Metalated Chromene and Chromone Complexes: pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity

Sze Wing Ng; Lai Hon Chung; Chi Fung Yeung; Hoi Shing Lo; Hau Lam Shek; Tian Shu Kang; Chung Hang Leung; Dik Lung Ma; Chun Yuen Wong

doi:10.1002/chem.201705450

Metalated Chromene and Chromone Complexes: pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity

Sze Wing Ng, Lai Hon Chung, Chi Fung Yeung, Hoi Shing Lo, Hau Lam Shek, Tian Shu Kang, Chung Hang Leung, Dik Lung Ma, Chun Yuen Wong^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

23 Citations (Scopus)

Abstract

The two families of Ru^II-chromene and -chromone complexes isolated in this work represent the first examples of metalated chromene and chromone complexes synthesized through transition-metal-mediated cyclization of phenol-tethered ynone. These unprecedented metalated heterocyclic compounds exhibit remarkable features, such as pH-switchable metal–carbon bonding interactions, photo-triggerable release of organic chromone upon visible-light irradiation, and superior antioxidative property to their organic analogue (1,4-benzopyrone). These findings not only offer mechanistic insights into metal-induced activation of functionalized alkynes, but also add a new dimension to rational design of antioxidants and photo-responsive drug delivery systems.

Original language	English
Pages (from-to)	1779-1783
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	8
DOIs	https://doi.org/10.1002/chem.201705450
Publication status	Published - 6 Feb 2018

User-Defined Keywords

alkynes
antioxidants
chromones
photochemistry
ruthenium

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10.1002/chem.201705450

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Ng, S. W., Chung, L. H., Yeung, C. F., Lo, H. S., Shek, H. L., Kang, T. S., Leung, C. H., Ma, D. L., & Wong, C. Y. (2018). Metalated Chromene and Chromone Complexes: pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity. Chemistry - A European Journal, 24(8), 1779-1783. https://doi.org/10.1002/chem.201705450

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title = "Metalated Chromene and Chromone Complexes: pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity",

abstract = "The two families of RuII-chromene and -chromone complexes isolated in this work represent the first examples of metalated chromene and chromone complexes synthesized through transition-metal-mediated cyclization of phenol-tethered ynone. These unprecedented metalated heterocyclic compounds exhibit remarkable features, such as pH-switchable metal–carbon bonding interactions, photo-triggerable release of organic chromone upon visible-light irradiation, and superior antioxidative property to their organic analogue (1,4-benzopyrone). These findings not only offer mechanistic insights into metal-induced activation of functionalized alkynes, but also add a new dimension to rational design of antioxidants and photo-responsive drug delivery systems.",

keywords = "alkynes, antioxidants, chromones, photochemistry, ruthenium",

author = "Ng, {Sze Wing} and Chung, {Lai Hon} and Yeung, {Chi Fung} and Lo, {Hoi Shing} and Shek, {Hau Lam} and Kang, {Tian Shu} and Leung, {Chung Hang} and Ma, {Dik Lung} and Wong, {Chun Yuen}",

note = "Funding Information: The work described in this paper was supported by the Research Grants Council of Hong Kong SAR (CityU 11228316 and T42-103/16-N), the Science Technology and Innovation Committee of Shenzhen Municipality (JCYJ20160229165216275), and by the Shenzhen Research Institute, City University of Hong Kong. We are grateful to Dr. Shek-Man Yiu for X-ray diffraction data collection, and Dr. Man-Kit Tse for NMR data interpretation.",

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day = "6",

doi = "10.1002/chem.201705450",

language = "English",

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pages = "1779--1783",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

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Metalated Chromene and Chromone Complexes: pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity. / Ng, Sze Wing; Chung, Lai Hon; Yeung, Chi Fung et al.
In: Chemistry - A European Journal, Vol. 24, No. 8, 06.02.2018, p. 1779-1783.

Research output: Contribution to journal › Journal article › peer-review

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T1 - Metalated Chromene and Chromone Complexes

T2 - pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity

AU - Ng, Sze Wing

AU - Chung, Lai Hon

AU - Yeung, Chi Fung

AU - Lo, Hoi Shing

AU - Shek, Hau Lam

AU - Kang, Tian Shu

AU - Leung, Chung Hang

AU - Ma, Dik Lung

AU - Wong, Chun Yuen

N1 - Funding Information: The work described in this paper was supported by the Research Grants Council of Hong Kong SAR (CityU 11228316 and T42-103/16-N), the Science Technology and Innovation Committee of Shenzhen Municipality (JCYJ20160229165216275), and by the Shenzhen Research Institute, City University of Hong Kong. We are grateful to Dr. Shek-Man Yiu for X-ray diffraction data collection, and Dr. Man-Kit Tse for NMR data interpretation.

PY - 2018/2/6

Y1 - 2018/2/6

N2 - The two families of RuII-chromene and -chromone complexes isolated in this work represent the first examples of metalated chromene and chromone complexes synthesized through transition-metal-mediated cyclization of phenol-tethered ynone. These unprecedented metalated heterocyclic compounds exhibit remarkable features, such as pH-switchable metal–carbon bonding interactions, photo-triggerable release of organic chromone upon visible-light irradiation, and superior antioxidative property to their organic analogue (1,4-benzopyrone). These findings not only offer mechanistic insights into metal-induced activation of functionalized alkynes, but also add a new dimension to rational design of antioxidants and photo-responsive drug delivery systems.

AB - The two families of RuII-chromene and -chromone complexes isolated in this work represent the first examples of metalated chromene and chromone complexes synthesized through transition-metal-mediated cyclization of phenol-tethered ynone. These unprecedented metalated heterocyclic compounds exhibit remarkable features, such as pH-switchable metal–carbon bonding interactions, photo-triggerable release of organic chromone upon visible-light irradiation, and superior antioxidative property to their organic analogue (1,4-benzopyrone). These findings not only offer mechanistic insights into metal-induced activation of functionalized alkynes, but also add a new dimension to rational design of antioxidants and photo-responsive drug delivery systems.

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KW - antioxidants

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KW - photochemistry

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Metalated Chromene and Chromone Complexes: pH Switchable Metal–Carbon Bonding Interaction, Photo-triggerable Chromone Delivery Application, and Antioxidative Activity

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