Highlights of metal ion-based photochemical switches

Abstract Selected metal complexes behaving as photochemical switches, mostly operating by light emission/absorption without the intervention of any added chemical species, are reviewed. First, the switching mechanisms are analyzed to offer readers an easier understanding of the described systems. Examples of photochemical switching based on complexation/decomplexation processes and photo-bistable systems, comprising metal complexes with azobenzene, azopyridine, diarylethene, spirocyclic and rhodamine ligands, make the central body of the review. These examples were chosen to provide an overview of the evolution of metal-ion based photochemical switches, collecting together historical cases and more recent systems mainly reported in the last 15 years.

[1]  H. Tian,et al.  A dual-ion-switched molecular brake based on ferrocene. , 2009, Chemical communications.

[2]  V. Yam,et al.  Tetranuclear Macrocyclic Gold(I) Alkynyl Phosphine Complex Containing Azobenzene Functionalities: A Dual-Input Molecular Logic with Photoswitching Behavior Controllable via Silver(I) Coordination/Decoordination , 2007 .

[3]  N. Tamai,et al.  Photoluminescence switching of azobenzene-conjugated Pt(II) terpyridine complexes by trans-cis photoisomerization. , 2002, Inorganic chemistry.

[4]  R. Winter,et al.  Ruthenium stilbenyl and diruthenium distyrylethene complexes: aspects of electron delocalization and electrocatalyzed isomerization of the Z-isomer. , 2012, Journal of the American Chemical Society.

[5]  Rong-Hua Yang,et al.  A spiropyran-based ensemble for visual recognition and quantification of cysteine and homocysteine at physiological levels. , 2006, Angewandte Chemie.

[6]  A. Bianchi,et al.  Binding of H+ and Zn(II) ions with a new fluorescent macrocyclic phenanthrolinophane. , 2010, Dalton transactions.

[7]  H. Tian,et al.  Photochromic bisthienylethene as multi-function switches. , 2007, Chemical communications.

[8]  H. Wynberg,et al.  Photochemically induced cyclization of some furyl- and thienylethenes , 1967 .

[9]  Zhenan Bao,et al.  Syntheses, characterization, and photochromic studies of spirooxazine-containing 2,2'-bipyridine ligands and their zinc(II) thiolate complexes. , 2008, Inorganic chemistry.

[10]  He Tian,et al.  Reversible near-infrared fluorescence switch by novel photochromic unsymmetrical-phthalocyanine hybrids based on bisthienylethene. , 2002, Chemical communications.

[11]  S. Nagao,et al.  DNA cleavage by the photocontrolled cooperation of Zn(II) centers in an azobenzene-linked dizinc complex. , 2011, Inorganic chemistry.

[12]  T. Arai,et al.  Synthesis and photochemical properties of porphyrin–azobenzene triad , 2004 .

[13]  R. H. Mitchell,et al.  Cobalt Complexes Containing Dimethyldihydropyrene-Substituted Cyclobutadiene Ligands , 2011 .

[14]  S. Shinkai,et al.  Photoresponsive Crown Ethers. 9. Cylindrical and Phane Crown Ethers with Azobenzene Segments as a Light-switch Functional Group , 1983 .

[15]  Q. Guo,et al.  Optical switching and fluorescence modulation properties of photochromic dithienylethene derivatives , 2007 .

[16]  P. Matousek,et al.  Ultrafast excited-state dynamics preceding a ligand trans-cis isomerization of fac-[Re(Cl)(CO)3(t-4-styrylpyridine)2] and fac-[Re(t-4-styrylpyridine)(CO)3(2,2'-bipyridine)]+. , 2005, The journal of physical chemistry. A.

[17]  He Tian,et al.  Recent progresses on diarylethene based photochromic switches. , 2004, Chemical Society reviews.

[18]  M. Sugimoto,et al.  Photo-controllable tristability of a dithiolato-bipyridine-Pt(II) complex molecule containing two azobenzene moieties. , 2005, Chemical communications.

[19]  Bing Yin,et al.  A novel rhodamine-based fluorescent and colorimetric “off–on” chemosensor and investigation of the recognizing behavior towards Fe3+ , 2012 .

[20]  C. Lodeiro,et al.  Photochemical- and pH-switching Properties of a New Photoelastic Ligand Based Upon Azobenzene. Basicity and Anion Binding , 2001 .

[21]  M. Sukwattanasinitt,et al.  Comparative study of azobenzene and stilbene bridged crown ether p - tert -butylcalix[4]arene , 2005 .

[22]  David C. Magri,et al.  ‘Pourbaix sensors’: a new class of fluorescent pE–pH molecular AND logic gates based on photoinduced electron transfer , 2013 .

[23]  A. Lees,et al.  Photoswitchable trinuclear transition-metal complexes. Intramolecular triplet–triplet energy transfer from fac-(diimine)ReI(CO)3 chromophores to a stilbene-like bridging ligand , 2000 .

[24]  H. Nishihara,et al.  Novel photoisomerization behavior of Rh binuclear complexes involving an azobenzene-bridged bis(terpyridine) ligand. Strong effects of counterion and solvent and the induction of redox potential shift. , 2000, Inorganic chemistry.

[25]  L. De Cola,et al.  Photochromic dithienylethene derivatives containing Ru(II) or Os(II) metal units. Sensitized photocyclization from a triplet state. , 2004, Inorganic chemistry.

[26]  Alvaro Fernandez-Acebes,et al.  Optical Switching and Fluorescence Modulation in Photochromic Metal Complexes , 1998 .

