Masahiro Irie - Diarylethene Molecular Photoswitches

4 Chapter 4Figure 4.1 A synthetic route of diarylethene 156having oligothiophene aryl ...Figure 4.2 Color changes of several diarylethene single crystals upon photoi...Scheme 4.1 Examples of diarylethene derivatives, which undergo photoswitchin...Figure 4.3 (a) Shape of single crystal 3and (b) directions of long ( x ) and ...Figure 4.4 Polarized absorption spectra of the red color in single crystal 3Figure 4.5 Photographs of single crystal 158under polarized light before ((...Figure 4.6 Polarized absorption spectra of colored single crystal 158(surfa...Figure 4.7 F o– F cdifference Fourier electron density maps for single cryst...Figure 4.8 ORTEP drawings of photoirradiated crystal 3. Black and red molecu...Figure 4.9 Molecular structures of the closed‐ring isomer 3c(a) generated i...Figure 4.10 Relationship between the photocyclization quantum yield and the ...Scheme 4.2 Dithienylethenes having anthracene substituents.Figure 4.11 (a) Three dithienylethenes 167, 4, and 20, which have similar si...Figure 4.12 (a) Molecular structure of 168. (b) ORTEP drawings and (c) molec...Figure 4.13 Photographs of single crystals of (a) 169oand (b) 170o. Top: ph...Figure 4.14 Patterned fluorescence photoswitching of single crystal 170o. (a...Figure 4.15 (a) Structures of open‐ and closed‐ring isomers of 5. (b) AFM im...Figure 4.16 Deformation of single crystals upon irradiation with UV (365 nm)...Figure 4.17 Molecular packing of open‐ring isomers of 1,2‐bis(2‐ethyl‐5‐phen...Figure 4.18 Chemical structures of open‐ and closed‐ring isomers of 1,2‐bis(...Figure 4.19 (a) Chemical structures of open‐ and closed‐ring isomers of 1,2‐...Figure 4.20 A shot of a tiny silica‐particle (∼100 μm) by crystal‐rod of 4u...Figure 4.21 (a) Chemical structures of component diarylethenes 172and 173i...Figure 4.22 (a) Photomechanical work of a molecular crystal cantilever made ...

5 Chapter 5Figure 5.1 (a) Fluorescence photoswitching of dyad 126upon alternate irradi...Figure 5.2 Histograms of (a–c) on time and (d–f) off time in PnBMA (a, d), P...Figure 5.3 A schematic diagram of the potential energy surfaces of a diaryle...Figure 5.4 Single‐molecule fluorescence photoswitching in a poly(methyl acry...Figure 5.5 Near‐field optical recording on an amorphous film of 178. Thickne...Figure 5.6 The images of an amorphous film of diarylethene 180irradiated wi...Figure 5.7 Holographic recording on a PMMA film containing 181based on a po...Figure 5.8 (a) Chemical structures of open‐ and closed‐ring isomers of 182. ...Scheme 5.1 Refractive index changes (Δ n ) of diarylethene derivatives at 817 ...

6 Chapter 6Figure 6.1 One‐way switching of conductance from the on state to the off sta...Figure 6.2 Photoswitching of conductance of diarylethene derivatives inserte...Figure 6.3 (a) A mixed self‐assembled monolayer, which incorporates dodecane...Figure 6.4 Configuration of the Mach–Zehnder modulator using diarylethene 13Figure 6.5 The open‐ring ( 191o) and closed‐ring ( 191c) isomers of radical‐su...Scheme 6.1 Open‐ring ( 192o) and closed‐ring ( 192c) isomers of radical‐substi...Scheme 6.2 Open‐ring ( 193o, 194o, 195o, 196o) and closed‐ring ( 193c, 194c, 1...Figure 6.6 ESR spectral changes for 193( n = 1) along with photoisomerizatio...Figure 6.7 Photoisomerization of diarylethene dyad 197upon photoirradiation...Figure 6.8 ESR spectra of (a) 197 (OO), (b) 197 (CO), and (c) 197 (CC).

7 Chapter 7Figure 7.1 (a) Schematic illustration of the fabrication procedure of the cr...Figure 7.2 Schematic illustration of the fabrication procedure of the crysta...Figure 7.3 (a) Selective metal deposition on the UV‐irradiated colored surfa...Figure 7.4 (a) μ‐Fuse and its operation. (b) Current–voltage characteristics...Figure 7.5 (a) Scheme of absorption modulation. Absorption at λ 1makes ...

8 Chapter 8Scheme 8.1 Examples of synthetic methods of polymers having diarylethene uni...Scheme 8.2 Synthesis of polymer p12by oxidation polymerization of diaryleth...Scheme 8.3 Selective photoreactions of polyurethanes p56containing two kind...Scheme 8.4 (a) Diarylethene dopants for liquid crystals. (b) A diarylethene ...

9 Chapter 9Figure 9.1 Two types (a and b) of structures of organic field‐effect transis...Scheme 9.1 Chemical structures of (a) polymeric and (b) small‐molecule semic...Figure 9.2 3D framework structures of photoresponsive metal organic framewor...Figure 9.3 The metal organic cage composed of two Pd 2+ions and four bis...Scheme 9.2 Turn‐on mode fluorescent diarylethene derivatives.Figure 9.4 Fatigue‐resistant property of sulfone derivatives of 1,2‐bis(2‐al...Figure 9.5 (a) Logarithmic plots of molar absorption coefficients of 8oin n ...Figure 9.6 RESOFT and confocal images of Vero cells. The line profiles of re...Figure 9.7 STORM images of Vero cells acquired (A) with and (B) without UV a...Figure 9.8 Fatigue resistance of diarylethene 216in an aqueous phosphate bu...Scheme 9.3 Rearrangement of positions of single and double bonds in (a) Diel...Scheme 9.4 The molecular design principle of photoresponsive polymers having...Scheme 9.5 Photocontrol of formation and scission of bonds using diarylethen...Scheme 9.6 Examples of biologically active diarylethene derivatives.Scheme 9.7 (a) Diarylethene crystal 3, which turned red upon γ‐rays irradiat...Figure 9.9 Fluorescence intensity increase upon γ‐irradiation. (a) Dependenc...