PDF herunterladen
Synlett 2020; 31(12): 1129-1134
DOI: 10.1055/s-0040-1707100
synpacts
© Georg Thieme Verlag Stuttgart · New York

One-Photon Upconversion-Like Photolysis: A New Strategy to Achieve Long-Wavelength Light-Excitable Photolysis

Wen Lv
a   Laboratory of Molecular Engineering and Nanomedicine, Dr. Li Dak-Sum Research Centre, The University of Hong Kong-Karolinska Institutet Collaboration in Regenerative Medicine, The University of Hong Kong, Hong Kong, P. R. of China
,
Weiping Wang  ∗
a   Laboratory of Molecular Engineering and Nanomedicine, Dr. Li Dak-Sum Research Centre, The University of Hong Kong-Karolinska Institutet Collaboration in Regenerative Medicine, The University of Hong Kong, Hong Kong, P. R. of China
b   Department of Pharmacology and Pharmacy, Li Ka Shing Faculty of Medicine, The University of Hong Kong, Hong Kong, P. R. of China   eMail: wangwp@hku.hk
› InstitutsangabenThis work was supported by Dr. Li Dak-Sum Research Fund (Start-up Fund) of The University of Hong Kong, Seed Fund for Basic Research of The University of Hong Kong (No. 201711159053), Guangdong-Hong Kong Technology Cooperation Funding Scheme (No. 2017A050506016), and Young Scientists Fund of the National Natural Science Foundation of China (No. 81803469).
Weitere Informationen

Publikationsverlauf

Received: 15. März 2020

Accepted after revision: 07. April 2020

Publikationsdatum:
20. Mai 2020 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

Photolysis reactions are widely utilized to release desired molecules under the control of light irradiation in the fields of photochemistry, biology, and drug delivery. In biological and medical applications, it is highly desired to increase the excitation wavelength for activating photolysis reactions, since the long-wavelength light (red or near-infrared light) has deep tissue penetration depth and low photocytotoxicity. Here, we briefly summarize current strategies of achieving long-wavelength light-excitable photolysis. We highlight our recently developed strategy of one-photon upconversion-like photolysis. Compared with the multiphoton upconversion-based photolysis, the one-photon strategy has a simpler energy transfer process and a higher ­energy utilization efficiency, providing a new path of activating photolysis reactions with increased excitation wavelength and photolysis quantum yield.

Key words

BODIPY - long-wavelength light excitation - photocleavable protecting groups - photocleavage - photon upconversion - red-shifted excitation - triplet-triplet annihilation - two-photon absorption
 

