Color-tunable solid-state emissions of Zn(II) and Cd(II) complexes derived from cyano-modified 2-substituted 8-hydroxyquinolines

Huo, Yanping; Pan, Chengqiang; Wang, Songying; Ji, Shaomin; Kong, Tengfei; Gao, Liang; Cai, Ning; Zeng, Huaqiang

doi:10.1016/j.poly.2016.07.028

Cited by 8 publications

(2 citation statements)

References 46 publications

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“…Establishing quinoline derivatives as reliable tectons in supramolecular chemistry is important in this context. However, quinoline is a less explored structural motif in supramolecular chemistry despite its ability to exhibit strong C–H···π and π–π stacking interactions. ,,, The available reports in this direction are mainly on the metal complexes of quinoline derivatives. For example, multinuclear metal complexes, , coordination polymers, , and metal–organic frameworks have been reported using 2S-8HQ derivatives as versatile ligands.…”

Section: Introductionmentioning

confidence: 99%

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

et al. 2022

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Styryl quinolines are biologically active compounds with properties largely depending on the substituents on the styryl and quinoline rings. The supramolecular aspects of this class of compounds are rarely explored. In this study, two new series of styryl quinoline derivatives, bearing −OH and −NO 2 groups at the eighthposition of the quinoline ring and −SCH 3 , −OCH 3 , and −Br groups on the styryl ring, have been developed, and their structural, supramolecular, and cytotoxic properties have been analyzed. Crystallographic analyses revealed the exciting substituent-dependent structural and supramolecular features of these compounds. In general, the 8 −OH substituted derivatives ( SA series) exhibited a non-planar molecular geometry having larger dihedral angles (5.75–59.3°) between the planes of the aromatic rings. At the same time, the 8 −NO 2 substituted derivatives ( SB series) exhibited a more or less planar molecular geometry, as revealed by the smaller dihedral angles (1.32–3.45°) between the aromatic rings. Multiple O–H···O, C–H···O, O–H···N, and π–π stacking interactions among the molecules lead to fascinating supramolecular architectures such as hydrogen-bonded triple helices, zig-zag 1D chains, π–π stacked infinite chains, and so forth in their crystal lattice. Hirshfeld surface analyses confirmed the existence of strong π–π stacking and other weak bonding interactions in these compounds. The preliminary cytotoxic properties of SA and SB series compounds were evaluated against the human cervical cancer cell lines (HeLa cells), which further highlighted the roles of functional substituents on the aromatic rings. The SA series compounds with the −OH substituent on the quinoline ring exhibited better cytotoxicity than the SB series compounds with a −NO 2 substituent. Similarly, the electron-withdrawing group −Br on the styryl ring enhanced the cytotoxicity in both series. The IC 50 values were 2.52–4.69 and 2.897–10.37 μM, respectively, for the SA and SB series compounds. Compound S3A having −OH and −Br groups on the quinoline and styryl ring, respectively, exhibited the best IC 50 value of 2.52 μM among all the compounds tested. These findings confirm the relevance of the hydroxyl group in the eighth position of quinoline. In short, the present study attempts to provide a systematic analysis of the effects of aromatic ring substituents on the structural, supramolecular, and cytotoxic properties of styryl quinolines for the first time.

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Section: Introductionmentioning

confidence: 99%

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

et al. 2022

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“…The crystal structure of L1 derivative with Zn 2+ shows ∼3 Å distance between two Zn 2+ centres, the same is 2.98 Å for L1 with Zn 2+ , as obtained from DFT. On the other hand, for bimetallic Cd 2+ complex, the inter atomic distance is reported as 3.8 Å, 3.55 Å and/or 3.66‐67 Å, [46–48] which is in much higher side than the Zn 2+ congeners. Therefore, it can be presumed that the coordination of Cd 2+ in same fashion may cause a strenuous environment for L1 , which ultimately disfavours the Cd 2+ recognition or sensing in presence of Zn 2+ competitor.…”

Section: Resultsmentioning

confidence: 94%

Zn²⁺ Recognition for Pathogenesis of Pick's Disease via a Luminescent Test Kit

et al. 2021

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The pathogenesis of Pick's disease is feasible by detection of the elevated level of Zn 2 + in the body fluids. This work aims towards developing a suitable chemosensor towards detection of Zn 2 + in human urine specimen and inside eukaryotic cell line. Fluorescence "turn on" in the presence of Zn 2 + makes the chemosensor suitable for its utility in Pick's disease diagnosis. Real urine sample analysis together within cell detection of Zn 2 + was successful which leads towards the design and fabrication of a "ready-to-use" test kit for Zn 2 + recognition from human urine specimen.

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Regular rhombic crystals of Zn(II) complex derived from aromatic nitrile substituted 8-hydroxyquinoline via interface reaction

Kong

Zhang

Cheng

et al. 2022

Journal of Crystal Growth

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Color-tunable solid-state emissions of Zn(II) and Cd(II) complexes derived from cyano-modified 2-substituted 8-hydroxyquinolines

Cited by 8 publications

References 46 publications

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

Zn²⁺ Recognition for Pathogenesis of Pick's Disease via a Luminescent Test Kit

Regular rhombic crystals of Zn(II) complex derived from aromatic nitrile substituted 8-hydroxyquinoline via interface reaction

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Color-tunable solid-state emissions of Zn(II) and Cd(II) complexes derived from cyano-modified 2-substituted 8-hydroxyquinolines

Cited by 8 publications

References 46 publications

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

Substituent-Controlled Structural, Supramolecular, and Cytotoxic Properties of a Series of 2-Styryl-8-nitro and 2-Styryl-8-hydroxy Quinolines

Zn2+ Recognition for Pathogenesis of Pick's Disease via a Luminescent Test Kit

Regular rhombic crystals of Zn(II) complex derived from aromatic nitrile substituted 8-hydroxyquinoline via interface reaction

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Product

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Zn²⁺ Recognition for Pathogenesis of Pick's Disease via a Luminescent Test Kit