5-Amino-1-(2,4-difluorophenyl)-3-methyl-1H-pyrazole-4-carbonitrile
CAS Number:
1020057-92-4
Molecular Formula:
C11H8F2N4
Divergent synthesis of 5′,7′-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores
Literature Information
Publication Date
2019-04-10
DOI
10.1039/C9OB00568D
Impact Factor
3.876
Authors
Shasha Zheng, Gu Lingyue, Michelle Jui Hsien Ong, Denis Jacquemin, Jean-Alexandre Richard, Rajavel Srinivasan
View Original
Abstract
We describe an expedient access to a 5′,6′,7′-trifluoro dihydroxanthene-hemicyanine fused scaffold in 2 steps and 54% overall yield from the corresponding salicylic aldehyde. A 6′-regioselective nucleophilic aromatic substitution (SNAr) reaction with a wide range of nitrogen, sulfur or selenium nucleophiles then gives access to 16 near-infrared (NIR) fluorophores emitting in the 710–750 nm range. We also report the experimental and theoretical photophysical investigations of these unique optical agents that include the first series of 6′-heavy atom substituted dihydroxanthenes, extending the pool of polyfluorinated markers for biomedical and material applications.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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