{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Iida N"],"funding":["Japan Society for the Promotion of Science (JSPS) Grants-in-Aid of Scientific Research (B) Program","Advanced Catalytic Transformation (ACT-C) Fund from the Japan Science and Technology (JST) Agency","MEXT: Ministry of Education, Culture, Sports, Science & Technology (Japan) Platform for Drug Discovery, Informatics, and Structural Life Science","Daiko Foundation"],"pagination":["698-702"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4906510"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["4(6)"],"pubmed_abstract":["The pentafluorosulfanyl (SF5) group is more electronegative, lipophilic and sterically bulky relative to the well-explored trifluoromethyl (CF3) group. As such, the SF5 group could offer access to pharmaceuticals, agrochemicals and optoelectronic materials with novel properties. Here, the first synthesis of phthalocyanines (Pcs), a class of compounds used as dyes and with potential as photodynamic therapeutics, with a SF5 group directly attached on their peripheral positions is disclosed. The key for this work is the preparation of a series of SF5-containing phthalonitriles, which was beautifully regio-controlled by a stepwise cyanation via ortho-lithiation/iodination from commercially available pentafluorosulfanyl arenes. The macrocyclization of the SF5-containing phthalonitriles to SF5-substituted Pcs required harsh conditions with the exception of the synthesis of β-SF5-substituted Pc. The regiospecificity of the newly developed SF5-substituted Pcs observed by UV/Vis spectra and fluorescence quantum yields depend on the peripheral positon of the SF5 group."],"journal":["ChemistryOpen"],"pubmed_title":["Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions."],"pmcid":["PMC4906510"],"funding_grant_id":["25288045"],"pubmed_authors":["Iida N","Mori S","Tanaka K","Saito N","Shibata N","Tokunaga E"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions.","description":"The pentafluorosulfanyl (SF5) group is more electronegative, lipophilic and sterically bulky relative to the well-explored trifluoromethyl (CF3) group. As such, the SF5 group could offer access to pharmaceuticals, agrochemicals and optoelectronic materials with novel properties. Here, the first synthesis of phthalocyanines (Pcs), a class of compounds used as dyes and with potential as photodynamic therapeutics, with a SF5 group directly attached on their peripheral positions is disclosed. The key for this work is the preparation of a series of SF5-containing phthalonitriles, which was beautifully regio-controlled by a stepwise cyanation via ortho-lithiation/iodination from commercially available pentafluorosulfanyl arenes. The macrocyclization of the SF5-containing phthalonitriles to SF5-substituted Pcs required harsh conditions with the exception of the synthesis of β-SF5-substituted Pc. The regiospecificity of the newly developed SF5-substituted Pcs observed by UV/Vis spectra and fluorescence quantum yields depend on the peripheral positon of the SF5 group.","dates":{"release":"2015-01-01T00:00:00Z","publication":"2015 Dec","modification":"2024-10-18T23:55:39.169Z","creation":"2019-03-27T02:15:59Z"},"accession":"S-EPMC4906510","cross_references":{"pubmed":["27308194"],"doi":["10.1002/open.201500165"]}}