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  Bis-rhodamines bridged with a diazoketone linker: synthesis, structure, and photolysis

Shojaei, H., Bossi, M. L., Belov, V. N., & Hell, S. W. (2022). Bis-rhodamines bridged with a diazoketone linker: synthesis, structure, and photolysis. The Journal of Organic Chemistry, 87, 56-65. doi:10.1021/acs.joc.1c01721.

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Shojaei, Heydar1, Author           
Bossi, Mariano L., Author
Belov, V. N.1, Author                 
Hell, Stefan W.1, Author                 
Affiliations:
1Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society, ou_578627              

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Free keywords: Photodissociation ,Dyes and pigments, High-performance liquid chromatography, Mixtures, Molecular structure
 Abstract: Two fluorophores bound with a short photoreactive bridge are fascinating structures and remained unexplored. To investigate the synthesis and photolysis of such dyes, we linked two rhodamine dyes via a diazoketone bridge (−COCN2−) attached to position 5′ or 6′ of the pendant phenyl rings. For that, the mixture of 5′- or 6′-bromo derivatives of the parent dye was prepared, transformed into 1,2-diarylacetylenes, hydrated to 1,2-diarylethanones, and converted to diazoketones Ar1COCN2Ar2. The high performance liquid chromatography (HPLC) separation gave four individual regioisomers of Ar1COCN2Ar2. Photolysis of the model compound─C6H5COCN2C6H5─in aqueous acetonitrile at pH 7.3 and under irradiation with 365 nm light provided diphenylacetic acid amide (Wolff rearrangement). However, under the same conditions, Ar1COCN2Ar2 gave mainly α-diketones Ar1COCOAr2. The migration ability of the very bulky dye residues was low, and the Wolff rearrangement did not occur. We observed only moderate fluorescence increase, which may be explained by the insufficient quenching ability of diazoketone bridge (−COCN2−) and its transformation into another (weaker) quencher, 1,2-diarylethane-1,2-dione.

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Language(s): eng - English
 Dates: 2021-07-202021-12-172022
 Publication Status: Published in print
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.1c01721
 Degree: -

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Title: The 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: 87 Sequence Number: - Start / End Page: 56 - 65 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1