[27]  V. Yam,et al.  A Photochromic Platinum(II) Bis(alkynyl) Complex Containing a Versatile 5,6-Dithienyl-1,10-phenanthroline , 2007 .

[28]  M. Boillot,et al.  Ligand-Driven Light-Induced Spin Change in Transition-Metal Complexes: Selection of an Appropriate System and First Evidence of the Effect, in Fe(II)(4-styrylpyridine)(4)(NCBPh(3))(2). , 1996, Inorganic chemistry.

[29]  H. Tian,et al.  Soft mimic gear-shift with a multi-stimulus modified diarylethene , 2009 .

[30]  R. Perutz,et al.  Proton-controlled photoisomerization: rhenium(I) tricarbonyl bipyridine linked to amine or azacrown ether groups by a styryl pyridine bridging ligand , 2000 .

[31]  A. O. Patrocinio,et al.  Excited-state dynamics in fac-[Re(CO)3(Me4phen)(L)]+. , 2010, The journal of physical chemistry. A.

[32]  C. Lodeiro,et al.  Switching from intramolecular energy transfer to intramolecular electron transfer by the action of pH and Zn2+ co-ordination , 2002 .

[33]  H. Nishihara,et al.  Photo- and Proton-Coupled Isomerization of Novel Azo-Conjugated Platinadithiolene Complex , 2001 .

[34]  Helmut Görner,et al.  Photochromism of nitrospiropyrans: effects of structure, solvent and temperature , 2001 .

[35]  S. Tsuchiya.  Intramolecular Electron Transfer of Diporphyrins Comprised of Electron-Deficient Porphyrin and Electron-Rich Porphyrin with Photocontrolled Isomerization , 1999 .

[36]  Steven L. Murov,et al.  Handbook of photochemistry , 1973 .

[37]  N. Turro,et al.  Principles of Molecular Photochemistry: An Introduction , 2008 .

[38]  Hiromasa Nishikiori,et al.  Photochromic behavior of spironaphthoxazine in metal ion-containing solutions , 2011 .

[39]  T. Aida,et al.  Mechanical twisting of a guest by a photoresponsive host , 2006, Nature.

[40]  D. Qu,et al.  Dual-mode control of PET process in a ferrocene-functionalized [2]rotaxane with high-contrast fluorescence output. , 2012, Organic letters.

[41]  Seiji Shinkai,et al.  Photoresponsive crown ethers. Part 6. Ion transport mediated by photoinduced cis—trans interconversion of azobis(benzocrown ethers) , 1982 .

[42]  N. McClenaghan,et al.  Photolariats: synthesis, metal ion complexation and photochromism , 2012 .

[43]  G. Haberhauer,et al.  A molecular four-stroke motor. , 2011, Angewandte Chemie.

[44]  Dermot Diamond,et al.  Spiropyran-based reversible, light-modulated sensing with reduced photofatigue , 2009 .

[45]  H. Nishihara,et al.  Reversible photochromism of a ferrocenylazobenzene monolayer controllable by a single green light source. , 2007, Chemical communications.

[46]  James T. C. Wojtyk,et al.  Effects of metal ion complexation on the spiropyran–merocyanine interconversion: development of a thermally stable photo-switch , 1998 .

[47]  H. Santos,et al.  Light and colour as analytical detection tools: a journey into the periodic table using polyamines to bio-inspired systems as chemosensors. , 2010, Chemical Society reviews.

[48]  V. Yam,et al.  Syntheses, luminescence switching, and electrochemical studies of photochromic dithienyl-1,10-phenanthroline zinc(II) bis(thiolate) complexes. , 2007, Inorganic chemistry.

[49]  K. Teshima,et al.  Chelation ability of spironaphthoxazine with metal ions in silica gel , 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[50]  H. Nishihara,et al.  A Large Trans/cis Conversion Ratio In Redox-Conjugated Single-Light Reversible Isomerization of a Cobalt Complex with meta-Bipyridylazobenzene Ligands , 2002 .

[51]  H. Nishihara,et al.  Reversible light-induced magnetization change in an azobenzene-attached pyridylbenzimidazole complex of iron(II) at room temperature. , 2009, Dalton transactions.

[52]  Guo-Li Shen,et al.  Highly sensitive and selective colorimetric and off-on fluorescent chemosensor for Cu2+ in aqueous solution and living cells. , 2009, Analytical chemistry.

[53]  A. Louie,et al.  Photochromically-controlled, reversibly-activated MRI and optical contrast agent. , 2007, Chemical communications.

[54]  M. Yamashita,et al.  Coordination assemblies of [Mn4] single-molecule magnets linked by photochromic ligands: photochemical control of the magnetic properties. , 2009, Journal of the American Chemical Society.

[55]  R. Jukes,et al.  Electronic energy transfer in a dinuclear Ru/Os complex containing a photoresponsive dithienylethene derivative as bridging ligand , 2005 .

[56]  T. Deligeorgiev,et al.  Effect of complexation on the photochromism of 5'-(benzothiazol-2-yl)spiroindolinonaphthooxazines in polar solvents , 2005 .

[57]  Manoj K. Kesharwani,et al.  Ratiometric detection of Cr3+ and Hg2+ by a naphthalimide-rhodamine based fluorescent probe. , 2012, Inorganic chemistry.

[58]  T. B. Norsten,et al.  Nondestructive Data Processing Based on Chiroptical 1,2-Dithienylethene Photochromes , 2001 .

