Details

Autor(en) / Beteiligte

• 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.

Titel

Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes† †Electronic supplementary information (ESI) available. CCDC 1934744–1934750. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d0sc00651c

Ist Teil von

• Chemical science (Cambridge), 2020-02, Vol.11 (10), p.2614-2620

Ort / Verlag

Royal Society of Chemistry

Erscheinungsjahr

2020

Quelle

EZB Free E-Journals

Beschreibungen/Notizen

• 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. 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.