PDF herunterladen
Synlett 2022; 33(03): 247-258
DOI: 10.1055/s-0041-1737792
new tools

Tuning the Electrochemical and Photophysical Properties of Osmium-Based Photoredox Catalysts

Samantha L. Goldschmid
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
,
Eva Bednářová‡
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
,
Logan R. Beck‡
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
,
Katherine Xie
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
,
Nicholas E. S. Tay
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
,
Benjamin D. Ravetz
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
,
Jun Li
b   Chemical Process Development, Bristol Myers Squibb, New Brunswick, New Jersey 08903, USA
,
Candice L. Joe
b   Chemical Process Development, Bristol Myers Squibb, New Brunswick, New Jersey 08903, USA
,
Tomislav Rovis  ∗
a   Department of Chemistry, Columbia University, New York, New York 10027, USA
› InstitutsangabenE.B. acknowledges the Experientia Foundation for a postdoctoral fellowship. We are grateful to Bristol-Myers Squibb for support.
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

The use of low-energy deep-red (DR) and near-infrared (NIR) light to excite chromophores enables catalysis to ensue across barriers such as materials and tissues. Herein, we report the detailed photophysical characterization of a library of OsII polypyridyl photosensitizers that absorb low-energy light. By tuning ligand scaffold and electron density, we access a range of synthetically useful excited state energies and redox potentials.

1 Introduction

1.1 Scope

1.2 Measuring Ground-State Redox Potentials

1.3 Measuring Photophysical Properties

1.4 Synthesis of Osmium Complexes

2 Properties of Osmium Complexes

2.1 Redox Potentials of Os(L)2-Type Complexes

2.2 Redox Potentials of Os(L)3-Type Complexes

2.3 UV/Vis Absorption and Emission Spectroscopy

3 Conclusions

Key words

photoredox catalysis - near-infrared - ligand design

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737792.
  • Supporting Information


Publikationsverlauf

Eingereicht: 16. November 2021

Angenommen nach Revision: 29. Dezember 2021

Artikel online veröffentlicht:
14. Januar 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

  • 1 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
    CrossrefPubMed
  • 2 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
    CrossrefPubMed
  • 3 Ravetz BD, Pun AB, Churchill EM, Congreve DN, Rovis T, Campos LM. Nature 2019; 565: 343
    CrossrefPubMed
  • 4 Ravetz BD, Tay NE. S, Joe CL, Sezen-Edmonds M, Schmidt MA, Tan Y, Janey JM, Eastgate MD, Rovis T. ACS Cent. Sci. 2020; 6: 2053
    CrossrefPubMed
  • 5 Mei L, Veleta JM, Gianetti TL. J. Am. Chem. Soc. 2020; 142: 12056
    CrossrefPubMed
  • 6 Demadis KD, Dattelbaum DM, Kober EM, Concepcion JJ, Paul JJ, Meyer TJ, White PS. Inorg. Chim. Acta 2007; 360: 1143
    Crossref
  • 7 Stull SM, Mei L, Gianetti TL. Synlett 2021; in press; DOI: 10.1055/a-1665-9220
  • 8 Wang C, Zhang H, Zhang T, Zou X, Wang H, Rosenberger JE, Vannam R, Trout WS, Grimm JB, Lavis LD, Thorpe C, Jia X, Li Z, Fox JM. J. Am. Chem. Soc. 2021; 143: 10793
    CrossrefPubMed
  • 9 Fajardo JJr, Barth AT, Morales M, Takase MK, Winkler JR, Gray HB. J. Am. Chem. Soc. 2021; 143: 19389
    CrossrefPubMed
  • 10 Lechner VM, Nappi M, Deneny PJ, Folliet S, Chu JC. K, Gaunt MJ. Chem. Rev. 2021; in press; DOI DOI: 10.1021/acs.chemrev.1c00357.
    CrossrefPubMed
  • 11 Thompson DW, Ito A, Meyer T. J. Pure Appl. Chem. 2013; 85: 1257
    Crossref
  • 12 van der Westhuizen D, Conradie J, von Eschwege KG. Electroanalysis 2020; 32: 2838
    Crossref
  • 13 Liu A, Anzai J, Wang J. Bioelectrochemistry 2005; 67: 1
    CrossrefPubMed
  • 14 Liu Y, De Nicola A, Reiff O, Ziessel R, Schanze KS. J. Phys. Chem. A 2003; 107: 3476
    Crossref
  • 15 Bard AJ, Faulkner LR. Electrochemical Methods: Fundamentals and Applications, 2nd ed. Harris D, Swain E. John Wiley & Sons; New York: 2004
    Google Scholar
  • 16 Gritzner G, Kuta J. Pure Appl. Chem. 1984; 56: 461
    Crossref
  • 17 Elgrishi N, Rountree KJ, McCarthy BD, Rountree ES, Eisenhart TT, Dempsey JL. J. Chem. Educ. 2017; 95: 197
    CrossrefPubMed
  • 18 Jones WE, Fox MA. J. Phys. Chem. 1994; 98: 5095
    Crossref
  • 19 Oda N, Tsuji K, Ichimura A. Anal. Sci. 2001; 17: 375
    CrossrefPubMed
  • 20 Riis-Johannessen T, Dupont N, Canard G, Bernardinelli G, Hauser A, Piguet C. Dalton Trans. 2008; 3661
    CrossrefPubMed
  • 21 Johnson SR, Westmoreland TD, Caspar JV, Barqawi KR, Meyer T. J. Inorg. Chem. 1988; 27: 3195
    Crossref
  • 22 Xu W, Peng B, Chen J, Liang M, Cai F. J. Phys. Chem. C 2008; 112: 874
    Crossref
  • 23 Till NA, Tian L, Dong Z, Scholes GD, MacMillan DW. C. J. Am. Chem. Soc. 2020; 142: 15830
    CrossrefPubMed
  • 24 Kandoth N, Hernández JP, Palomares E, Lloret-Fillol J. Sustainable Energy Fuels 2021; 5: 638
    Crossref
  • 25 Ondongo OS, Endicott JF. Inorg. Chem. 2009; 48: 2818
    CrossrefPubMed
  • 26 Shao JY, Zhong YW. Inorg. Chem. 2013; 52: 6464
    CrossrefPubMed
  • 27 Wei Y, Zheng M, Chen L, Zhou X, Liu S. Dalton Trans. 2019; 48: 11763
    CrossrefPubMed
  • 28 Amemori S, Sasaki Y, Yanai N, Kimizuka N. J. Am. Chem. Soc. 2016; 138: 8702
    CrossrefPubMed