[59]  Ki‐Min Park,et al.  A Highly Hg(II)-selective Chemosensor with Unique Diarylethene Fluorophore , 2010 .

[60]  Tatsuya Kato,et al.  Photo-reversible Pb2+-complexation of insoluble poly(spiropyran methacrylate-co-perfluorohydroxy methacrylate) in polar solvents. , 2003, Chemical communications.

[61]  N. Branda,et al.  Photomodulation of Lewis basicity in a pyridine-functionalized 1,2-dithienylcyclopentene. , 2005, Chemical communications.

[62]  A. Credi,et al.  Redox control of molecular motion in switchable artificial nanoscale devices. , 2011, Antioxidants & redox signaling.

[63]  M. Maekawa,et al.  Reversible photochromism of novel silver(I) coordination complexes with 1,2-bis(2′-methyl-5′-(2″-pyridyl)-3′-thienyl)perfluorocyclopentene in crystalline phase , 2006 .

[64]  S. Shinkai,et al.  Photoresponsive crown ethers. 8. Azobenzenophane-type switched-on crown ethers which exhibit an all-or-nothing change in ion-binding ability , 1983 .

[65]  C. Lodeiro,et al.  Water-soluble Fluorescent Chemosensors: in Tune with Protons , 2007 .

[66]  L. R. Sousa,et al.  Crown ether model systems for the study of photoexcited state response to geometrically oriented perturbers. The effect of alkali metal ions on emission from naphthalene derivatives , 1977 .

[67]  Y. Hirahara,et al.  Photo-reversible and selective Cu2+ complexation of a spiropyran-carrying sulfobetaine copolymer in saline solution , 2010 .

[68]  H. Nishihara,et al.  Photoisomerization-induced Change in the Size of Ferrocenylazobenzene-attached Dendrimers , 2006 .

[69]  D. Diamond,et al.  Polystyrene bead-based system for optical sensing using spiropyran photoswitches , 2008 .

[70]  V. Yam,et al.  Metal coordination-assisted near-infrared photochromic behavior: a large perturbation on absorption wavelength properties of N,N-donor ligands containing diarylethene derivatives by coordination to the rhenium(I) metal center. , 2007, Journal of the American Chemical Society.

[71]  K. Matsuda,et al.  Photochromism of metal complexes composed of diarylethene ligands and Zn(II), Mn(II), and Cu(II) hexafluoroacetylacetonates. , 2004, Inorganic chemistry.

[72]  H. Nishihara,et al.  Coordination-synchronized trans-cis photoisomerization of bipyridylazobenzene driven by a Cu(II)/Cu(I) redox change. , 2003, Inorganic chemistry.

[73]  Y. Kondo,et al.  Photoregulated-metal binding with an azobenzene-capped calix[4]arene , 1995 .

[74]  K. Ghosh,et al.  A rhodamine appended tripodal receptor as a ratiometric probe for Hg2+ ions. , 2012, Organic & biomolecular chemistry.

[75]  H. Nishihara,et al.  Synthesis of photo-switchable 3-FcAB-modified polymer particles , 2011 .

[76]  S. Shinkai,et al.  Photoresponsive crown ethers. Part 7. Proton and metal ion catalyses in the cis—trans isomerisation of azopyridines and an azopyridine-bridged cryptand , 1982 .

[77]  H. Nishihara,et al.  Synthesis of azo-conjugated metalladithiolenes and their photo- and proton-responsive isomerization reactions. , 2003, Journal of the American Chemical Society.

[78]  Zhen Jin,et al.  Bifunctional fluoroionphore-ionic liquid hybrid for toxic heavy metal ions: improving its performance via the synergistic extraction strategy. , 2012, Analytical chemistry.

[79]  M. Irie,et al.  Alkali metal ion effect on the photochromism of 1,2-bis(2,4-dimethylthien-3-yl)-perfluorocyclopentene having benzo-15-crown-5 moieties , 1998 .

[80]  J. Etxebarria,et al.  Azo isocyanide gold(i) liquid crystals, highly birefringent and photosensitive in the mesophase. , 2009, Inorganic chemistry.

[81]  S. Shinkai,et al.  Photoresponsive crown ethers. Part 18. Photochemically ‘switched-on’ crown ethers containing an intra-annular azo substituent and their application to membrane transport , 1987 .

[82]  Masahiro Irie,et al.  Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives , 1988 .

[83]  C. Wilcox,et al.  Precipitons-Functional Protecting Groups to Facilitate Product Separation: Applications in Isoxazoline Synthesis. , 2001, Angewandte Chemie.

[84]  S. Hirota,et al.  Photocontrol of spatial orientation and DNA cleavage activity of copper(II)-bound dipeptides linked by an azobenzene derivative. , 2008, Inorganic chemistry.

[85]  Heidi Blattmann,et al.  Über die phototropie des trans-15,16-dimethyldihydropyrens und seiner derivate , 1970 .

[86]  Eunkyoung Kim,et al.  Synthesis and photochromic reactivity of macromolecules incorporating four dithienylethene units , 2005 .

[87]  X. Bu,et al.  Ratiometric and selective fluorescent sensor for Zn2+ as an "off-on-off" switch and logic gate. , 2012, Inorganic Chemistry.

[88]  Z. Tao,et al.  New fluorescent sensor for antimony and transition metal cations based on rhodamine amide-arm homotrioxacalix[3]arene , 2010 .

