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Issue 1, 2017
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(E)-4-Methyl-N-((quinolin-2-yl)ethylidene)aniline as ligand for IIB supramolecular complexes: synthesis, structure, aggregation-induced emission enhancement and application in PMMA-doped hybrid material

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Abstract

Judicious structural design employing 2-quinolinecarboxaldehyde and 4-methylaniline was used to generate the Schiff base ligand (E)-4-methyl-N-((quinolin-2-yl)ethylidene)aniline (L). Five IIB complexes, namely, [ZnLCl2] (1), [ZnL(NO3)2] (2), [ZnL(OAc)2]3 (3), [CdL(OAc)2]3 (4), and [HgLCl2] (5) have been synthesized based on L. Single-crystal X-ray diffraction analysis indicates that complexes 1, 3 and 4 exhibit 3D networks, whereas 2 and 5 form 2D layers and 1D chains, respectively. TD-DFT calculations show a good correlation with the UV-vis absorption assigned to π → π* intraligand transitions. Furthermore, complexes 1–5 displayed strong greenish luminescent emissions (518–524 nm) in the aggregate state but weak emissions in solution (aggregation-induced emission enhancement), which may be due to the existence of C–H⋯Cl/O hydrogen bonding and π⋯π stacking interactions, resulting in restriction of intramolecular rotation (RIR). Variable-concentration 1H NMR studies suggested that the aggregates undergo intramolecular changes in conformation due to intermolecular interactions. Moreover, the emission intensity and lifetime exhibited obvious increases induced by mechanical grinding and temperature reduction, which were also attributed to AIEE properties. Subsequently, complex 1 was incorporated into poly(methyl methacrylate) (PMMA), whereby 1-PMMA exhibited enhanced emission intensity (20-fold increase in comparison with that of 1), which offers opportunities for use in plastic greenhouses to increase leaf photosynthesis.

Graphical abstract: (E)-4-Methyl-N-((quinolin-2-yl)ethylidene)aniline as ligand for IIB supramolecular complexes: synthesis, structure, aggregation-induced emission enhancement and application in PMMA-doped hybrid material

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Publication details

The article was received on 05 Oct 2016, accepted on 15 Nov 2016 and first published on 16 Nov 2016


Article type: Paper
DOI: 10.1039/C6DT03853K
Dalton Trans., 2017,46, 71-85

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    (E)-4-Methyl-N-((quinolin-2-yl)ethylidene)aniline as ligand for IIB supramolecular complexes: synthesis, structure, aggregation-induced emission enhancement and application in PMMA-doped hybrid material

    A. Wang, R. Fan, Y. Dong, W. Chen, Y. Song, P. Wang, S. Hao, Z. Liu and Y. Yang, Dalton Trans., 2017, 46, 71
    DOI: 10.1039/C6DT03853K

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