Highly photostable silicon(IV) phthalocyanines containing adamantane moieties: synthesis, structure, and properties

• Published in: Tetrahedron Vol. 66; no. 46; pp. 9041 - 9048
• Main Authors: Shen, Xiao-Min, Jiang, Xiong-Jie, Huang, Chang-Chang, Zhang, Han-Hui, Huang, Jian-Dong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 13.11.2010; Elsevier
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Exact sciences and technology; Organic chemistry; Photosensitizer; Photostability; Phthalocyanine; Physical Sciences; Preparations and properties; Science & Technology; Synthesis; Phthalocyanine; ORUZAKITZPLOLW-CYHMSPKMSA-N; Synthesis; Photosensitizer; CPBKQDFXKFYXLE-KGTMRQIWSA-N; Photostability; DENDRITIC PHTHALOCYANINES; SPECTROSCOPIC PROPERTIES; PHOTOBIOLOGICAL PROPERTIES; PHOTOPHYSICAL PROPERTIES; IN-VITRO; THERAPY; OXYGEN QUANTUM YIELDS; VITRO PHOTODYNAMIC ACTIVITIES; BOVINE SERUM-ALBUMIN; AGGREGATION BEHAVIOR; Molecular structure; Molecular interaction; Non metal Complexes; Characterization; Biocompatibility; Silicon; Chemical synthesis; Zinc Complexes; Solvent; Non metal phthalocyanine; Ungulata; Molecular rigidity; Bovine; Steric hindrance; Singlet state; Silicon Complexes; Serum albumin; Transition metal Complexes; Quantum yield; X ray diffraction; Vertebrata; Mammalia; Metallophthalocyanine; Irradiation; Photochemical stability; Artiodactyla; Conjugated compound; Crystalline structure
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.09.007

Two new axially disubstituted silicon(IV) phthalocyanines 1 and 2 have been synthesized by treating silicon phthalocyanine dichloride with 1-adamantanemethanol or 1-adamamtaneethanol, respectively. The crystal structure of compound 2 has been characterized by X-ray diffraction analysis. Both compounds are efficient singlet-oxygen generator with a quantum yield of 0.40–0.43. With two rigid bulky adamantane moieties at the axial positions, these phthalocyanines not only are essentially non-aggregated in common solvents, but also exhibit a high photostability. They are about 100 times more stable than zinc phthalocyanine under the same irradiation conditions. With the goal of enhancing the biocompatibilities, interactions and conjugations of these two compounds with bovine serum albumin have also been investigated. [Display omitted]