New mechanism, new chromophore: investigating the electrophilic behaviour of styrylindolium dyes. Issue 19 (29th April 2019)

• Record Type: Journal Article
• Authors: Perry, Alexis
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 19(2019)
• Page Start: 4825
• Page End: 4834
• Publication Date: 2019-04-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00641a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Deconvolution of sensor-analyte interactions in styrylindolium dyes led to the discovery of an unusual dearomatising 1, 8-addition of sulfur-centred nucleophiles. Abstract : 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.