been developed, such as 4,4′-(spiro[fluorene-9,2′-imidazole]-4′,5′-diyl)bis(N,N-diphenylaniline) (DPS-DPA), 22 3,6-divinylaryl-substituted carbazole (C12P), 23 TPP-TPA, 24 and BODIPY derivatives. 15 As an indispensable branch of AIE luminogens, non-conventional AIE polymers devoid of remarkable conjugates play critical roles due to their excellent biocompatibility, water solubility, and simple processes.…”

Section: Introductionmentioning

confidence: 99%

“…Until now, several low-mass luminogens with TICT–AIE features have been developed, such as 4,4′-(spiro[fluorene-9,2′-imidazole]-4′,5′-diyl)bis( N , N -diphenylaniline) (DPS-DPA), 3,6-divinylaryl-substituted carbazole (C12P), TPP-TPA, and BODIPY derivatives . As an indispensable branch of AIE luminogens, non-conventional AIE polymers devoid of remarkable conjugates play critical roles due to their excellent biocompatibility, water solubility, and simple processes. − Among various non-conventional AIE polymers, the hyperbranched polysiloxane (HBPSi) is a class of newly emerging silicon hetero-atomic AIE luminophores, which contain a Si–O–C chain segment as the backbone. , The flexible Si–O–C chains and abundant silicon atoms with empty 3d orbitals endow HBPSi with excellent luminescent properties, which can be finely tuned by altering interspace configurations. , However, non-conventional AIE polymers with TICT features have been seldom studied, and the silicon-bridged non-conventional TICT-AIE polymer remains a puzzle.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Emission of a Nonconventional Aggregation-Induced Emission Polymer via Silicon-Bridged Twisted Intramolecular Charge Transfer for Targeted Delivery and Visualized Drug Release

Zhao

et al. 2023

Biomacromolecules

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The design of tunable luminescent biomaterials with large Stokes shifts is usually pursued by a twisted intramolecular charge transfer (TICT) effect with switchable emission colors in response to various external stimuli. However, such a strategy is usually realized in conjugated molecules containing benzene or its derivatives and consequently suffers from poor biocompatibility. In this work, a hyperbranched polysiloxane (HBPSi)-based nonconjugated fluorescent polymer with TICT and aggregationinduced emission (AIE) features is developed, and its luminescent properties, fluorescence mechanism, and potential applications are investigated. Initially, the non-conjugated HBPSi exhibits remarkable AIE characteristics due to the formation of through-space conjugation. With the introduction of the sulfur atom, a non-conjugated D−A type AIE material, HBPSi-Cys, that exhibits a dualstate emission with a large Stokes shift of 213 nm, is obtained. The correlation of the lower-energy emission band with solvent polarity suggests the existence of the TICT state. TICT and AIE characteristics direct different properties of HBPSi-Cys, with TICT regulating solvatochromic emission wavelengths and AIE manipulating the emission intensity with a compensation effect. Density functional theory calculations reveal that the non-conjugated D−A structure in HBPSi-Cys was formed across the silicon bridge, with auxochromic sulfhydryl groups and adjacent amide groups as acceptor units and amine and hydroxyl groups as donor units. Additionally, the AIE-active HBPSi could be utilized as a fluorescent probe for the analysis of metal ions. After grafting the AS1411 aptamer to HBPSi-Cys as the recognition motif, HBPSi-Apt possesses excellent targeted bioimaging, drug loading, pH/GSH dualresponsive drug release, and visualized drug delivery performance. This work provides a new way to design functional AIE polymers with tunable optical properties, and the synthesized HBPSi-Cys shows great potential as a smart fluorescent biomaterial.

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A new V-shaped 2H-imidazole-based spirocyclic fluorophore: Aggregation-induced emission, twisted intramolecular charge transfer, and high responsiveness to trace water and acid

Cited by 12 publications

References 47 publications

Aggregation‐Induced Emission Boosting the Study of Polymer Science

Aggregation‐Induced Emission Boosting the Study of Polymer Science

A novel windmill-shaped AIE-active pyrrolopyrrole cyanine: design, synthesis and efficient hydrazine detection

Tuning the Emission of a Nonconventional Aggregation-Induced Emission Polymer via Silicon-Bridged Twisted Intramolecular Charge Transfer for Targeted Delivery and Visualized Drug Release

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