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Restriction of Conformation Transformation in Excited State: An Aggregation-Induced Emission Building Block Based on Stable Exocyclic C=N Group.

ABSTRACT: The development of aggregation-induced emission (AIE) building block and deciphering its luminescence mechanism are of great significance. Here a feasible strategy for the construction of AIE unit based on E-Z isomerization (EZI) of exocyclic C=N double bond is proposed. Taking [1,2,4]thiadiazole[4,3-a]pyridine (TZP) derivative as an example, its aryl-substituted derivative (TZPP) shows obvious AIE character. The analysis of spectral data and theoretical calculations indicates that fast structural relaxation of TZPP in the emissive state plays a key role in a low fluorescence quantum yield in dilute solution, which should be caused by the small energy gap between locally excited (LE) state and twisted intramolecular charge transfer state. When in solid state, the bright emission with LE state characteristic reappears due to the large shift barrier of geometry transformation. As a potential building block for AIEgens with special heterocyclic structure, these findings would open up opportunities for developing various functional materials.

SUBMITTER: Yu W

PROVIDER: S-EPMC7566090 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Restriction of Conformation Transformation in Excited State: An Aggregation-Induced Emission Building Block Based on Stable Exocyclic C=N Group.

Yu Wentao W Zhang Han H Yin Ping-An PA Zhou Fan F Wang Zhiming Z Wu Wanqing W Peng Qian Q Jiang Huanfeng H Tang Ben Zhong BZ

iScience 20200919 10

The development of aggregation-induced emission (AIE) building block and deciphering its luminescence mechanism are of great significance. Here a feasible strategy for the construction of AIE unit based on E-Z isomerization (EZI) of exocyclic C=N double bond is proposed. Taking [1,2,4]thiadiazole[4,3-a]pyridine (TZP) derivative as an example, its aryl-substituted derivative (TZPP) shows obvious AIE character. The analysis of spectral data and theoretical calculations indicat ...[more]

PMID: 33089098

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Project description:Polycyclic aromatic hydrocarbons (PAHs) with boron-nitrogen (BN) moieties have attracted tremendous interest due to their intriguing electronic and optoelectronic properties. However, most of the BN-fused π-systems reported to date are difficult to modify and exhibit traditional aggregation-caused quenching (ACQ) characteristics. This phenomenon greatly limits their scope of application. Thus, continuing efforts to seek novel, structurally distinct and functionally diverse structures are highly desirable. Herein, we proposed a one-stone-two-birds strategy including simultaneous exploration of reactivity and tuning of the optical and electronic properties for BN-containing π-skeletons through flexible regioselective functionalization engineering. In this way, three novel functionalized BN luminogens (DPA-BN-BFT, MeO-DPA-BN-BFT and DMA-DPA-BN-BFT) with similar structures were obtained. Intriguingly, DPA-BN-BFT, MeO-DPA-BN-BFT and DMA-DPA-BN-BFT exhibit completely different emission behaviors. Fluorogens DPA-BN-BFT and MeO-DPA-BN-BFT exhibit a typical ACQ effect; in sharp contrast, DMA-DPA-BN-BFT possesses a prominent aggregation induced emission (AIE) effect. To the best of our knowledge, this is the first report to integrate ACQ and AIE properties into one BN aromatic backbone with subtle modified structures. Comprehensive analysis of the crystal structure and theoretical calculations reveal that relatively large twisting angles, multiple intermolecular interactions and tight crystal packing modes endow DMA-DPA-BN-BFT with strong AIE behavior. More importantly, cell imaging demonstrated that luminescent materials DPA-BN-BFT and DMA-DPA-BN-BFT can highly selectively and sensitively detect lipid droplets (LDs) in living MCF-7 cells. Overall, this work provides a new viewpoint of the rational design and synthesis of advanced BN-polycyclic aromatics with AIE features and triggers the discovery of new functions and properties of azaborine chemistry.

Dataset Information

Restriction of Conformation Transformation in Excited State: An Aggregation-Induced Emission Building Block Based on Stable Exocyclic C=N Group.

Publications

Restriction of Conformation Transformation in Excited State: An Aggregation-Induced Emission Building Block Based on Stable Exocyclic C=N Group.

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