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

Research output: Contribution to journalArticlepeer-review

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

In: Chemical Science, Vol. 11, No. 10, 14.03.2020, p. 2614-2620.

Research output: Contribution to journalArticlepeer-review

Harvard

Payne, DT, Webre, WA, Gobeze, HB, Seetharaman, S, Matsushita, Y, Karr, PA, Chahal, MK, Labuta, J, Jevasuwan, W, Fukata, N, Fossey, JS, Ariga, K, D'Souza, F & Hill, JP 2020, 'Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes', Chemical Science, vol. 11, no. 10, pp. 2614-2620. https://doi.org/10.1039/d0sc00651c

APA

Payne, D. T., Webre, W. A., Gobeze, H. B., Seetharaman, S., Matsushita, Y., Karr, P. A., Chahal, M. K., Labuta, J., Jevasuwan, W., Fukata, N., Fossey, J. S., Ariga, K., D'Souza, F., & Hill, J. P. (2020). Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes. Chemical Science, 11(10), 2614-2620. https://doi.org/10.1039/d0sc00651c

Vancouver

Payne DT, Webre WA, Gobeze HB, Seetharaman S, Matsushita Y, Karr PA et al. Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes. Chemical Science. 2020 Mar 14;11(10):2614-2620. https://doi.org/10.1039/d0sc00651c

Author

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. / Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes. In: Chemical Science. 2020 ; Vol. 11, No. 10. pp. 2614-2620.

Bibtex

@article{981f953a20344f1c8f8d52ec9d56f8cb,
title = "Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes",
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.",
author = "Payne, {Daniel T.} and Webre, {Whitney A.} and Gobeze, {Habtom B.} and Sairaman Seetharaman and Yoshitaka Matsushita and Karr, {Paul A.} and Chahal, {Mandeep K.} and Jan Labuta and Wipakorn Jevasuwan and Naoki Fukata and Fossey, {John S.} and Katsuhiko Ariga and Francis D'Souza and Hill, {Jonathan P.}",
year = "2020",
month = mar,
day = "14",
doi = "10.1039/d0sc00651c",
language = "English",
volume = "11",
pages = "2614--2620",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "10",

}

RIS

TY - JOUR

T1 - Nanomolecular singlet oxygen photosensitizers based on hemiquinonoid-resorcinarenes, the fuchsonarenes

AU - Payne, Daniel T.

AU - Webre, Whitney A.

AU - Gobeze, Habtom B.

AU - Seetharaman, Sairaman

AU - Matsushita, Yoshitaka

AU - Karr, Paul A.

AU - Chahal, Mandeep K.

AU - Labuta, Jan

AU - Jevasuwan, Wipakorn

AU - Fukata, Naoki

AU - Fossey, John S.

AU - Ariga, Katsuhiko

AU - D'Souza, Francis

AU - Hill, Jonathan P.

PY - 2020/3/14

Y1 - 2020/3/14

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85081976299&partnerID=8YFLogxK

U2 - 10.1039/d0sc00651c

DO - 10.1039/d0sc00651c

M3 - Article

C2 - 32206265

AN - SCOPUS:85081976299

VL - 11

SP - 2614

EP - 2620

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 10

ER -