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

24 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.",

year = "2018",

month = feb,

day = "6",

doi = "10.1002/chem.201705450",

language = "English",

volume = "24",

pages = "1779--1783",

journal = "Chemistry - A European Journal",

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publisher = "John Wiley \& Sons Ltd",

number = "8",

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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

TY - JOUR

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.

KW - alkynes

KW - antioxidants

KW - chromones

KW - photochemistry

KW - ruthenium

UR - https://www.scopus.com/pages/publications/85041587808

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DO - 10.1002/chem.201705450

M3 - Journal article

C2 - 29160601

AN - SCOPUS:85041587808

SN - 0947-6539

VL - 24

SP - 1779

EP - 1783

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 8

ER -

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

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