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Slanina T, Shrestha P, Palao E, et al. In Search of the Perfect Photocage: Structure-Reactivity Relationships in meso-Methyl BODIPY Photoremovable Protecting Groups. J Am Chem Soc. 2017;139(42):15168-15175doi: 10.1021/jacs.7b08532.
Slanina, T., Shrestha, P., Palao, E., Kand, D., Peterson, J. A., Dutton, A. S., Rubinstein, N., Weinstain, R., Winter, A. H., & Klán, P. (2017). In Search of the Perfect Photocage: Structure-Reactivity Relationships in meso-Methyl BODIPY Photoremovable Protecting Groups. Journal of the American Chemical Society, 139(42), 15168-15175. https://doi.org/10.1021/jacs.7b08532
Slanina, Tomáš, et al. "In Search of the Perfect Photocage: Structure-Reactivity Relationships in meso-Methyl BODIPY Photoremovable Protecting Groups." Journal of the American Chemical Society vol. 139,42 (2017): 15168-15175. doi: https://doi.org/10.1021/jacs.7b08532
Slanina T, Shrestha P, Palao E, Kand D, Peterson JA, Dutton AS, Rubinstein N, Weinstain R, Winter AH, Klán P. In Search of the Perfect Photocage: Structure-Reactivity Relationships in meso-Methyl BODIPY Photoremovable Protecting Groups. J Am Chem Soc. 2017 Oct 25;139(42):15168-15175. doi: 10.1021/jacs.7b08532. Epub 2017 Oct 17. PMID: 29039200.
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J Am Chem Soc. 2017 Oct 25;139(42):15168-15175. doi: 10.1021/jacs.7b08532. Epub 2017 Oct 17.

In Search of the Perfect Photocage: Structure-Reactivity Relationships in meso-Methyl BODIPY Photoremovable Protecting Groups.

Journal of the American Chemical Society

Tomáš Slanina, Pradeep Shrestha, Eduardo Palao, Dnyaneshwar Kand, Julie A Peterson, Andrew S Dutton, Naama Rubinstein, Roy Weinstain, Arthur H Winter, Petr Klán

Affiliations

  1. Department of Chemistry and RECETOX, Faculty of Science, Masaryk University , Kamenice 5, 625 00, Brno, Czech Republic.
  2. Institute of Organic Chemistry and Chemical Biology, Goethe University Frankfurt , 60323 Frankfurt am Main, Germany.
  3. Department of Chemistry, Iowa State University , 1608 Gilman Hall, Ames, Iowa 50010, United States.
  4. School of Plant Sciences and Food Security, Faculty of Life Sciences, Tel-Aviv University , Tel-Aviv 6997801, Israel.

PMID: 29039200 DOI: 10.1021/jacs.7b08532

Abstract

A detailed investigation of the photophysical parameters and photochemical reactivity of meso-methyl BODIPY photoremovable protecting groups was accomplished through systematic variation of the leaving group (LG) and core substituents as well as substitutions at boron. Efficiencies of the LG release were evaluated using both steady-state and transient absorption spectroscopies as well as computational analyses to identify the optimal structural features. We find that the quantum yields for photorelease with this photocage are highly sensitive to substituent effects. In particular, we find that the quantum yields of photorelease are improved with derivatives with higher intersystem crossing quantum yields, which can be promoted by core heavy atoms. Moreover, release quantum yields are dramatically improved by boron alkylation, whereas alkylation in the meso-methyl position has no effect. Better LGs are released considerably more efficiently than poorer LGs. We find that these substituent effects are additive, for example, a 2,6-diiodo-B-dimethyl BODIPY photocage features quantum yields of 28% for the mediocre LG acetate and a 95% quantum yield of release for chloride. The high chemical and quantum yields combined with the outstanding absorption properties of BODIPY dyes lead to photocages with uncaging cross sections over 10 000 M

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