[89]  H. Nishihara,et al.  Synthesis and Physical Properties of a π-Conjugated Ruthenium(II) Dinuclear Complex Involving an Azobenzene-Bridged Bis(terpyridine) Ligand , 2000 .

[90]  Masahiro Irie,et al.  Diarylethenes for Memories and Switches. , 2000, Chemical reviews.

[91]  A. P. Silva,et al.  Fluorescent signalling crown ethers; ‘switching on’ of fluorescence by alkali metal ion recognition and binding in situ , 1986 .

[92]  S. Shinkai,et al.  On–off-switched crown ether–metal ion complexation by photoinduced intramolecular ammonium group ‘tail-biting’ , 1984 .

[93]  M. Shimomura,et al.  PHOTOISOMERIZATION OF AZOBENZOCROWN ETHERS. EFFECT OF COMPLEXATION OF ALKALINE EARTH METAL IONS , 1997 .

[94]  N. Tamai,et al.  Synthesis, characterization, and photochemical properties of azobenzene-conjugated Ru(II) and Rh(III) bis(terpyridine) complexes. , 2001, Inorganic chemistry.

[95]  Kazushi Suzuki,et al.  Photochromic behavior of a bisthienylethene bearing Cu(I)-1,10-phenanthroline complexes , 2012 .

[96]  K. Matsuda,et al.  Photochromism of metal complexes composed of diarylethene ligands and ZnCl2. , 2004, Inorganic chemistry.

[97]  Maurizio Licchelli,et al.  Transition Metals as Switches , 1999 .

[98]  M. Sugimoto,et al.  trans-cis photoisomerization of azobenzene-conjugated dithiolato-bipyridine platinum(II) complexes: extension of photoresponse to longer wavelengths and photocontrollable tristability. , 2009, Chemistry.

[99]  Hok-Lai Wong,et al.  Photochromic alkynes as versatile building blocks for metal alkynyl systems: design, synthesis, and photochromic studies of diarylethene-containing platinum(II) phosphine alkynyl complexes. , 2011, Inorganic chemistry.

[100]  Takayuki Matsuda,et al.  Synthesis of Azo-Bridged Ferrocene Oligomers and a Polymer and Electrochemical and Optical Analysis of Internuclear Electronic Interactions in Their Mixed-Valence States. , 1999, Inorganic chemistry.

[101]  B. Feringa,et al.  Combining organic photochromism with inorganic paramagnetism--optical tuning of the iron(II) electronic structure. , 2008, Dalton transactions.

[102]  N. Reynier,et al.  Complexation properties of a new photosensitive calix[4]arene crown ether containing azo unit in the lower rim towards alkali cations , 1998 .

[103]  H. Nishihara,et al.  A ferrocenylspiropyran that functions as a molecular photomemory with controllable depth. , 2006, Angewandte Chemie.

[104]  S. Ibeas,et al.  Chromogenic and fluorogenic detection of cations in aqueous media by means of an acrylic polymer chemosensor with pendant Rhodamine-based dyes , 2013 .

[105]  R. Kutta,et al.  Design and photoinduced surface relief grating formation of photoresponsive azobenzene based molecular materials with ruthenium acetylides , 2010 .

[106]  Hok-Lai Wong,et al.  Diarylethene-containing cyclometalated platinum(II) complexes: tunable photochromism via metal coordination and rational ligand design. , 2011, Journal of the American Chemical Society.

[107]  J. Malval,et al.  Photoswitching of cation complexation with A monoaza-crown dithienylethene photochrome. , 2002, Journal of the American Chemical Society.

[108]  N. Tamai,et al.  Photochemical behavior of azobenzene-conjugated CoII, CoIII, and FeII bis(terpyridine) complexes. , 2003, Inorganic chemistry.

[109]  W. Brittain,et al.  Use of Precipitons for Copper Removal in Atom Transfer Radical Polymerization , 2002 .

[110]  L. De Cola,et al.  Photophysical and redox properties of dinuclear Ru and Os polypyridyl complexes with incorporated photostable spiropyran bridge. , 2009, Inorganic chemistry.

[111]  K. Furuichi,et al.  Reversible Photochromism of a Crystalline Dithienylethene Copper(I) Polymer , 1996 .

[112]  Jean-Pierre Launay,et al.  Synthesis and Properties of Dinuclear Complexes with a Photochromic Bridge: An Intervalence Electron Transfer Switching “On” and “Off” , 2000 .

[113]  W. Schmidt.  Die Valenzisomerisierung des trans‐15, 16‐Dimethyl‐dihydropyrens ‐ ein beitrag zur frage nach der aktivierungsenergie symmetrie‐verbotener prozesse. Vorläufige mitteilung , 1971 .

[114]  M. Irie,et al.  Photoresponsive Tweezers for Alkali Metal Ions. Photochromic Diarylethenes Having Two Crown Ether Moieties , 1998 .

[115]  G. Collins,et al.  Selective metals determination with a photoreversible spirobenzopyran. , 1999, Analytical chemistry.

[116]  O. Fedorova,et al.  Spiropyran, chromene or spirooxazine ligands: Insights into mutual relations between complexing and photochromic properties , 2011 .

[117]  A. Lees,et al.  Self-assembly of transition-metal-based macrocycles linked by photoisomerizable ligands: examples of photoinduced conversion of tetranuclear-dinuclear squares. , 2002, Inorganic chemistry.

[118]  M. Hara,et al.  A reversibly photoswitchable mononuclear palladium(II) complex with ortho-diethylated azobenzene ligands , 2010 .

