![2-[1-(4-Chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(6-quinolinyl)acetamide structure](https://static.chemtradehub.com/structs/501/501921-61-5-756a.webp "2-[1-(4-Chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(6-quinolinyl)acetamide structure")
2-[1-(4-Chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(6-quinolinyl)acetamide
CAS Number:
501921-61-5
Molecular Formula:
C26H18ClN3O2
Conversion of amino-terephthalonitriles to multi-substituted single benzene fluorophores with utility in bioimaging
Literature Information
Publication Date
2023-12-12
DOI
10.1039/D3OB01761C
Impact Factor
3.876
Authors
Tanya Raghava, Anjan Chattopadhyay, Nivedita Sarkar
View Original
Abstract
Substitution of two fluorine atoms of the tetrafluoroterephthalonitrile (TFTN) ring (ortho to each other) by amine nucleophiles through SNAr chemistry is achievable. However, tri- and tetra-substitution towards multi-substituted single benzene fluorophores (SBFs) is harder due to increased electron richness of the TFTN moiety. Tertiary amine donors promote the molecule towards such multi-substitution guided by the steric obstruction to intramolecular charge transfer to the TFTN ring. Contrarily, secondary amine substituents with better lone pair donation to the TFTN ring cannot induce the SNAr pathway and instead promote hydrolysis of the nitrile groups of the TFTN moiety. Theoretical investigations have helped unearth the reasons for this observed difference in chemical reactivities and also explain the differences in the emission spectra. Finally, the success of the synthetic method towards multi-substitution is showcased through creation of a highly lipophilic SBF bearing an octyl unit and demonstrating its utility in in vitro cellular imaging.
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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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