Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/80494
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dc.contributor.authorLam, TLen_US
dc.contributor.authorTong, KCen_US
dc.contributor.authorYang, Cen_US
dc.contributor.authorKwong, WLen_US
dc.contributor.authorGuan, Xen_US
dc.contributor.authorLi, MDen_US
dc.contributor.authorLo, VKYen_US
dc.contributor.authorChan, SLFen_US
dc.contributor.authorPhillips, DLen_US
dc.contributor.authorLok, CNen_US
dc.contributor.authorChe, CMen_US
dc.date.accessioned2019-03-26T09:17:31Z-
dc.date.available2019-03-26T09:17:31Z-
dc.date.issued2019-
dc.identifier.citationChemical science, 7 Jan. 2019, v. 10, no. 1, p. 293-309en_US
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10397/80494-
dc.description.abstractA panel of iridium(iii) porphyrin complexes containing axial N-heterocyclic carbene (NHC) ligand(s) were synthesized and characterized. X-ray crystal structures of the bis-NHC complexes [Ir-III(ttp)(IMe)(2)](+) (2a), [Ir-III(oep)(BIMe)(2)](+) (2d), [Ir-III(oep)((IPr)-Pr-i)(2)](+) (2e) and [Ir-III(F(20)tpp)(IMe)(2)](+) (2f) display ruffled porphyrin rings with mesocarbon displacements of 0.483-0.594 angstrom and long Ir-C-NHC bonds of 2.100-2.152 angstrom. Variable-temperature H-1 NMR analysis of 2a reveals that the macrocycle porphyrin ring inversion takes place in solution with an activation barrier of 40 +/- 1 kJ mol(-1). The UV-vis absorption spectra of Ir-III(por)-NHC complexes display split Soret bands. TD-DFT calculations and resonance Raman experiments show that the higher-energy Soret band is derived from the (MLCT)-M-1 d(Ir) *(por) transition. The near-infrared phosphorescence of Ir-III(por)-NHC complexes from the porphyrin-based (3)(, *) state features broad emission bands at 701-754 nm with low emission quantum yields and short lifetimes (phi(em) < 0.01; < 4 s). [Ir-III(por)(IMe)(2)](+) complexes (por = ttp and oep) are efficient photosensitizers for O-1(2) generation (phi(so) = 0.64 and 0.88) and are catalytically active in the light-induced aerobic oxidation of secondary amines and arylboronic acid. The bis-NHC complexes exhibit potent dark cytotoxicity towards a panel of cancer cells with IC50 values at submicromolar levels. The cytotoxicity of these complexes could be further enhanced upon light irradiation with IC50 values as low as nanomolar levels in association with the light-induced generation of reactive oxygen species (ROS). Bioimaging of [Ir-III(oep)(IMe)(2)](+) (2c) treated cells indicates that this Ir complex mainly targets the endoplasmic reticulum. [Ir-III(oep)(IMe)(2)](+) catalyzes the photoinduced generation of singlet oxygen and triggers protein oxidation, cell cycle arrest, apoptosis and the inhibition of angiogenesis. It also causes pronounced photoinduced inhibition of tumor growth in a mouse model of human cancer.en_US
dc.description.sponsorshipDepartment of Applied Biology and Chemical Technologyen_US
dc.language.isoenen_US
dc.publisherRoyal Society of Chemistryen_US
dc.relation.ispartofChemical scienceen_US
dc.rightsThis journal is © The Royal Society of Chemistry 2019en_US
dc.rightsThis article is licensed under a Creative Commons Attibution-NonCommercial 3.0 Unported Licence (https://creativecommons.org/licenses/by-nc/3.0/)en_US
dc.rightsThe following publication Lam, T. L., Tong, K. C., Yang, C., Kwong, W. L., Guan, X., Li, M. D., . . . Che, C. M. (2019). Luminescent ruffled iridium(iii) porphyrin complexes containing N-heterocyclic carbene ligands: structures, spectroscopies and potent antitumor activities under dark and light irradiation conditions. Chemical Science, 10(1), 293-309 is available at https://dx.doi.org/10.1039/c8sc02920ben_US
dc.titleLuminescent ruffled iridium(iii) porphyrin complexes containing N-heterocyclic carbene ligands : structures, spectroscopies and potent antitumor activities under dark and light irradiation conditionsen_US
dc.typeJournal/Magazine Articleen_US
dc.identifier.spage293-
dc.identifier.epage309-
dc.identifier.volume10-
dc.identifier.issue1-
dc.identifier.doi10.1039/c8sc02920b-
dc.identifier.isiWOS:000454835000029-
dc.identifier.eissn2041-6539-
dc.description.validate201903 bcrc-
dc.description.oapublished_final-
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