[119]  Dan Ouyang,et al.  Theoretical study of crown ethers with incorporated azobenzene moiety , 2012, Journal of Molecular Modeling.

[120]  S. Carli,et al.  Triplet pathways in diarylethene photochromism: photophysical and computational study of dyads containing ruthenium(II) polypyridine and 1,2-bis(2-methylbenzothiophene-3-yl)maleimide units. , 2008, Journal of the American Chemical Society.

[121]  Jason Locklin,et al.  Reversible colorimetric ion sensors based on surface initiated polymerization of photochromic polymers. , 2008, Chemical communications.

[122]  A. Lees,et al.  Photoswitching tetranuclear rhenium(I) tricarbonyl diimine complexes with a stilbene-like bridging ligand. , 2011, Chemical communications.

[123]  T. B. Norsten,et al.  Photoswitching of stereoselectivity in catalysis using a copper dithienylethene complex. , 2005, Angewandte Chemie.

[124]  Françisco M Raymo,et al.  Optical processing with photochromic switches. , 2006, Chemistry.

[125]  K. Schanze,et al.  Photophysics and Photochemistry of Stilbene-Containing Platinum Acetylides , 2004 .

[126]  J. Otsuki,et al.  Molecular switches for electron and energy transfer processes based on metal complexes , 2008 .

[127]  Kang Sun,et al.  Resettable, multi-readout logic gates based on controllably reversible aggregation of gold nanoparticles. , 2011, Angewandte Chemie.

[128]  D. Whitten,et al.  Photochemistry of ruthenium complexes. Ligand isomerization via orbitally different excited states , 1971 .

[129]  S. Shinkai,et al.  Photoresponsive Crown Ethers. 1. Cis-Trans Isomerism of Azobenzene as a Tool to Enforce Conformational-Changes of Crown Ethers and Polymers , 1980 .

[130]  Fushi Zhang,et al.  Photoswitching of the third-order nonlinear optical properties of azobenzene-containing phthalocyanines based on reversible host–guest interactions , 2009 .

[131]  Anthony W. Czarnik,et al.  Chelation enhanced fluorescence in 9,10-bis[[(2-(dimethylamino)ethyl)methylamino]methyl]anthracene , 1988 .

[132]  V. Yam,et al.  Synthesis, Characterization, and Photoisomerization Studies of Azo- and Stilbene-Containing Surfactant Rhenium(I) Complexes , 2001 .

[133]  H. Nishihara,et al.  Reversible trans-cis photoisomerization of azobenzene-attached bipyridine ligands coordinated to cobalt using a single UV light source and the Co(III)/Co(II) redox change. , 2001, Chemical communications.

[134]  H. Gray,et al.  Photoswitchable luminescence of rhenium(i) tricarbonyl diimines. , 2004, Inorganic chemistry.

[135]  Y. Einaga,et al.  Reversible photocontrol of molecular assemblies of metal complex containing azo-amphiphiles , 2005 .

[136]  H. Nishihara.  Multi-Mode Molecular Switching Properties and Functions of Azo-Conjugated Metal Complexes , 2004 .

[137]  Hyunbong Choi,et al.  Selective photoswitching of a dyad with diarylethene and spiropyran units , 2005 .

[138]  He Tian,et al.  Novel bisthienylethene-based photochromic tetraazaporphyrin with photoregulating luminescence , 2002 .

[139]  Daoben Zhu,et al.  Photomodulation of the electrode potential of a photochromic spiropyran-modified Au electrode in the presence of Zn2+: a new molecular switch based on the electronic transduction of the optical signals. , 2006, Chemical communications.

[140]  A. Lees,et al.  Synthesis, Photophysical Properties, and Photoinduced Luminescence Switching of Trinuclear Diimine Rhenium(I) Tricarbonyl Complexes Linked by an Isomerizable Stilbene-like Ligand , 2002 .

[141]  M. Inouye,et al.  Alkali metal recognition induced isomerization of spiropyrans , 1990 .

[142]  Anthony W. Czarnik,et al.  Chemical Communication in Water Using Fluorescent Chemosensors , 1994 .

[143]  K. Kimura,et al.  AFM Observation of Stimuli-Responsive Stretching Behavior for Spirobenzopyran/Crown-Ether Copolymer , 2011 .

[144]  K. Matsuda,et al.  Single-crystalline photochromism of a linear coordination polymer composed of 1,2-bis[2-methyl-5-(4-pyridyl)-3-thienyl]perfluorocyclopentene and bis(hexafluoroacetylacetonato)zinc(II) , 2001 .

[145]  G. Marriott,et al.  Optically switchable chelates: optical control and sensing of metal ions. , 2008, The Journal of organic chemistry.

[146]  P. G. Sammes,et al.  Synthesis of Some New Substituted Photochromic N,N′‐Bis(spiro[1‐benzopyran‐2,2′‐indolyl])diazacrown Systems with Substituent Control over Ion Chelation , 2006 .

[147]  A. K. Clark,et al.  Ferrocenylazobenzenes. Resonance Interaction of Ferrocene with Substrates , 1960 .

[148]  K. Kamada,et al.  Synthesis and photochromism of spirobenzopyran derivatives bearing an oxymethylcrown ether moiety: metal ion-induced switching between positive and negative photochromisms. , 2001, The Journal of organic chemistry.

[149]  Ka-Ho Leung,et al.  Recent advances in luminescent heavy metal complexes for sensing , 2012 .

