2‐Sulfanylhydroquinone Dimer as a Switchable Fluorescent Dye

Abstract

An ew dye was developed, the photoluminescence properties of which are controlled by ac hemical reaction. The fluorescencep roperties of 2-sulfanylhydroquinone dimers dependo nt he number of hydroxyl groups that are acylated. Unprotectedo rm onoacylated 2-sulfanylhydroquinone dimers displayed good fluorescencep roperties, where-as diacylateda nd tetraacylated 2-sulfanylhydroquinone dimers showedd ramatically decreased fluorescence. A monomesylated derivative was devised, which shows good fluorescencec haracteristics as as witching fluorescenced ye through achemical reaction.Scheme1.Preparation of O-acylated2 -sulfanylhydroquinone dimers.[a] Prof.Scheme2.Preparation of monomesylated 2-sulfanylhydroquionone dimer 7.Scheme3.Preparation of acylmesyl-2-hsulfanylhydroquinone dimers.

Development of Water Solubility of 2-Phenylsulfanylhydroquinone Dimer Dye

“…The preparation of the dye is very convenient, and large-scale synthesis is possible via a facile procedure. The presence of an electron-rich aromatic system enabled the control of fluorescence by the number of acyl groups introduced on the phenolic hydroxyl groups . The advantageous point of the dye is that the dye is expected to be a robust dye against pH and photoexcitation because it is based on a biaryl unit.…”

“…The presence of an electron-rich aromatic system enabled the control of fluorescence by the number of acyl groups introduced on the phenolic hydroxyl groups. 16 The advantageous point of the dye is that the dye is expected to be a robust dye against pH and photoexcitation because it is based on a biaryl unit. These properties make the 2-phenylsulfanylhydroquinone dimerderived dye a promising candidate for the detection and monitoring of chemical and biological events.…”