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  Impact of cyanine conformational restraint in the near-infrared range

Matikonda, S. S., Hammersley, G., Kumari, N., Grabenhorst, L., Glembockyte, V., Tinnefeld, P., et al. (2020). Impact of cyanine conformational restraint in the near-infrared range. The Journal of Organic Chemistry, 85(9), 5907-5915. doi:10.1021/acs.joc.0c00236.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000F-F790-7 Version Permalink: https://hdl.handle.net/21.11116/0000-000F-F791-6
Genre: Journal Article

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 Creators:
Matikonda, Siddharth S., Author
Hammersley, Gabrielle, Author
Kumari, Nikita, Author
Grabenhorst, Lennart, Author
Glembockyte, Viktorija1, Author           
Tinnefeld, Philip, Author
Ivanic, Joseph, Author
Levitus, Marcia, Author
Schnermann, Martin J., Author
Affiliations:
1Chemical Biology, Max Planck Institute for Medical Research, Max Planck Society, ou_2364732              

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 Abstract: Appending conformationally restraining ring systems to the cyanine chromophore creates exceptionally bright fluorophores in the visible range. Here, we report the application of this strategy in the near-infrared range through the preparation of the first restrained heptamethine indocyanine. Time-resolved absorption spectroscopy and fluorescence correlation spectroscopy verify that, unlike the corresponding parent unrestrained variant, the restrained molecule is not subject to photoisomerization. Notably, however, the room-temperature emission efficiency and the fluorescence lifetime of the restrained cyanine are not extended relative to the parent cyanine, even in viscous solvents. Thus, in contrast to prior reports, the photoisomerization of heptamethine cyanines does not contribute significantly to the excited-state chemistry of these molecules. We also find that the fluorescence lifetime of the restrained heptamethine cyanine is temperature-insensitive and significantly extended at moderately elevated temperatures relative to the parent cyanine. Finally, computational studies have been used to evaluate the impact of the conformational restraint on atomic and orbital structure across the cyanine series. These studies clarify the role of photoisomerization in the heptamethine cyanine scaffold and demonstrate the dramatic effect of restraint on the temperature sensitivity of these dyes.

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Language(s): eng - English
 Dates: 2020-01-302020-04-102020-05-01
 Publication Status: Issued
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: URI: https://pubmed.ncbi.nlm.nih.gov/32275153/
DOI: 10.1021/acs.joc.0c00236
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Title: The Journal of Organic Chemistry
  Other : Journal of Organic Chemistry
  Abbreviation : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 85 (9) Sequence Number: - Start / End Page: 5907 - 5915 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1