[150]  Kenji Matsuda,et al.  Photoswitching of the magnetic interaction between a copper(II) ion and a nitroxide radical by using a photochromic spin coupler. , 2003, Chemistry.

[151]  H. Zeng,et al.  Facile synthesis and photochromic properties of diarylethene-containing terpyridine and its transition metal (Zn2+/Co2+/Ru2+) complexes , 2012 .

[152]  Tyler B. Norsten,et al.  Axially Coordinated Porphyrinic Photochromes for Non‐destructive Information Processing , 2001 .

[153]  Fanyong Yan,et al.  Recognition Preference of Rhodamine Derivative Bearing Phthalimido Gly for by UV-Vis and Fluorescence Spectroscopy , 2013 .

[154]  Y. Kusano,et al.  A new “switched-on” crown ether which exhibits a reversible all-or-none ion-binding ability , 1982 .

[155]  James T. C. Wojtyk,et al.  Modulation of the Spiropyran−Merocyanine Reversion via Metal-Ion Selective Complexation: Trapping of the “Transient” cis-Merocyanine , 2001 .

[156]  R. H. Mitchell,et al.  Effective aromaticity of tricarbonylchromiumbenzene, about 25 enhanced over that of benzene: structural evidence from a complexed benzannulene. , 2002, Journal of the American Chemical Society.

[157]  K. Kimura,et al.  Cation Complexation, Photochromism, and Photoresponsive Ion-Conducting Behavior of Crowned Spirobenzopyran Vinyl Polymers , 2004 .

[158]  D. Qu,et al.  Coordination-assembly for quantitative construction of bis-branched molecular shuttles. , 2011, Organic & biomolecular chemistry.

[159]  H. Tian,et al.  Enhanced photochromism of 1,2-dithienylcyclopentene complexes with metal ion. , 2003, Organic & biomolecular chemistry.

[160]  S. Shinkai,et al.  A Photochemically “Switched‐on” Crown Ether Containing an Intraannular 4‐Methoxyphenylazo Substituent , 1985 .

[161]  A. Louie,et al.  Multimodal magnetic-resonance/optical-imaging contrast agent sensitive to NADH. , 2009, Angewandte Chemie.

[162]  H. Nishihara,et al.  Reversible photoelectronic signal conversion based on photoisomerization-controlled coordination change of azobenzene-bipyridine ligands to copper. , 2005, Journal of the American Chemical Society.

[163]  D. Diamond,et al.  Novel synthesis and characterisation of 3,3-dimethyl-5′-(2-benzothiazolyl)-spironaphth(indoline-2,3′-[3H]naphth[2,1-b] [1,4]oxazine) derivatives , 2009 .

[164]  Minghui Liu,et al.  A New Rhodamine B-coumarin Fluorochrome for Colorimetric Recognition of Cu 2+ and Fluorescent Recognition of Fe3+ in Aqueous Media , 2011 .

[165]  Jin-Gou Xu,et al.  Switching the recognition preference of rhodamine B spirolactam by replacing one atom: design of rhodamine B thiohydrazide for recognition of Hg(II) in aqueous solution. , 2006, Organic letters.

[166]  Lixin Wu,et al.  Syntheses, Crystal Structure, and Photochromic Properties of Rhenium(I) Complexes Containing the Spironaphthoxazine Moiety , 2000 .

[167]  O. Fedorova,et al.  Spironaphtoxazines produced from crown-containing dihydroisoquinolines: Synthesis and spectroscopic study of cation-dependent photochromism , 2007 .

[168]  M. Maekawa,et al.  A MLCT-switched photochromic copper(II) coordination polymer with 1,2-bis(2′-methyl-5′-(4″-pyridyl)-3′-thienyl)perfluorocyclopentene in crystalline phase , 2007 .

[169]  Jianlong Xia,et al.  Synthesis of diarylethene derivatives containing various heterocycles and tuning of light-emitting properties in a turn-on fluorescent diarylethene system , 2011 .

[170]  Hong Zheng,et al.  Ring expansion of spiro-thiolactam in rhodamine scaffold: switching the recognition preference by adding one atom. , 2012, Organic letters.

[171]  H. Tian,et al.  Near-infrared photochromic diarylethene iridium (III) complex. , 2009, Organic letters.

[172]  V. Yam,et al.  Triplet MLCT photosensitization of the ring-closing reaction of diarylethenes by design and synthesis of a photochromic rhenium(I) complex of a diarylethene-containing 1,10-phenanthroline ligand. , 2006, Chemistry.

[173]  Vincenzo Balzani,et al.  Photochemical molecular devices , 2003, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[174]  Vladimir I Minkin,et al.  Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds. , 2004, Chemical reviews.

[175]  Pier Luigi Gentili,et al.  Supramolecular interaction of a spirooxazine with amino acids , 2007 .

[176]  P. Espinet,et al.  Photosensitive azobispyridine gold(I) and silver(I) complexes. , 2011, Dalton transactions.

[177]  H. Nishihara,et al.  Novel Photoisomerization of Azoferrocene with a Low-Energy MLCT Band and Significant Change of the Redox Behavior between the cis- and trans-Isomers , 2000 .

[178]  S. Lippard,et al.  A highly selective turn-on colorimetric, red fluorescent sensor for detecting mobile zinc in living cells. , 2010, Inorganic chemistry.

[179]  Jinhee Park,et al.  Reversible alteration of CO2 adsorption upon photochemical or thermal treatment in a metal-organic framework. , 2012, Journal of the American Chemical Society.

