Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes. Issue 10 (18th February 2020)

• Record Type: Journal Article
• Authors: Payne, Daniel T.; Webre, Whitney A.; Gobeze, Habtom B.; Seetharaman, Sairaman; Matsushita, Yoshitaka; Karr, Paul A.; Chahal, Mandeep K.; Labuta, Jan; Jevasuwan, Wipakorn; Fukata, Naoki; Fossey, John S.; Ariga, Katsuhiko; D'Souza, Francis; Hill, Jonathan P.
• Is Part Of: Chemical science. Volume 11:Issue 10(2020)
• Page Start: 2614
• Page End: 2620
• Publication Date: 2020-02-18
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc00651c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Singlet oxygen sensitization involving a class of hemiquinonoid-substituted resorcinarenes prepared from the corresponding 3, 5-di- t -butyl-4-hydroxyphenyl-substituted resorcinarenes is reported. Abstract : Singlet oxygen sensitization involving a class of hemiquinonoid-substituted resorcinarenes prepared from the corresponding 3, 5-di- t -butyl-4-hydroxyphenyl-substituted resorcinarenes is reported. Based on variation in the molecular structures, quantum yields comparable with that of the well-known photosensitizing compound meso -tetraphenylporphyrin were obtained for the octabenzyloxy-substituted double hemiquinonoid resorcinarene reported herein. The following classes of compounds were studied: benzyloxy-substituted resorcinarenes, acetyloxy-substituted resorcinarenes and acetyloxy-substituted pyrogallarenes. Single crystal X-ray crystallographic analyses revealed structural variations in the compounds with conformation ( i.e., rctt, rccc, rcct) having some influence on the identity of hemiquinonoid product available. Multiplicity of hemiquinonoid group affects singlet oxygen quantum yield with those doubly substituted being more active than those containing a single hemiquinone. Compounds reported here lacking hemiquinonoid groups are inactive as photosensitizers. The term 'fuchsonarene' (fuchson + arene of resorcinarene) is proposed for use to classify the compounds.