Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 36, Pages 7270-7277Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob00957a
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Funding
- JST-PRESTO [JPMJPR15P5]
- JST-CREST [JPMJCR1902]
- JSPS KAKENHI [21H00158]
- Photo-excitonix Project in Hokkaido University
- Nakajima Foundation
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Ligand release from SiPc dyes can be triggered by X-ray irradiation, and the cleavage of axial ligands occurs through reactions with hydrated electrons generated from water.
Ligand release from silicon phthalocyanine (SiPc) dyes triggered by near-infrared (NIR) light is a key photochemical reaction involving caged compounds based on SiPc. Although NIR light is relatively permeable compared with visible light, this light can be attenuated by tissue absorption and scattering; therefore, using light to induce photochemical reactions deep inside the body is difficult. Herein, because X-rays are highly permeable and can produce radicals through the radiolysis of water, we investigated whether the axial ligands of SiPcs can be cleaved using X-ray irradiation. SiPcs with different axial ligands (alkoxy, siloxy, oxycarbonyl, and phenoxy groups) were irradiated with X-rays under hypoxic conditions. We found that the axial ligands were cleaved via reactions with hydrated electrons (e(aq)(-)), not OH radicals, generated from water in response to X-ray irradiation, and SiPc with alkoxy groups exhibited the highest cleavage efficiency. A quantitative investigation revealed that X-ray-induced axial ligand cleavage proceeds via a radical chain reaction. The reaction is expected to be applicable to the molecular design of X-ray-activatable functional molecules in the future.
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