[180]  V. Yam,et al.  Synthesis, photophysics and photochemistry of novel luminescent rhenium(I) photoswitchable materials , 1995 .

[181]  Seiji Shinkai,et al.  Photocontrolled extraction ability of azobenzene-bridged azacrown ether , 1979 .

[182]  Deqing Zhang,et al.  Concatenation of two molecular switches via a Fe(II)/Fe(III) couple. , 2004, Organic letters.

[183]  Kawai Stephen,et al.  PHOTOCHROMIC BIS(MONOAZA-CROWN ETHER)S. ALKALI-METAL CATION COMPLEXING PROPERTIES OF NOVEL DIARYLETHENES , 1998 .

[184]  Hui Liu,et al.  Rhodamine-based derivatives for Cu2+ sensing: spectroscopic studies, structure-recognition relationships and its test strips. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[185]  M. Sugimoto,et al.  Photon-, electron-, and proton-induced isomerization behavior of ferrocenylazobenzenes. , 2005, Inorganic chemistry.

[186]  Seiji Shinkai,et al.  Photoresponsive crown ethers. 2. Photocontrol of ion extraction and ion transport by a bis(crown ether) with a butterfly-like motion , 1981 .

[187]  Fernando Pina,et al.  A novel fluorescent chemosensor exhibiting exciplex emission. An example of an elementary molecular machine driven by pH and by light , 2000 .

[188]  V. Yam,et al.  Photochromic diarylethene-containing ionic liquids and N-heterocyclic carbenes. , 2009, Journal of the American Chemical Society.

[189]  M. Sugimoto,et al.  Redox-conjugated reversible isomerization of ferrocenylazobenzene with a single green light. , 2002, Journal of the American Chemical Society.

[190]  C. McCoy,et al.  A molecular photoionic AND gate based on fluorescent signalling , 1993, Nature.

[191]  H. Tian,et al.  Synthesis and photochromism of a new binuclear porphyrazinato magnesium(II) , 2004 .

[192]  Jun Feng Zhang,et al.  Naphthalimide modified rhodamine derivative: ratiometric and selective fluorescent sensor for Cu2+ based on two different approaches. , 2010, Organic letters.

[193]  Xiaofeng Song,et al.  Cu2+-selective “Off–On” chemsensor based on the rhodamine derivative bearing 8-hydroxyquinoline moiety and its application in live cell imaging , 2013 .

[194]  C. Lodeiro,et al.  Luminescent and chromogenic molecular probes based on polyamines and related compounds , 2009 .

[195]  Lixin Wu,et al.  Synthesis, photophysical, photochemical and electrochemical properties of rhenium(I) diimine complexes with photoisomerizable pyridyl-azo, -ethenyl or -ethyl ligands , 1998 .

[196]  D. Qu,et al.  A ferrocene-functionalized [2]rotaxane with two fluorophores as stoppers. , 2013, The Journal of organic chemistry.

[197]  C. Aakeröy,et al.  The role of metal ions and counterions in the switching behavior of a carboxylic acid functionalized spiropyran. , 2010, Dalton transactions.

[198]  C. Daniel,et al.  trans-cis Photoisomerization of the styrylpyridine Ligand in [Re(CO)3(2,2'-bipyridine)(t-4-styrylpyridine)]+: role of the metal-to-ligand charge-transfer excited states. , 2006, Chemistry.

[199]  F. Pina,et al.  Electrochromic and magnetic ionic liquids. , 2011, Chemical communications.

[200]  Hyunbong Choi,et al.  Photoregulated fluorescence switching in axially coordinated tin(IV) porphyrinic dithienylethene. , 2008, Inorganic chemistry.

[201]  Shinichiro Nakamura,et al.  Thermally irreversible photochromic systems: a theoretical study , 1988 .

[202]  H. Nishihara,et al.  Redox-assisted ring closing reaction of the photogenerated cyclophanediene form of bis(ferrocenyl)dimethyldihydropyrene with interferrocene electronic communication switching. , 2008, Journal of the American Chemical Society.

[203]  R. Schmehl,et al.  Intersystem crossing to both ligand-localized and charge-transfer excited states in mononuclear and dinuclear ruthenium(II) diimine complexes , 1990 .

[204]  Jong Seung Kim,et al.  Tren-spaced rhodamine and pyrene fluorophores: Excimer modulation with metal ion complexation , 2009 .

[205]  Seiji Shinkai,et al.  A photoresponsive cylindrical ionophore , 1982 .

[206]  Cheng Yao,et al.  A highly sensitive and selective ratiometric and colorimetric sensor for Hg2+ based on a rhodamine–nitrobenzoxadiazole conjugate , 2011 .

[207]  P. V. Leeuwen,et al.  Light Switches the Ligand! Photochromic Azobenzene–Phosphanes , 2010 .

[208]  C. Bohne,et al.  High-contrast fluorescence switching using a photoresponsive dithienylethene coordination compound , 2008 .

[209]  Dress,et al.  A photochemically driven molecular-level abacus , 2000, Chemistry.

[210]  M. Irie,et al.  Photoresponsive cesium ion tweezers with a photochromic dithienylethene , 1998 .

[211]  J. Otsuki,et al.  Light-triggered Luminescence Modulation Using Labile Axial Coordination to Zinc–Porphyrin , 2004 .

[212]  H. Tian,et al.  Effective non-destructive readout of photochromic bisthienylethene–phthalocyanine hybrid , 2007 .

