A novel photoreversible photochromic system involving a hydrogen transfer/cyclization sequence

Abstract

A novel photoreversible photochromic system, 3-(2-benzylbenzoyl)-1,2-R,R(1)-4(1H)-quinolinones/12-hydroxy-5-R-5a-R(1)-6-phenyl-5a,6-dihydrobenzo[b]acridin-11(5H)-ones, is described.

Wavelength-Dependent Reactivity of a Quinolinone: Toward a Photochromic Three-State System

“…On the other hand, irradiation of the derivative 2 did not lead to any enol but generated two stable diastereomeric cyclized structures. These photoisomers returned to the initial state under visible light irradiation, thus resulting in a two-state fully photoswitchable photochromic system. , These results paved the way for the design of multistate photoswitchable molecules within the quinolinone series.…”

Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

“…An interesting feature of the molecular structure is the presence of the intramolecular hydrogen bond C17-H17b/O2 (C/O distance 3.044 Å) analogous to the one observed in the 2-methyl derivative. 10 However, methylation of 10f, beside the target 3h, yielded two byproducts (Scheme 3), resulting from the substitution of the fluorine atom in position 5. The overall yield of the methylation products was 67e70% and the product ratio depended on the residual water concentration.…”

“…9 Further varying the structure of the quinolone derivatives afforded a new type of photochemically reversible and thermally stable photochromes based on 2-substituted 3-(2-benzylbenzoyl) derivatives. 10 The colored photoproducts, unlike those from furylfulgides 11 and dithienyl ethenes 12 , are fluorescent, which is important for non-destructive readout in information storage applications. It was noted that even minor variations of substituents at 2-position noticeably affect the photochromic behavior of 3-(2-benzylbenzoyl) derivatives.…”

Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones

“…The acyl-substituted 4-quinolones serve as valuable building blocks for the synthesis of bioactive molecules and color chemicals (Figure ). , In addition, they are readily transformed to structurally modified quinoline derivatives, which are ubiquitous in natural products and drugs. The frequently used methods for preparing 3-carbonyl-4-quinolones involve the thermal cyclization of β-anilinoacrylate derivatives prepared from the condensation of ethoxymethylene acetoacetate intermediates with anilines (the Gould–Jacobs reaction in pathway 1 of Scheme ) and the intramolecular ring closure of enaminoesters derived from reaction of β-ketonic enol ethers with methyl anthranilates (pathway 2) .…”