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Substituent Effect on AIE mechanism of two coumarin derivatives: uncommon TICT fluorescence in aggregation state

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Abstract

Two coumarin derivatives, 7-diethylamino-3-(4-nitrophenyl)coumarin (DNC) and 7-hydroxy-3-(4-nitrophenyl)coumarin (HNC), were synthesized via Knoevenagel condensation of salicylaldehyde derivatives with 4-nitrophenylacetonitrile and then cyclization reaction. Both of them were characterized by single-crystal X-ray diffraction. The molecules of DNC are stacked via π-π interaction, while the hydrogen bond interactions instead of π-π interaction were observed in the crystal packing of HNC. Both of DNC and HNC showed solvatochromic properties and aggregation-induced emission (AIE) activities, but the AIE characteristics of them were entirely different. HNC exhibited an AIE phenomenon as the result of the restriction of twisted intramolecular charge transfer (TICT), while DNC emitted peculiar dual fluorescence which was assigned to the emission based on the inhibition of TICT state formation and the emission from the TICT state respectively.

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Availability of data and material/Data availability

The crystallographic information files that have been deposited in the Cambridge Crystallographic Data Centre (CCDC 2,130,543 for DNC and 2,130,544 for HNC) which are freely available for all. The link for CCDC: https://www.ccdc.cam.ac.uk/.

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Funding

This work is financially supported by the National Natural Science Foundation of China (22061016) and Program for Innovative Research Team in University (IRT-16R19).

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Authors and Affiliations

  1. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry & Chemical Engineering, Hainan normal University, 571158, Haikou, China

    Qiao Li, Yang Zhao, Zhigang Niu & Enju Wang

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  1. Qiao Li
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  2. Yang Zhao
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  3. Zhigang Niu
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  4. Enju Wang
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Contributions

EW contributed to the study conception and design, and was the major contributor in writing the manuscript. The synthesis, spectrum test, data analysis and so on were performed by QL with the assistance of YZ. The X-ray diffraction data collection and structure determination was performed by ZN.

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Correspondence to Enju Wang.

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Li, Q., Zhao, Y., Niu, Z. et al. Substituent Effect on AIE mechanism of two coumarin derivatives: uncommon TICT fluorescence in aggregation state. J Fluoresc 32, 1443–1448 (2022). https://doi.org/10.1007/s10895-022-02933-2

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  • DOI: https://doi.org/10.1007/s10895-022-02933-2

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