  • References

  • 1 Klán P, Šolomek T, Bochet CG, Blanc A, Givens R, Rubina M, Popik V, Kostikov A, Wirz J. Chem. Rev. 2013; 113: 119
    CrossrefPubMed
  • 2 Hansen MJ, Velema WA, Lerch MM, Szymanski W, Feringa BL. Chem. Soc. Rev. 2015; 44: 3358
    CrossrefPubMed
  • 3 Solomek T, Wirz J, Klan P. Acc. Chem. Res. 2015; 48: 3064
    CrossrefPubMed
  • 4 Pease AC, Solas D, Sullivan EJ, Cronin MT, Holmes CP, Fodor SP. A. Proc. Natl. Acad. Sci. U.S.A. 1994; 91: 5022
    CrossrefPubMed
  • 5 Geissler D, Antonenko YN, Schmidt R, Keller S, Krylova OO, Wiesner B, Bendig J, Pohl P, Hagen V. Angew. Chem. Int. Ed. 2005; 44: 1195
    CrossrefPubMed
  • 6 Xie C, Sun W, Lu H, Kretzschmann A, Liu J, Wagner M, Butt HJ, Deng X, Wu S. Nat. Commun. 2018; 9: 3842
    CrossrefPubMed
  • 7 Hansen MJ, Feringa FM, Kobauri P, Szymanski W, Medema RH, Feringa BL. J. Am. Chem. Soc. 2018; 140: 13136
    CrossrefPubMed
  • 8 Lemke EA, Summerer D, Geierstanger BH, Brittain SM, Schultz PG. Nat. Chem. Biol. 2007; 3: 769
    CrossrefPubMed
  • 9 Li Y, Zhang Y, Wang W. Nano Res. 2018; 11: 5424
    Crossref
  • 10 Ruskowitz ER, DeForest CA. Nat. Rev. Mater. 2018; 3: 17087
    Crossref
  • 11 Hou Y, Zhou Z, Huang K, Yang H, Han G. ChemPhotoChem 2018; 2: 1005
    Crossref
  • 12 Goswami PP, Syed A, Beck CL, Albright TR, Mahoney KM, Unash R, Smith EA, Winter AH. J. Am. Chem. Soc. 2015; 137: 3783
    CrossrefPubMed
  • 13 Slanina T, Shrestha P, Palao E, Kand D, Peterson JA, Dutton AS, Rubinstein N, Weinstain R, Winter AH, Klán P. J. Am. Chem. Soc. 2017; 139: 15168
    CrossrefPubMed
  • 14 Peterson JA, Wijesooriya C, Gehrmann EJ, Mahoney KM, Goswami PP, Albright TR, Syed A, Dutton AS, Smith EA, Winter AH. J. Am. Chem. Soc. 2018; 140: 7343
    CrossrefPubMed
  • 15 Zhou J, Liu Q, Feng W, Sun Y, Li F. Chem. Rev. 2015; 115: 395
    CrossrefPubMed
  • 16 Kobayashi H, Ogawa M, Alford R, Choyke PL, Urano Y. Chem. Rev. 2010; 110: 2620
    CrossrefPubMed
  • 17 Aujard I, Benbrahim C, Gouget M, Ruel O, Baudin JB, Neveu P, Jullien L. Chem. Eur. J. 2006; 12: 6865
    CrossrefPubMed
  • 18 Suzuki AZ, Watanabe T, Kawamoto M, Nishiyama K, Yamashita H, Ishii M, Iwamura M, Furuta T. Org. Lett. 2003; 5: 4867
    CrossrefPubMed
  • 19 Lin Q, Yang L, Wang Z, Hua Y, Zhang D, Bao B, Bao C, Gong X, Zhu L. Angew. Chem. Int. Ed. 2018; 57: 3722
    CrossrefPubMed
  • 20 Bojtár M, Kormos A, Kis-Petik K, Kellermayer M, Kele P. Org. Lett. 2019; 21: 9410
    CrossrefPubMed
  • 21 Fournier L, Aujard I, Saux TL, Maurin S, Beaupierre S, Baudin JB, Jullien L. Chem. Eur. J. 2013; 19: 17494
    CrossrefPubMed
  • 22 Gandioso A, Cano M, Massaguer A, Marchán V. J. Org. Chem. 2016; 81: 11556
    CrossrefPubMed
  • 23 Kowada T, Maeda H, Kikuchi K. Chem. Soc. Rev. 2015; 44: 4953
    CrossrefPubMed
  • 24 Loudet A, Burgess K. Chem. Rev. 2007; 107: 4891
    CrossrefPubMed
  • 25 Lu H, Mack J, Yang Y, Shen Z. Chem. Soc. Rev. 2014; 43: 4778
    CrossrefPubMed
  • 26 Zhao J, Xu K, Yang W, Wang Z, Zhong F. Chem. Soc. Rev. 2015; 44: 8904
    CrossrefPubMed
  • 27 Li MD, Wong NK, Xiao J, Zhu R, Wu L, Dai SY, Chen F, Huang G, Xu L, Bai X, Geraskina MR, Winter AH, Chen X, Liu Y, Fang W, Yang D, Phillips DL. J. Am. Chem. Soc. 2018; 140: 15957
    CrossrefPubMed
  • 28 Matsuzaki M, Hayama T, Kasai H, Ellis-Davies GC. R. Nat. Chem. Biol. 2010; 6: 255
    CrossrefPubMed
  • 29 Zhao L, Peng J, Huang Q, Li C, Chen M, Sun Y, Lin Q, Zhu L, Li F. Adv. Funct. Mater. 2014; 24: 363
    Crossref
  • 30 Wang W, Liu Q, Zhan C, Barhoumi A, Yang T, Wylie RG, Armstrong PA, Kohane DS. Nano Lett. 2015; 15: 6332
    CrossrefPubMed
  • 31 Liu Q, Wang W, Zhan C, Yang T, Kohane DS. Nano Lett. 2016; 16: 4516
    CrossrefPubMed
  • 32 Huang L, Zhao Y, Zhang H, Huang K, Yang J, Han G. Angew. Chem. Int. Ed. 2017; 56: 14400
    CrossrefPubMed
  • 33 Lv W, Li Y, Li F, Lan X, Zhang Y, Du L, Zhao Q, Phillips DL, Wang W. J. Am. Chem. Soc. 2019; 141: 17482
    CrossrefPubMed