Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes

Daniel T. Payne; Whitney A. Webre; Habtom B. Gobeze; Sairaman Seetharaman; Yoshitaka Matsushita; Paul A. Karr; Mandeep K. Chahal; Jan Labuta; Wipakorn Jevasuwan; Naoki Fukata; John S. Fossey; Katsuhiko Ariga; Francis D'Souza; Jonathan P. Hill

doi:10.1039/D0SC00651C

Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes†

Daniel T. Payne,

^a Whitney A. Webre,^b Habtom B. Gobeze,^b Sairaman Seetharaman,^b Yoshitaka Matsushita,

^c Paul A. Karr,^d Mandeep K. Chahal,

^a Jan Labuta,

^a Wipakorn Jevasuwan,^a Naoki Fukata,

^a John S. Fossey,

^e Katsuhiko Ariga,

^af Francis D'Souza

*^b and Jonathan P. Hill

*^a

Author affiliations

* Corresponding authors

^a International Center for Materials Nanoarchitectonics, National Institute for Materials Science, Namiki 1-1, Tsukuba, Ibaraki 305-0044, Japan
E-mail: Jonathan.Hill@nims.go.jp

^b Department of Chemistry, University of North Texas, 1155 Union Circle, 305070 Denton, Texas 76203, USA
E-mail: francis.dsouza@unt.edu

^c Research Network and Facility Services Division, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047, Japan

^d Department of Physical Sciences and Mathematics, Wayne State College, 111 Main Street, Wayne, Nebraska 68787, USA

^e School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, UK

^f Department of Advanced Materials Science, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan

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.

Chemical Science

Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes†

Abstract

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Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes

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