A novel three-position molecular switch based on the transformations of a cyano-substituted pyrrol-2-one derivative

Abstract

The possibility of creating the first representative of a novel group of molecular switches sensitive to the solvent, to the action of acid-base reagents and to temperature changes has been...

High‐Contrast Optical Nitrile‐Rich Molecular Switches: Synthesis of Pyrrol‐2‐ones Containing a Butadienetricarbonitrile Fragment and Kinetics of Their Reversible Interaction with Morpholine

“…The stabilization of the spectral pattern after Et 3 N addition was associated with the impossibility of subsequent addition of this base to the anion of AM 1 type, which can be formed upon the addition of various amines. It should also be noted that the principal possibility of the formation of structures AM 1 from OTCP 1 a and triethylamine was described earlier [29] supporting the discussion above.…”

“…On the next step, electronic absorption spectra of chromophores 1 a – f in acetonitrile solution (50 μM) were recorded. The solvent was chosen due to the single report on reversible transformations of OTCP 1 a in acetonitrile [29] . The solutions of chromophores 1 a – f had an orange‐magenta color caused by an absorption band in the visible region of the spectrum centered at 494–512 nm (Figure 3, Table 2).…”

“…In this regard, herein, new nitrile‐rich compounds of the pyrrol‐2‐one (OTCP) series (Figure 1) bearing a BDTC fragment in the structure have been chosen as studying objects. It should be noted, that prior to this work, the single example of OTCP derivatives has been described only, [29] namely OTCP 1 a (Figure 2).…”

Thermoreversible Transformations of the Cyanosubstituted 2‐Oxopyrrole Derivative by the Action of Amines for the Creation of Novel High‐Contrast Coloration/Decoloration Systems

“…An analysis of the literature showed that one of the methods for the synthesis of 2‐oxopyrroles with an ylidenemalononitrile fragment in the third position is the use of corresponding pyrrole‐2,3‐diones in reaction with malononitrile [37,38] . In this regard, we carried out a sequence of transformations based on the initial reaction of available trimethylsilyl ether of propiophenone with oxalyl chloride leading to the formation of known furan‐2,3‐dione 3 [39] (Scheme 1).…”