Multiple Addressing in a Hybrid Biphotochromic System

Frigoli, Michel; Mehl, Georg H.

doi:10.1002/ange.200462575

Angewandte Chemie

2005

DOI: 10.1002/ange.200462575

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Multiple Addressing in a Hybrid Biphotochromic System

Michel Frigoli

Georg H. Mehl

Abstract: Vier ungleiche Brüder: Ein aus einer Naphthopyran‐ und einer Diaryletheneinheit bestehendes biphotochromes System (1) bildet vier Zustände mit ganz unterschiedlichem Absorptionsverhalten. Das Öffnen des Naphthopyranrings hat Konjugation und elektronische Verknüpfung der beiden Photochrome zur Folge, das Schließen des offenen Diarylethensystems dehnt das π‐Elektronensystem über das ganze Molekül aus.

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Cited by 5 publications

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Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Liu

et al. 2019

Chemistry An Asian Journal

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Twot ypical molecular switches of spiropyran (SP) and benzoxazine (OX) were fused by sharing an indole to achieve an ew dual-addressable molecular switch (SP-OX-NO 2 ). Through properm olecular modification with NO 2 ,t he transformation from merocyanine (MC) to ring-closed SP or ring-closedO Xc an be controlled separately with visible light or base stimuli in solution,r espectively,a nd these processes are verifiedb yU V-vis and NMR spectroscopy as well as control experiments.T he cis-merocyanine( cis-MC) form is in-volved in the basochromic process in solution. DFT calculation suggests that the bidirectional switchingp roperty of the fused SP-OX molecular switch can be controlled separately,w hen the OX isomer is more stable than the deprotonated SP isomer.B ecause of the significant color variations in solution,t he simple dual-addressable switch has been further successfully appliedt oc onstruct am ulticolor reversible display on paper. Scheme1.Illustrationoft he design of the (a) linked dual-switchable system and the (b) fused dual-switchable molecule. (c) Photo-/ baso-chromisms of at ypical (c)nitrospiropyrana nd (d) oxazine. (e) Design and control of the transformation of SP-OX-NO 2 among its multiples tates.

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Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Liu

et al. 2019

Chemistry An Asian Journal

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A Multiaddressable Dyad with Switchable Cyan/Magenta/Yellow Colors for Full‐Color Rewritable Paper

Qin

Han

Geng

et al. 2018

Chemistry A European J

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Reversible multicolor displays on solid media created from single-molecule pigments are a long-awaited goal. Herein, a new and simple molecular dyad, which can undergo switchable cyan (C), magenta (M), and yellow (Y) color changes in both solution and the solid state upon exposure to light, water/acid, and nucleophiles, has been designed and synthesized. The stimuli used herein can be applied independent of each other, which is beneficial for color changes without mutual interference. For comparison, mixtures of the two molecular switching motifs that form the basis of the dyad were also studied. The dyad greatly outperforms the corresponding mixed system with respect to reversible color switching on the paper substrate. Its potential for full-color rewritable paper with excellent reversibility has been demonstrated. Legible multicolor prints, that is, high color contrast and resolution, good dispersion, and excellent reversibility, were achieved by using common water-jet and light-based printers. This work provides a very promising approach for the further development of full-color switchable molecules, materials, and displays.

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Synthesis of 2,2‐Disubstituted 2H‐Chromenes through Carbon‐Carbon Bond Formation Utilizing a [1,2]‐Phospha‐Brook Rearrangement under Brønsted Base Catalysis

Kondoh

Terada

2022

Chemistry A European J

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A new methodology for the synthesis of 2,2‐disubstituted 2H‐chromenes was developed by utilizing the [1,2]‐phospha‐Brook rearrangement under Brønsted base catalysis. Phosphazene P2‐tBu efficiently catalyzed the addition reaction of 4H‐chromen‐4‐ols containing a diethoxyphosphoryl group with α,β‐unsaturated ketones, which involved the catalytic generation of a carbanion through the [1,2]‐phospha‐Brook rearrangement and subsequent conjugate addition at the 2‐position to afford adducts possessing an alkenylphosphate moiety in a highly diastereoselective manner. Further transformation of the adducts based on a nickel‐catalyzed cross‐coupling reaction with arylzinc reagents provided densely functionalized 2,2‐disubstituted 2H‐chromenes.

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Multiple Addressing in a Hybrid Biphotochromic System

Cited by 5 publications

References 41 publications

Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

A Multiaddressable Dyad with Switchable Cyan/Magenta/Yellow Colors for Full‐Color Rewritable Paper

Synthesis of 2,2‐Disubstituted 2H‐Chromenes through Carbon‐Carbon Bond Formation Utilizing a [1,2]‐Phospha‐Brook Rearrangement under Brønsted Base Catalysis

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