[213]  J. Lallemand,et al.  FIRST LIGAND-DRIVEN LIGHT-INDUCED SPIN CHANGE AT ROOM TEMPERATURE IN A TRANSITION-METAL MOLECULAR COMPOUND , 1999 .

[214]  Ji Eun Park,et al.  Molecular tweezer based on zinc porphyrin-substituted diarylethene. , 2007, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[215]  M. Paquette,et al.  Incorporating optical bistability into a magnetically bistable system: a photochromic redox isomeric complex. , 2009, Chemical communications.

[216]  Tatsuya Kato,et al.  Photo-reversible Pb2+-complexation of thermosensitive poly(N-isopropyl acrylamide-co-spiropyran acrylate) in water. , 2004, Chemical communications.

[217]  Jenny Nelson,et al.  Using Self‐Assembling Dipole Molecules to Improve Charge Collection in Molecular Solar Cells , 2006 .

[218]  Gopal Das,et al.  NIR- and FRET-based sensing of Cu2+ and S2- in physiological conditions and in live cells. , 2013, Inorganic chemistry.

[219]  Xiaoling Zhang,et al.  A copper(II) rhodamine complex with a tripodal ligand as a highly selective fluorescence imaging agent for nitric oxide. , 2011, Chemical communications.

[220]  R. H. Mitchell,et al.  A photochromic, electrochromic, thermochromic Ru complexed benzannulene: an organometallic example of the dimethyldihydropyrene-metacyclophanediene valence isomerization. , 2003, Journal of the American Chemical Society.

[221]  S. Fukuzumi,et al.  Synthesis and structural, electrochemical, and optical properties of Ru(II) complexes with azobis(2,2'-bipyridine)s. , 2003, Inorganic chemistry.

[222]  A. Bianchi,et al.  Modulation of the ligational properties of a new cylindrical macrotricycle by coupling of photochemical- and pH-switching properties , 1998 .

[223]  A. Deronzier,et al.  Photochromic and redox properties of bisterpyridine ruthenium complexes based on dimethyldihydropyrene units as bridging ligands. , 2011, Inorganic chemistry.

[224]  Dermot Diamond,et al.  Spiropyran modified micro-fluidic chip channels as photonically controlled self-indicating system for metal ion accumulation and release , 2009 .

[225]  M. Sukwattanasinitt,et al.  New Azobenzene Crown p‐tert‐Butylcalix[4]arenes as Switchable Receptors for Na+ and K+ Ions: Synthesis and Isomerization Studies. , 2001 .

[226]  G. Shen,et al.  Efficient fluorescence resonance energy transfer-based ratiometric fluorescent cellular imaging probe for Zn(2+) using a rhodamine spirolactam as a trigger. , 2010, Analytical chemistry.

[227]  G. Guirado,et al.  Electrochemical Remote Control for Dithienylethene-Ferrocene Switches , 2007 .

[228]  B. Gallois,et al.  Toward Ligand-Driven Light-Induced Spin Changing. Influence of the Configuration of 4 Styrylpyridine (stpy) on the Magnetic Properties of FeII(stpy)4(NCS)2 Complexes. Crystal Structures of the Spin-Crossover Species Fe(trans-stpy)4(NCS)2 and of the High-Spin Species Fe(cis-stpy)4(NCS)2 , 1994 .

[229]  I. Romero,et al.  Electron-, proton-, and photon-induced spectroscopic changes in chromophore-quencher tricarbonyl(2,2'-bipyridine)rhenium(I) complexes with 4,4'-azobis(pyridine). , 2010, Inorganic chemistry.

[230]  D. Whitten,et al.  Photoreactions of transition metal complexes. Ligand reactivity as a probe for excited-state characterization , 1973 .

[231]  H. Tian,et al.  Novel Photochromic Tetraazaporphyrin Mg (II) Containing Bisthienylethene , 2005 .

[232]  Qingbiao Yang,et al.  Rhodamine-based highly sensitive colorimetric off-on fluorescent chemosensor for Hg2+ in aqueous solution and for live cell imaging. , 2011, Organic & biomolecular chemistry.

[233]  M. Baroncini,et al.  Photoswitchable metal coordinating tweezers operated by light-harvesting dendrimers. , 2012, Journal of the American Chemical Society.

[234]  K. Ueno,et al.  Azo-crown ethers. The dyes with azo group directly involved in the crown ether skeleton. , 1980 .

[235]  Hiroyuki Nakazumi,et al.  New Crown Spirobenzopyrans as Light- and Ion-Responsive Dual-Mode Signal Transducers , 1997 .

[236]  Y. Oka,et al.  Structure of silver(I) complex prepared from azobenzenonaphthalenophane, photochemical coordination change of silver(I) and silver(I)-induced acceleration of Z-E thermal isomerization of azobenzene unit. , 2010, Inorganic chemistry.

[237]  Antonio Camara,et al.  Multiresponsive chromogenic systems operated by light and electrical inputs , 2009 .

[238]  Jason Locklin,et al.  Spectroscopic analysis of metal ion binding in spiropyran containing copolymer thin films. , 2010, Analytical chemistry.

[239]  R. Herges,et al.  Light-driven coordination-induced spin-state switching: rational design of photodissociable ligands. , 2012, Chemistry.

[240]  K. Schanze,et al.  Intramolecular Energy Transfer to trans-Stilbene† , 1998 .

[241]  R. McDonald,et al.  Synthesis and coordination chemistry of a photoswitchable bis(phosphine) ligand. , 2005, Inorganic chemistry.