New mechanism, new chromophore: investigating the electrophilic behaviour of styrylindolium dyes

文献情報

出版日 2019-04-26

DOI 10.1039/C9OB00641A

インパクトファクター 3.876

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要旨

To inform the design of future merocyanine-based sensors for nucleophilic analytes, a range of model styrylindolium salts were synthesised, and their behaviour towards cyanide, methanethiolate and sulfide was examined using spectroscopic techniques. In the majority of cases, standard 1,2- and 1,4-nucleophilic additions predominated; however, 4-nitrostyrylindolium salts underwent an unexpected dearomatising 1,8-addition with sulfur-centred nucleophiles. The enamine triene products thus produced display useful optical properties and provide a platform for novel sensor design, and the unusual 1,8-reaction pathway enables synthesis of novel molecular architecture.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 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.

New mechanism, new chromophore: investigating the electrophilic behaviour of styrylindolium dyes

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